5-Cyclo-pentyl-2-(4-fluoro-phen-yl)-3-isopropyl-sulfonyl-1-benzofuran.

In the title compound, C22H23FO3S, the cyclo-pentyl ring adopts an envelope conformation with the flap atom connected to the benzofuran residue. The 4-fluoro-phenyl ring makes a dihedral angle of 43.67 (3)° with the mean plane [r.m.s. deviation = 0.008 (1) Å] of the benzofuran fragment. In the crystal, mol-ecules are linked by weak C-H⋯O and C-H⋯π inter-actions, forming a three--dimensional network. The crystal structure also exhibits slipped π-π inter-actions between the benzene and furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.883 (2) Å and slippage = 1.731 (2) Å].

Related literature

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

Experimental

Crystal data

C22H23FO3S

M = 386.46

Monoclinic,

a = 9.4736 (3) Å

b = 19.6185 (7) Å

c = 10.8018 (3) Å

β = 108.833 (1)°

V = 1900.12 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 173 K

0.40 × 0.39 × 0.36 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.678, T max = 0.746

18610 measured reflections

4714 independent reflections

3948 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.103

S = 1.03

4714 reflections

246 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.35 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) global, I. DOI: 10.1107/S1600536812045916/fy2075sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812045916/fy2075Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812045916/fy2075Isup3.cml

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

C22H23FO3S	F(000) = 816
Mr = 386.46	Dx = 1.351 Mg m−3
Monoclinic, P21/n	Melting point = 397–398 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 9.4736 (3) Å	Cell parameters from 5864 reflections
b = 19.6185 (7) Å	θ = 2.3–28.0°
c = 10.8018 (3) Å	µ = 0.20 mm−1
β = 108.833 (1)°	T = 173 K
V = 1900.12 (10) Å3	Block, colourless
Z = 4	0.40 × 0.39 × 0.36 mm

Bruker SMART APEXII CCD diffractometer	4714 independent reflections
Radiation source: rotating anode	3948 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.030
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 2.1°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −22→26
Tmin = 0.678, Tmax = 0.746	l = −14→14
18610 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)] = 0.040	Hydrogen site location: difference Fourier map
wR(F2) = 0.103	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0509P)2 + 0.6277P] where P = (Fo2 + 2Fc2)/3
4714 reflections	(Δ/σ)max = 0.001
246 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.35 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.

	x	y	z	Uiso*/Ueq
S1	0.81280 (3)	0.528906 (17)	0.27421 (3)	0.02105 (10)
F1	0.90366 (12)	0.18165 (5)	0.46703 (11)	0.0459 (3)
O1	0.48867 (10)	0.43110 (5)	0.35291 (10)	0.0264 (2)
O2	0.93832 (11)	0.48394 (5)	0.32355 (11)	0.0299 (2)
O3	0.83351 (11)	0.60006 (5)	0.30821 (10)	0.0297 (2)
C1	0.66190 (14)	0.50030 (7)	0.31937 (13)	0.0215 (3)
C2	0.53071 (14)	0.54131 (7)	0.30820 (13)	0.0217 (3)
C3	0.49027 (15)	0.60966 (7)	0.28294 (13)	0.0235 (3)
H3	0.5589	0.6419	0.2697	0.028*
C4	0.34694 (15)	0.62964 (7)	0.27761 (13)	0.0251 (3)
C5	0.24785 (15)	0.58109 (8)	0.29843 (14)	0.0275 (3)
H5	0.1506	0.5955	0.2939	0.033*
C6	0.28562 (15)	0.51320 (8)	0.32526 (14)	0.0280 (3)
H6	0.2180	0.4809	0.3399	0.034*
C7	0.42847 (15)	0.49561 (7)	0.32929 (14)	0.0238 (3)
C8	0.63093 (14)	0.43500 (7)	0.34624 (13)	0.0229 (3)
C9	0.29291 (16)	0.70217 (8)	0.24587 (15)	0.0292 (3)
H9	0.2007	0.7076	0.2709	0.035*
C10	0.2528 (2)	0.72112 (9)	0.10096 (16)	0.0411 (4)
H10A	0.3331	0.7074	0.0660	0.049*
H10B	0.1587	0.6988	0.0487	0.049*
C11	0.2353 (2)	0.79875 (9)	0.09816 (17)	0.0416 (4)
H11A	0.1295	0.8115	0.0807	0.050*
H11B	0.2706	0.8190	0.0295	0.050*
C12	0.3312 (2)	0.82331 (9)	0.2342 (2)	0.0471 (5)
H12A	0.4107	0.8543	0.2271	0.057*
H12B	0.2692	0.8479	0.2778	0.057*
C13	0.3992 (2)	0.75922 (9)	0.31167 (18)	0.0424 (4)
H13A	0.5003	0.7506	0.3070	0.051*
H13B	0.4056	0.7639	0.4046	0.051*
C14	0.70929 (15)	0.36969 (7)	0.37007 (14)	0.0241 (3)
C15	0.85560 (16)	0.36436 (7)	0.45435 (14)	0.0256 (3)
H15	0.9103	0.4044	0.4896	0.031*
C16	0.92156 (16)	0.30085 (8)	0.48691 (15)	0.0298 (3)
H16	1.0204	0.2966	0.5456	0.036*
C17	0.83981 (18)	0.24418 (8)	0.43187 (16)	0.0323 (3)
C18	0.69763 (19)	0.24717 (8)	0.34516 (16)	0.0347 (3)
H18	0.6461	0.2069	0.3069	0.042*
C19	0.63156 (17)	0.31065 (8)	0.31509 (15)	0.0306 (3)
H19	0.5325	0.3141	0.2566	0.037*
C20	0.74619 (16)	0.52264 (8)	0.09910 (14)	0.0292 (3)
H20	0.6493	0.5477	0.0655	0.035*
C21	0.7201 (2)	0.44906 (10)	0.05634 (18)	0.0481 (5)
H21A	0.6878	0.4466	−0.0394	0.072*
H21B	0.6426	0.4296	0.0878	0.072*
H21C	0.8128	0.4233	0.0929	0.072*
C22	0.8593 (2)	0.55731 (9)	0.04609 (17)	0.0410 (4)
H22A	0.9560	0.5344	0.0810	0.061*
H22B	0.8698	0.6053	0.0729	0.061*
H22C	0.8246	0.5545	−0.0496	0.061*

	U11	U22	U33	U12	U13	U23
S1	0.01823 (16)	0.01971 (18)	0.02505 (17)	−0.00166 (12)	0.00676 (12)	−0.00080 (12)
F1	0.0517 (6)	0.0212 (5)	0.0596 (7)	0.0103 (4)	0.0106 (5)	0.0027 (4)
O1	0.0223 (5)	0.0215 (5)	0.0367 (6)	−0.0023 (4)	0.0113 (4)	0.0004 (4)
O2	0.0193 (5)	0.0320 (6)	0.0380 (6)	0.0034 (4)	0.0090 (4)	0.0067 (5)
O3	0.0314 (5)	0.0216 (5)	0.0373 (6)	−0.0074 (4)	0.0124 (4)	−0.0046 (4)
C1	0.0190 (6)	0.0198 (6)	0.0253 (6)	−0.0007 (5)	0.0065 (5)	−0.0015 (5)
C2	0.0196 (6)	0.0228 (7)	0.0225 (6)	−0.0011 (5)	0.0063 (5)	−0.0020 (5)
C3	0.0231 (6)	0.0216 (7)	0.0260 (7)	−0.0002 (5)	0.0082 (5)	−0.0008 (5)
C4	0.0245 (6)	0.0257 (7)	0.0244 (7)	0.0026 (5)	0.0066 (5)	−0.0035 (5)
C5	0.0199 (6)	0.0332 (8)	0.0298 (7)	0.0020 (6)	0.0087 (5)	−0.0046 (6)
C6	0.0223 (7)	0.0302 (8)	0.0329 (7)	−0.0040 (6)	0.0110 (6)	−0.0028 (6)
C7	0.0235 (6)	0.0204 (7)	0.0270 (7)	−0.0007 (5)	0.0077 (5)	−0.0010 (5)
C8	0.0202 (6)	0.0228 (7)	0.0256 (7)	−0.0025 (5)	0.0071 (5)	−0.0029 (5)
C9	0.0256 (7)	0.0268 (8)	0.0355 (8)	0.0056 (6)	0.0103 (6)	−0.0023 (6)
C10	0.0478 (10)	0.0339 (9)	0.0335 (9)	0.0123 (8)	0.0018 (7)	−0.0007 (7)
C11	0.0459 (10)	0.0343 (10)	0.0449 (10)	0.0155 (8)	0.0150 (8)	0.0075 (7)
C12	0.0444 (10)	0.0260 (9)	0.0634 (12)	0.0050 (7)	0.0070 (9)	−0.0025 (8)
C13	0.0415 (9)	0.0304 (9)	0.0444 (10)	0.0063 (7)	−0.0014 (7)	−0.0084 (7)
C14	0.0269 (7)	0.0188 (7)	0.0272 (7)	−0.0003 (5)	0.0098 (5)	0.0003 (5)
C15	0.0266 (7)	0.0218 (7)	0.0287 (7)	−0.0017 (5)	0.0092 (6)	−0.0014 (6)
C16	0.0287 (7)	0.0277 (8)	0.0321 (8)	0.0025 (6)	0.0083 (6)	0.0012 (6)
C17	0.0413 (8)	0.0188 (7)	0.0381 (8)	0.0067 (6)	0.0148 (7)	0.0020 (6)
C18	0.0412 (9)	0.0200 (8)	0.0394 (9)	−0.0042 (6)	0.0082 (7)	−0.0051 (6)
C19	0.0298 (7)	0.0233 (7)	0.0346 (8)	−0.0019 (6)	0.0047 (6)	−0.0026 (6)
C20	0.0290 (7)	0.0333 (8)	0.0239 (7)	0.0019 (6)	0.0065 (6)	−0.0006 (6)
C21	0.0667 (12)	0.0422 (11)	0.0345 (9)	−0.0129 (9)	0.0150 (8)	−0.0137 (8)
C22	0.0479 (10)	0.0459 (10)	0.0356 (9)	−0.0007 (8)	0.0225 (7)	0.0012 (7)

S1—O2	1.4377 (10)	C11—H11A	0.9900
S1—O3	1.4406 (11)	C11—H11B	0.9900
S1—C1	1.7455 (13)	C12—C13	1.533 (2)
S1—C20	1.7946 (14)	C12—H12A	0.9900
F1—C17	1.3663 (17)	C12—H12B	0.9900
O1—C8	1.3749 (15)	C13—H13A	0.9900
O1—C7	1.3776 (17)	C13—H13B	0.9900
C1—C8	1.3661 (19)	C14—C15	1.395 (2)
C1—C2	1.4526 (18)	C14—C19	1.398 (2)
C2—C7	1.3916 (18)	C15—C16	1.387 (2)
C2—C3	1.3971 (19)	C15—H15	0.9500
C3—C4	1.3965 (18)	C16—C17	1.375 (2)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.405 (2)	C17—C18	1.371 (2)
C4—C9	1.514 (2)	C18—C19	1.385 (2)
C5—C6	1.385 (2)	C18—H18	0.9500
C5—H5	0.9500	C19—H19	0.9500
C6—C7	1.3836 (18)	C20—C21	1.511 (2)
C6—H6	0.9500	C20—C22	1.528 (2)
C8—C14	1.4613 (19)	C20—H20	1.0000
C9—C13	1.520 (2)	C21—H21A	0.9800
C9—C10	1.533 (2)	C21—H21B	0.9800
C9—H9	1.0000	C21—H21C	0.9800
C10—C11	1.531 (2)	C22—H22A	0.9800
C10—H10A	0.9900	C22—H22B	0.9800
C10—H10B	0.9900	C22—H22C	0.9800
C11—C12	1.534 (3)
O2—S1—O3	118.15 (6)	C13—C12—C11	106.26 (14)
O2—S1—C1	110.68 (6)	C13—C12—H12A	110.5
O3—S1—C1	107.26 (6)	C11—C12—H12A	110.5
O2—S1—C20	108.42 (7)	C13—C12—H12B	110.5
O3—S1—C20	107.92 (7)	C11—C12—H12B	110.5
C1—S1—C20	103.38 (7)	H12A—C12—H12B	108.7
C8—O1—C7	107.06 (10)	C9—C13—C12	104.50 (13)
C8—C1—C2	107.48 (11)	C9—C13—H13A	110.9
C8—C1—S1	127.76 (10)	C12—C13—H13A	110.9
C2—C1—S1	123.69 (10)	C9—C13—H13B	110.9
C7—C2—C3	119.27 (12)	C12—C13—H13B	110.9
C7—C2—C1	104.57 (12)	H13A—C13—H13B	108.9
C3—C2—C1	136.16 (12)	C15—C14—C19	119.42 (13)
C4—C3—C2	118.62 (13)	C15—C14—C8	121.46 (13)
C4—C3—H3	120.7	C19—C14—C8	118.93 (13)
C2—C3—H3	120.7	C16—C15—C14	120.27 (13)
C3—C4—C5	119.61 (13)	C16—C15—H15	119.9
C3—C4—C9	121.76 (13)	C14—C15—H15	119.9
C5—C4—C9	118.61 (12)	C17—C16—C15	118.14 (14)
C6—C5—C4	122.97 (13)	C17—C16—H16	120.9
C6—C5—H5	118.5	C15—C16—H16	120.9
C4—C5—H5	118.5	F1—C17—C18	118.51 (14)
C7—C6—C5	115.49 (13)	F1—C17—C16	117.95 (14)
C7—C6—H6	122.3	C18—C17—C16	123.54 (14)
C5—C6—H6	122.3	C17—C18—C19	117.95 (14)
O1—C7—C6	125.26 (13)	C17—C18—H18	121.0
O1—C7—C2	110.72 (11)	C19—C18—H18	121.0
C6—C7—C2	124.02 (13)	C18—C19—C14	120.62 (14)
C1—C8—O1	110.16 (12)	C18—C19—H19	119.7
C1—C8—C14	136.71 (12)	C14—C19—H19	119.7
O1—C8—C14	113.13 (11)	C21—C20—C22	112.09 (14)
C4—C9—C13	117.50 (13)	C21—C20—S1	110.77 (11)
C4—C9—C10	114.43 (12)	C22—C20—S1	108.30 (11)
C13—C9—C10	101.96 (14)	C21—C20—H20	108.5
C4—C9—H9	107.5	C22—C20—H20	108.5
C13—C9—H9	107.5	S1—C20—H20	108.5
C10—C9—H9	107.5	C20—C21—H21A	109.5
C11—C10—C9	104.54 (13)	C20—C21—H21B	109.5
C11—C10—H10A	110.8	H21A—C21—H21B	109.5
C9—C10—H10A	110.8	C20—C21—H21C	109.5
C11—C10—H10B	110.8	H21A—C21—H21C	109.5
C9—C10—H10B	110.8	H21B—C21—H21C	109.5
H10A—C10—H10B	108.9	C20—C22—H22A	109.5
C10—C11—C12	105.45 (14)	C20—C22—H22B	109.5
C10—C11—H11A	110.7	H22A—C22—H22B	109.5
C12—C11—H11A	110.7	C20—C22—H22C	109.5
C10—C11—H11B	110.7	H22A—C22—H22C	109.5
C12—C11—H11B	110.7	H22B—C22—H22C	109.5
H11A—C11—H11B	108.8
O2—S1—C1—C8	−26.55 (15)	C3—C4—C9—C13	−43.8 (2)
O3—S1—C1—C8	−156.74 (12)	C5—C4—C9—C13	138.05 (15)
C20—S1—C1—C8	89.36 (14)	C3—C4—C9—C10	75.76 (18)
O2—S1—C1—C2	166.81 (11)	C5—C4—C9—C10	−102.40 (16)
O3—S1—C1—C2	36.62 (13)	C4—C9—C10—C11	−168.08 (13)
C20—S1—C1—C2	−77.28 (12)	C13—C9—C10—C11	−40.14 (16)
C8—C1—C2—C7	−0.33 (15)	C9—C10—C11—C12	25.31 (18)
S1—C1—C2—C7	168.63 (10)	C10—C11—C12—C13	−0.8 (2)
C8—C1—C2—C3	179.94 (15)	C4—C9—C13—C12	165.45 (14)
S1—C1—C2—C3	−11.1 (2)	C10—C9—C13—C12	39.50 (17)
C7—C2—C3—C4	−1.0 (2)	C11—C12—C13—C9	−24.25 (19)
C1—C2—C3—C4	178.68 (15)	C1—C8—C14—C15	45.9 (2)
C2—C3—C4—C5	0.4 (2)	O1—C8—C14—C15	−133.59 (13)
C2—C3—C4—C9	−177.73 (13)	C1—C8—C14—C19	−139.22 (17)
C3—C4—C5—C6	0.4 (2)	O1—C8—C14—C19	41.31 (17)
C9—C4—C5—C6	178.60 (13)	C19—C14—C15—C16	−2.3 (2)
C4—C5—C6—C7	−0.5 (2)	C8—C14—C15—C16	172.62 (13)
C8—O1—C7—C6	178.93 (13)	C14—C15—C16—C17	1.3 (2)
C8—O1—C7—C2	−0.37 (15)	C15—C16—C17—F1	−178.20 (13)
C5—C6—C7—O1	−179.33 (13)	C15—C16—C17—C18	1.0 (2)
C5—C6—C7—C2	−0.1 (2)	F1—C17—C18—C19	176.99 (14)
C3—C2—C7—O1	−179.78 (12)	C16—C17—C18—C19	−2.2 (3)
C1—C2—C7—O1	0.43 (15)	C17—C18—C19—C14	1.2 (2)
C3—C2—C7—C6	0.9 (2)	C15—C14—C19—C18	1.0 (2)
C1—C2—C7—C6	−178.88 (13)	C8—C14—C19—C18	−173.99 (14)
C2—C1—C8—O1	0.11 (15)	O2—S1—C20—C21	51.63 (13)
S1—C1—C8—O1	−168.26 (10)	O3—S1—C20—C21	−179.29 (12)
C2—C1—C8—C14	−179.37 (15)	C1—S1—C20—C21	−65.87 (13)
S1—C1—C8—C14	12.3 (3)	O2—S1—C20—C22	−71.66 (12)
C7—O1—C8—C1	0.15 (15)	O3—S1—C20—C22	57.41 (12)
C7—O1—C8—C14	179.77 (11)	C1—S1—C20—C22	170.83 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2i	0.95	2.60	3.3341 (17)	135
C18—H18···O3ii	0.95	2.48	3.2932 (19)	144
C21—H21A···Cg1iii	0.98	2.71	3.693 (2)	177

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2i	0.95	2.60	3.3341 (17)	135
C18—H18⋯O3ii	0.95	2.48	3.2932 (19)	144
C21—H21A⋯Cg1iii	0.98	2.71	3.693 (2)	177

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