5-Cyclo-pentyl-2-methyl-3-(3-methyl-phenyl-sulfon-yl)-1-benzo-furan.

In the title compound, C21H22O3S, the five-membered ring adopts an envelope conformation with the ipso atom deviating by 0.596 (2) Å from the plane through the rest of the ring atoms. The dihedral angle between the mean planes of the benzo-furan and m-tolyl moieties is 78.4 (1)°. In the crystal, mol-ecules related by a glide plane are linked via C-H⋯O hydrogen bonds into chains along the a-axis direction. These chains are in turn connected by C-H⋯π inter-actions into layers parallel to the ac plane.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2012 ▶); Seo et al. (2011 ▶).

Experimental

Crystal data

C21H22O3S

M = 354.45

Orthorhombic,

a = 18.2293 (7) Å

b = 6.1955 (3) Å

c = 15.9471 (8) Å

V = 1801.06 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 173 K

0.58 × 0.20 × 0.14 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.683, T max = 0.746

9604 measured reflections

3543 independent reflections

3115 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.113

S = 1.04

3543 reflections

228 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 1205 Friedel pairs

Absolute structure parameter: 0.00 (9)

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/S1600536814006187/ld2123sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814006187/ld2123Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814006187/ld2123Isup3.cml

CCDC reference: 992719

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

C21H22O3S	Dx = 1.307 Mg m−3
Mr = 354.45	Melting point = 418–417 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3275 reflections
a = 18.2293 (7) Å	θ = 2.6–28.0°
b = 6.1955 (3) Å	µ = 0.20 mm−1
c = 15.9471 (8) Å	T = 173 K
V = 1801.06 (14) Å3	Block, colourless
Z = 4	0.58 × 0.20 × 0.14 mm
F(000) = 752

Bruker SMART APEXII CCD diffractometer	3543 independent reflections
Radiation source: rotating anode	3115 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.031
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 2.2°
φ and ω scans	h = −24→20
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −8→8
Tmin = 0.683, Tmax = 0.746	l = −15→21
9604 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045	H-atom parameters constrained
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.0575P)2 + 0.6298P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3543 reflections	Δρmax = 0.54 e Å−3
228 parameters	Δρmin = −0.24 e Å−3
1 restraint	Absolute structure: Flack (1983), 1205 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (9)

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	0.04477 (3)	0.35807 (10)	0.10257 (5)	0.02864 (15)
O1	0.23298 (10)	0.1800 (3)	0.00693 (12)	0.0330 (4)
O2	0.03032 (9)	0.5860 (3)	0.10602 (17)	0.0364 (4)
O3	−0.00242 (10)	0.2226 (3)	0.05328 (14)	0.0384 (5)
C1	0.13426 (13)	0.3255 (4)	0.06741 (17)	0.0279 (5)
C2	0.19660 (12)	0.4600 (4)	0.08929 (17)	0.0268 (6)
C3	0.20851 (14)	0.6445 (4)	0.13714 (18)	0.0296 (6)
H3	0.1686	0.7160	0.1636	0.035*
C4	0.27969 (14)	0.7230 (4)	0.14570 (18)	0.0307 (6)
C5	0.33751 (12)	0.6156 (4)	0.1049 (2)	0.0350 (6)
H5	0.3859	0.6701	0.1110	0.042*
C6	0.32665 (14)	0.4335 (5)	0.0562 (2)	0.0361 (6)
H6	0.3659	0.3625	0.0285	0.043*
C7	0.25515 (14)	0.3616 (4)	0.05046 (19)	0.0290 (5)
C8	0.15930 (14)	0.1608 (4)	0.01931 (18)	0.0304 (6)
C9	0.29660 (16)	0.9193 (5)	0.1986 (2)	0.0375 (6)
H9	0.3094	1.0402	0.1597	0.045*
C10	0.3623 (2)	0.8851 (7)	0.2584 (3)	0.0622 (11)
H10A	0.3591	0.7436	0.2870	0.075*
H10B	0.4094	0.8935	0.2277	0.075*
C11	0.3549 (2)	1.0726 (8)	0.3217 (3)	0.0695 (12)
H11A	0.3658	1.0215	0.3792	0.083*
H11B	0.3896	1.1900	0.3076	0.083*
C12	0.2784 (2)	1.1510 (7)	0.3164 (3)	0.0742 (14)
H12A	0.2772	1.3006	0.2945	0.089*
H12B	0.2550	1.1488	0.3724	0.089*
C13	0.23894 (19)	0.9984 (8)	0.2568 (3)	0.0744 (15)
H13A	0.2166	0.8769	0.2879	0.089*
H13B	0.1999	1.0754	0.2256	0.089*
C14	0.12535 (16)	−0.0293 (5)	−0.0228 (2)	0.0396 (7)
H14A	0.0774	−0.0591	0.0026	0.059*
H14B	0.1573	−0.1553	−0.0160	0.059*
H14C	0.1190	0.0017	−0.0826	0.059*
C15	0.04614 (13)	0.2588 (5)	0.20576 (18)	0.0293 (6)
C16	0.07316 (15)	0.3898 (5)	0.26988 (19)	0.0325 (6)
H16	0.0892	0.5319	0.2571	0.039*
C17	0.07705 (15)	0.3171 (5)	0.35138 (19)	0.0356 (6)
C18	0.05211 (15)	0.1092 (5)	0.3682 (2)	0.0392 (7)
H18	0.0534	0.0564	0.4241	0.047*
C19	0.02542 (16)	−0.0220 (5)	0.3047 (2)	0.0403 (7)
H19	0.0085	−0.1631	0.3178	0.048*
C20	0.02297 (14)	0.0489 (5)	0.2224 (2)	0.0351 (6)
H20	0.0060	−0.0426	0.1787	0.042*
C21	0.1076 (2)	0.4573 (6)	0.4203 (2)	0.0501 (8)
H21A	0.0697	0.4824	0.4627	0.075*
H21B	0.1234	0.5958	0.3967	0.075*
H21C	0.1497	0.3849	0.4462	0.075*

	U11	U22	U33	U12	U13	U23
S1	0.0223 (2)	0.0339 (3)	0.0297 (3)	−0.0001 (2)	−0.0018 (3)	−0.0038 (3)
O1	0.0291 (9)	0.0375 (10)	0.0324 (11)	0.0016 (8)	0.0024 (8)	−0.0091 (9)
O2	0.0315 (8)	0.0360 (9)	0.0419 (11)	0.0067 (7)	−0.0011 (10)	−0.0003 (12)
O3	0.0270 (9)	0.0482 (11)	0.0399 (12)	−0.0067 (8)	−0.0046 (8)	−0.0062 (10)
C1	0.0255 (11)	0.0322 (13)	0.0259 (13)	0.0005 (10)	−0.0006 (10)	−0.0011 (11)
C2	0.0236 (10)	0.0308 (13)	0.0258 (15)	0.0002 (9)	−0.0010 (9)	0.0047 (11)
C3	0.0276 (12)	0.0312 (14)	0.0299 (15)	0.0006 (10)	0.0005 (10)	−0.0015 (12)
C4	0.0306 (12)	0.0320 (14)	0.0297 (15)	−0.0032 (11)	−0.0063 (11)	0.0053 (12)
C5	0.0251 (10)	0.0423 (14)	0.0374 (15)	−0.0066 (10)	0.0020 (14)	0.0026 (15)
C6	0.0267 (12)	0.0438 (15)	0.0379 (17)	0.0004 (11)	0.0062 (11)	−0.0012 (14)
C7	0.0285 (12)	0.0322 (13)	0.0263 (13)	0.0001 (10)	0.0008 (10)	−0.0004 (12)
C8	0.0300 (12)	0.0339 (14)	0.0275 (15)	0.0005 (11)	0.0010 (11)	0.0014 (11)
C9	0.0447 (15)	0.0306 (14)	0.0374 (17)	−0.0042 (12)	−0.0063 (13)	0.0038 (13)
C10	0.0471 (18)	0.071 (3)	0.068 (3)	0.0007 (18)	−0.0165 (18)	−0.026 (2)
C11	0.054 (2)	0.083 (3)	0.071 (3)	0.004 (2)	−0.016 (2)	−0.040 (2)
C12	0.054 (2)	0.071 (3)	0.098 (4)	−0.0056 (19)	−0.006 (2)	−0.048 (3)
C13	0.0405 (18)	0.081 (3)	0.102 (4)	0.0042 (18)	−0.008 (2)	−0.057 (3)
C14	0.0441 (16)	0.0411 (16)	0.0335 (17)	0.0001 (13)	−0.0023 (13)	−0.0110 (14)
C15	0.0230 (11)	0.0331 (13)	0.0317 (15)	0.0029 (10)	0.0012 (10)	−0.0022 (12)
C16	0.0326 (13)	0.0328 (15)	0.0320 (16)	−0.0003 (11)	0.0037 (12)	−0.0052 (12)
C17	0.0334 (13)	0.0420 (16)	0.0315 (16)	0.0059 (12)	0.0039 (12)	−0.0049 (13)
C18	0.0353 (14)	0.0450 (18)	0.0373 (18)	0.0044 (13)	0.0022 (12)	0.0063 (14)
C19	0.0374 (14)	0.0354 (16)	0.048 (2)	0.0006 (12)	0.0003 (14)	0.0080 (14)
C20	0.0292 (12)	0.0336 (14)	0.0426 (18)	−0.0025 (11)	0.0005 (12)	−0.0045 (13)
C21	0.062 (2)	0.056 (2)	0.0327 (18)	0.0023 (17)	−0.0065 (15)	−0.0102 (16)

S1—O3	1.436 (2)	C11—C12	1.479 (5)
S1—O2	1.4374 (18)	C11—H11A	0.9900
S1—C1	1.737 (2)	C11—H11B	0.9900
S1—C15	1.757 (3)	C12—C13	1.522 (5)
O1—C8	1.363 (3)	C12—H12A	0.9900
O1—C7	1.382 (3)	C12—H12B	0.9900
C1—C8	1.356 (4)	C13—H13A	0.9900
C1—C2	1.451 (3)	C13—H13B	0.9900
C2—C7	1.376 (4)	C14—H14A	0.9800
C2—C3	1.392 (4)	C14—H14B	0.9800
C3—C4	1.392 (4)	C14—H14C	0.9800
C3—H3	0.9500	C15—C20	1.393 (4)
C4—C5	1.406 (4)	C15—C16	1.395 (4)
C4—C9	1.511 (4)	C16—C17	1.377 (4)
C5—C6	1.383 (4)	C16—H16	0.9500
C5—H5	0.9500	C17—C18	1.392 (4)
C6—C7	1.381 (4)	C17—C21	1.507 (4)
C6—H6	0.9500	C18—C19	1.388 (5)
C8—C14	1.490 (4)	C18—H18	0.9500
C9—C13	1.485 (5)	C19—C20	1.384 (5)
C9—C10	1.546 (5)	C19—H19	0.9500
C9—H9	1.0000	C20—H20	0.9500
C10—C11	1.545 (5)	C21—H21A	0.9800
C10—H10A	0.9900	C21—H21B	0.9800
C10—H10B	0.9900	C21—H21C	0.9800
O3—S1—O2	119.03 (12)	C12—C11—H11B	110.3
O3—S1—C1	108.55 (12)	C10—C11—H11B	110.3
O2—S1—C1	107.38 (11)	H11A—C11—H11B	108.6
O3—S1—C15	108.46 (13)	C11—C12—C13	106.1 (3)
O2—S1—C15	108.09 (14)	C11—C12—H12A	110.5
C1—S1—C15	104.38 (12)	C13—C12—H12A	110.5
C8—O1—C7	106.7 (2)	C11—C12—H12B	110.5
C8—C1—C2	107.7 (2)	C13—C12—H12B	110.5
C8—C1—S1	125.89 (19)	H12A—C12—H12B	108.7
C2—C1—S1	126.24 (19)	C9—C13—C12	105.1 (3)
C7—C2—C3	119.3 (2)	C9—C13—H13A	110.7
C7—C2—C1	104.2 (2)	C12—C13—H13A	110.7
C3—C2—C1	136.5 (2)	C9—C13—H13B	110.7
C2—C3—C4	119.1 (2)	C12—C13—H13B	110.7
C2—C3—H3	120.5	H13A—C13—H13B	108.8
C4—C3—H3	120.5	C8—C14—H14A	109.5
C3—C4—C5	119.2 (3)	C8—C14—H14B	109.5
C3—C4—C9	121.7 (3)	H14A—C14—H14B	109.5
C5—C4—C9	119.1 (2)	C8—C14—H14C	109.5
C6—C5—C4	122.6 (2)	H14A—C14—H14C	109.5
C6—C5—H5	118.7	H14B—C14—H14C	109.5
C4—C5—H5	118.7	C20—C15—C16	120.7 (3)
C7—C6—C5	115.8 (2)	C20—C15—S1	120.1 (2)
C7—C6—H6	122.1	C16—C15—S1	119.2 (2)
C5—C6—H6	122.1	C17—C16—C15	121.3 (3)
C2—C7—C6	124.0 (3)	C17—C16—H16	119.4
C2—C7—O1	111.1 (2)	C15—C16—H16	119.4
C6—C7—O1	124.9 (2)	C16—C17—C18	117.9 (3)
C1—C8—O1	110.4 (2)	C16—C17—C21	121.2 (3)
C1—C8—C14	135.2 (2)	C18—C17—C21	120.9 (3)
O1—C8—C14	114.4 (2)	C19—C18—C17	121.0 (3)
C13—C9—C4	118.0 (3)	C19—C18—H18	119.5
C13—C9—C10	102.0 (3)	C17—C18—H18	119.5
C4—C9—C10	113.1 (3)	C20—C19—C18	121.2 (3)
C13—C9—H9	107.7	C20—C19—H19	119.4
C4—C9—H9	107.7	C18—C19—H19	119.4
C10—C9—H9	107.7	C19—C20—C15	117.9 (3)
C11—C10—C9	103.5 (3)	C19—C20—H20	121.1
C11—C10—H10A	111.1	C15—C20—H20	121.1
C9—C10—H10A	111.1	C17—C21—H21A	109.5
C11—C10—H10B	111.1	C17—C21—H21B	109.5
C9—C10—H10B	111.1	H21A—C21—H21B	109.5
H10A—C10—H10B	109.0	C17—C21—H21C	109.5
C12—C11—C10	106.9 (3)	H21A—C21—H21C	109.5
C12—C11—H11A	110.3	H21B—C21—H21C	109.5
C10—C11—H11A	110.3
O3—S1—C1—C8	−17.0 (3)	C7—O1—C8—C1	1.2 (3)
O2—S1—C1—C8	−146.9 (2)	C7—O1—C8—C14	−179.5 (2)
C15—S1—C1—C8	98.5 (3)	C3—C4—C9—C13	13.6 (5)
O3—S1—C1—C2	168.0 (2)	C5—C4—C9—C13	−165.6 (3)
O2—S1—C1—C2	38.1 (3)	C3—C4—C9—C10	132.5 (3)
C15—S1—C1—C2	−76.5 (3)	C5—C4—C9—C10	−46.7 (4)
C8—C1—C2—C7	0.5 (3)	C13—C9—C10—C11	−36.3 (4)
S1—C1—C2—C7	176.3 (2)	C4—C9—C10—C11	−164.1 (3)
C8—C1—C2—C3	−178.2 (3)	C9—C10—C11—C12	19.1 (5)
S1—C1—C2—C3	−2.4 (5)	C10—C11—C12—C13	5.2 (6)
C7—C2—C3—C4	−1.1 (4)	C4—C9—C13—C12	164.8 (3)
C1—C2—C3—C4	177.5 (3)	C10—C9—C13—C12	40.2 (4)
C2—C3—C4—C5	0.8 (4)	C11—C12—C13—C9	−28.9 (5)
C2—C3—C4—C9	−178.4 (3)	O3—S1—C15—C20	17.8 (2)
C3—C4—C5—C6	0.0 (5)	O2—S1—C15—C20	148.1 (2)
C9—C4—C5—C6	179.2 (3)	C1—S1—C15—C20	−97.8 (2)
C4—C5—C6—C7	−0.5 (5)	O3—S1—C15—C16	−164.5 (2)
C3—C2—C7—C6	0.5 (4)	O2—S1—C15—C16	−34.2 (2)
C1—C2—C7—C6	−178.4 (3)	C1—S1—C15—C16	79.9 (2)
C3—C2—C7—O1	179.2 (2)	C20—C15—C16—C17	−0.7 (4)
C1—C2—C7—O1	0.2 (3)	S1—C15—C16—C17	−178.3 (2)
C5—C6—C7—C2	0.3 (5)	C15—C16—C17—C18	−0.9 (4)
C5—C6—C7—O1	−178.2 (3)	C15—C16—C17—C21	178.8 (3)
C8—O1—C7—C2	−0.9 (3)	C16—C17—C18—C19	1.2 (4)
C8—O1—C7—C6	177.7 (3)	C21—C17—C18—C19	−178.6 (3)
C2—C1—C8—O1	−1.1 (3)	C17—C18—C19—C20	0.3 (5)
S1—C1—C8—O1	−176.91 (19)	C18—C19—C20—C15	−1.9 (4)
C2—C1—C8—C14	179.9 (3)	C16—C15—C20—C19	2.1 (4)
S1—C1—C8—C14	4.1 (5)	S1—C15—C20—C19	179.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O3i	0.95	2.49	3.263 (3)	139
C13—H13B···Cg1ii	0.99	2.99	3.671 (3)	127

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⋯O3i	0.95	2.49	3.263 (3)	139
C13—H13B⋯Cg1ii	0.99	2.99	3.671 (3)	127

Symmetry codes: (i) ; (ii) .