5-Cyclo-pentyl-2-methyl-3-(4-methyl-phenyl-sulfon-yl)-1-benzo-furan.

In the title compound, C21H22O3S, the cyclo-pentyl ring adopts a twist conformation. The dihedral angle between the mean planes of the benzo-furan and 4-methyl-phenyl rings is 72.38 (6)°. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯π inter-actions, forming a three-dimensional supra-molecular network.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2012 ▶, 2014 ▶); Seo et al. (2011 ▶).

Experimental

Crystal data

C21H22O3S

M = 354.45

Monoclinic,

a = 10.5452 (7) Å

b = 6.3093 (4) Å

c = 13.7813 (9) Å

β = 91.626 (4)°

V = 916.54 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 173 K

0.42 × 0.25 × 0.23 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.636, T max = 0.746

13479 measured reflections

4144 independent reflections

3276 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.106

S = 1.02

4144 reflections

228 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 2111 Friedel pairs

Absolute structure parameter: 0.02 (6)

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/S160053681400868X/bt6977sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681400868X/bt6977Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681400868X/bt6977Isup3.cml

CCDC reference: 997753

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

C21H22O3S	F(000) = 376
Mr = 354.45	Dx = 1.284 Mg m−3
Monoclinic, Pn	Melting point = 399–398 K
Hall symbol: P -2yac	Mo Kα radiation, λ = 0.71073 Å
a = 10.5452 (7) Å	Cell parameters from 4626 reflections
b = 6.3093 (4) Å	θ = 2.4–22.7°
c = 13.7813 (9) Å	µ = 0.19 mm−1
β = 91.626 (4)°	T = 173 K
V = 916.54 (10) Å3	Block, colourless
Z = 2	0.42 × 0.25 × 0.23 mm

Bruker SMART APEXII CCD diffractometer	4144 independent reflections
Radiation source: rotating anode	3276 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.031
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 2.4°
φ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −8→8
Tmin = 0.636, Tmax = 0.746	l = −17→17
13479 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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.0577P)2 + 0.0503P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
4144 reflections	Δρmax = 0.27 e Å−3
228 parameters	Δρmin = −0.19 e Å−3
2 restraints	Absolute structure: Flack (1983), 2111 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (6)

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	0.50057 (4)	0.43392 (9)	0.52665 (4)	0.04206 (17)
O1	0.81242 (17)	0.5370 (3)	0.38708 (14)	0.0529 (5)
O2	0.46721 (17)	0.2152 (3)	0.53932 (12)	0.0487 (5)
O3	0.52795 (18)	0.5621 (3)	0.61028 (12)	0.0545 (5)
C1	0.6301 (2)	0.4397 (4)	0.45279 (16)	0.0398 (6)
C2	0.6569 (2)	0.2858 (4)	0.37834 (16)	0.0376 (5)
C3	0.5997 (2)	0.1062 (4)	0.34016 (15)	0.0384 (5)
H3	0.5220	0.0571	0.3652	0.046*
C4	0.6558 (2)	−0.0023 (4)	0.26530 (16)	0.0413 (5)
C5	0.7737 (2)	0.0714 (5)	0.23120 (18)	0.0509 (7)
H5	0.8134	−0.0044	0.1809	0.061*
C6	0.8315 (3)	0.2481 (5)	0.2687 (2)	0.0549 (7)
H6	0.9104	0.2961	0.2454	0.066*
C7	0.7714 (2)	0.3539 (4)	0.34139 (17)	0.0454 (6)
C8	0.7251 (2)	0.5865 (4)	0.45435 (18)	0.0461 (6)
C9	0.5876 (3)	−0.1898 (4)	0.22067 (17)	0.0484 (7)
H9	0.5692	−0.2910	0.2743	0.058*
C10	0.6516 (3)	−0.3141 (5)	0.1417 (2)	0.0678 (9)
H10A	0.6880	−0.2181	0.0930	0.081*
H10B	0.7198	−0.4056	0.1693	0.081*
C11	0.5457 (3)	−0.4451 (5)	0.0973 (3)	0.0762 (10)
H11A	0.5624	−0.4774	0.0286	0.091*
H11B	0.5366	−0.5801	0.1331	0.091*
C12	0.4278 (4)	−0.3131 (6)	0.1049 (3)	0.0920 (12)
H12A	0.3581	−0.3981	0.1319	0.110*
H12B	0.4001	−0.2596	0.0401	0.110*
C13	0.4621 (3)	−0.1308 (6)	0.1718 (3)	0.0729 (9)
H13A	0.3962	−0.1109	0.2207	0.087*
H13B	0.4704	0.0022	0.1345	0.087*
C14	0.7537 (3)	0.7785 (5)	0.5121 (2)	0.0636 (8)
H14A	0.8248	0.7497	0.5575	0.095*
H14B	0.6789	0.8187	0.5485	0.095*
H14C	0.7764	0.8945	0.4686	0.095*
C15	0.3770 (2)	0.5572 (4)	0.45880 (16)	0.0404 (6)
C16	0.3159 (2)	0.4485 (4)	0.38343 (19)	0.0461 (6)
H16	0.3406	0.3077	0.3684	0.055*
C17	0.2205 (3)	0.5442 (4)	0.3310 (2)	0.0539 (7)
H17	0.1786	0.4687	0.2798	0.065*
C18	0.1836 (2)	0.7506 (4)	0.3514 (2)	0.0500 (6)
C19	0.2460 (3)	0.8554 (4)	0.4268 (2)	0.0526 (7)
H19	0.2212	0.9958	0.4424	0.063*
C20	0.3435 (3)	0.7610 (4)	0.47994 (19)	0.0478 (6)
H20	0.3868	0.8365	0.5305	0.057*
C21	0.0784 (3)	0.8560 (6)	0.2938 (3)	0.0746 (9)
H21A	0.1139	0.9335	0.2393	0.112*
H21B	0.0337	0.9552	0.3356	0.112*
H21C	0.0188	0.7483	0.2691	0.112*

	U11	U22	U33	U12	U13	U23
S1	0.0520 (4)	0.0414 (3)	0.0326 (3)	−0.0023 (3)	−0.0020 (2)	−0.0036 (3)
O1	0.0435 (9)	0.0531 (12)	0.0617 (12)	−0.0095 (9)	−0.0069 (8)	0.0157 (9)
O2	0.0648 (13)	0.0421 (10)	0.0398 (9)	−0.0044 (8)	0.0089 (8)	0.0024 (8)
O3	0.0726 (13)	0.0552 (12)	0.0354 (9)	−0.0042 (10)	−0.0064 (9)	−0.0070 (8)
C1	0.0431 (13)	0.0395 (15)	0.0361 (12)	−0.0023 (11)	−0.0075 (10)	0.0059 (10)
C2	0.0370 (12)	0.0443 (14)	0.0312 (11)	0.0039 (11)	−0.0035 (9)	0.0098 (10)
C3	0.0384 (12)	0.0453 (15)	0.0315 (11)	0.0076 (11)	0.0007 (9)	0.0075 (10)
C4	0.0455 (13)	0.0443 (13)	0.0339 (12)	0.0141 (11)	−0.0009 (10)	0.0077 (10)
C5	0.0457 (15)	0.065 (2)	0.0422 (14)	0.0167 (14)	0.0082 (11)	0.0120 (13)
C6	0.0406 (14)	0.0626 (18)	0.0619 (17)	0.0033 (14)	0.0077 (12)	0.0175 (14)
C7	0.0388 (13)	0.0531 (16)	0.0440 (14)	0.0042 (12)	−0.0034 (11)	0.0144 (11)
C8	0.0482 (14)	0.0455 (15)	0.0437 (14)	−0.0018 (12)	−0.0158 (12)	0.0130 (11)
C9	0.0685 (17)	0.0446 (16)	0.0321 (12)	0.0170 (14)	0.0002 (12)	0.0029 (10)
C10	0.082 (2)	0.068 (2)	0.0535 (17)	0.0207 (17)	0.0019 (15)	−0.0204 (15)
C11	0.098 (3)	0.061 (2)	0.070 (2)	0.0043 (19)	0.0099 (19)	−0.0236 (16)
C12	0.097 (3)	0.085 (3)	0.094 (3)	0.001 (2)	−0.019 (2)	−0.039 (2)
C13	0.0604 (19)	0.067 (2)	0.090 (2)	0.0147 (16)	−0.0119 (17)	−0.0254 (18)
C14	0.0721 (19)	0.0486 (17)	0.0683 (19)	−0.0122 (14)	−0.0286 (16)	0.0078 (14)
C15	0.0444 (14)	0.0401 (14)	0.0367 (12)	−0.0002 (11)	0.0039 (11)	−0.0027 (10)
C16	0.0471 (14)	0.0407 (15)	0.0503 (14)	0.0025 (12)	−0.0025 (11)	−0.0137 (12)
C17	0.0518 (16)	0.0543 (18)	0.0551 (16)	0.0000 (13)	−0.0071 (13)	−0.0132 (13)
C18	0.0458 (15)	0.0493 (16)	0.0549 (16)	0.0001 (12)	0.0008 (12)	−0.0004 (13)
C19	0.0617 (17)	0.0404 (15)	0.0559 (16)	0.0057 (13)	0.0052 (13)	−0.0074 (13)
C20	0.0610 (17)	0.0391 (15)	0.0433 (14)	−0.0032 (12)	0.0030 (12)	−0.0074 (11)
C21	0.0671 (19)	0.070 (2)	0.086 (2)	0.0110 (16)	−0.0177 (17)	0.0013 (18)

S1—O3	1.4307 (17)	C11—C12	1.502 (5)
S1—O2	1.4358 (18)	C11—H11A	0.9900
S1—C1	1.727 (2)	C11—H11B	0.9900
S1—C15	1.763 (2)	C12—C13	1.512 (4)
O1—C8	1.362 (3)	C12—H12A	0.9900
O1—C7	1.379 (3)	C12—H12B	0.9900
C1—C8	1.364 (3)	C13—H13A	0.9900
C1—C2	1.446 (3)	C13—H13B	0.9900
C2—C3	1.381 (3)	C14—H14A	0.9800
C2—C7	1.392 (3)	C14—H14B	0.9800
C3—C4	1.385 (3)	C14—H14C	0.9800
C3—H3	0.9500	C15—C20	1.367 (3)
C4—C5	1.419 (4)	C15—C16	1.388 (3)
C4—C9	1.507 (4)	C16—C17	1.363 (4)
C5—C6	1.365 (4)	C16—H16	0.9500
C5—H5	0.9500	C17—C18	1.390 (4)
C6—C7	1.373 (4)	C17—H17	0.9500
C6—H6	0.9500	C18—C19	1.383 (4)
C8—C14	1.476 (4)	C18—C21	1.501 (4)
C9—C13	1.514 (4)	C19—C20	1.381 (4)
C9—C10	1.515 (4)	C19—H19	0.9500
C9—H9	1.0000	C20—H20	0.9500
C10—C11	1.505 (5)	C21—H21A	0.9800
C10—H10A	0.9900	C21—H21B	0.9800
C10—H10B	0.9900	C21—H21C	0.9800
O3—S1—O2	119.33 (11)	C12—C11—H11B	110.6
O3—S1—C1	108.55 (11)	C10—C11—H11B	110.6
O2—S1—C1	107.01 (11)	H11A—C11—H11B	108.7
O3—S1—C15	107.88 (11)	C11—C12—C13	106.2 (3)
O2—S1—C15	107.98 (11)	C11—C12—H12A	110.5
C1—S1—C15	105.24 (11)	C13—C12—H12A	110.5
C8—O1—C7	107.06 (19)	C11—C12—H12B	110.5
C8—C1—C2	108.0 (2)	C13—C12—H12B	110.5
C8—C1—S1	126.7 (2)	H12A—C12—H12B	108.7
C2—C1—S1	125.30 (17)	C12—C13—C9	106.0 (3)
C3—C2—C7	119.2 (2)	C12—C13—H13A	110.5
C3—C2—C1	136.8 (2)	C9—C13—H13A	110.5
C7—C2—C1	104.0 (2)	C12—C13—H13B	110.5
C2—C3—C4	119.9 (2)	C9—C13—H13B	110.5
C2—C3—H3	120.1	H13A—C13—H13B	108.7
C4—C3—H3	120.1	C8—C14—H14A	109.5
C3—C4—C5	118.8 (3)	C8—C14—H14B	109.5
C3—C4—C9	118.9 (2)	H14A—C14—H14B	109.5
C5—C4—C9	122.3 (2)	C8—C14—H14C	109.5
C6—C5—C4	121.9 (3)	H14A—C14—H14C	109.5
C6—C5—H5	119.1	H14B—C14—H14C	109.5
C4—C5—H5	119.1	C20—C15—C16	120.5 (2)
C5—C6—C7	117.6 (3)	C20—C15—S1	119.57 (18)
C5—C6—H6	121.2	C16—C15—S1	119.94 (19)
C7—C6—H6	121.2	C17—C16—C15	119.8 (2)
C6—C7—O1	126.5 (2)	C17—C16—H16	120.1
C6—C7—C2	122.6 (3)	C15—C16—H16	120.1
O1—C7—C2	110.8 (2)	C16—C17—C18	121.0 (2)
O1—C8—C1	110.2 (2)	C16—C17—H17	119.5
O1—C8—C14	115.0 (2)	C18—C17—H17	119.5
C1—C8—C14	134.8 (3)	C19—C18—C17	118.0 (2)
C4—C9—C13	112.9 (2)	C19—C18—C21	120.9 (3)
C4—C9—C10	118.9 (3)	C17—C18—C21	121.0 (3)
C13—C9—C10	102.1 (2)	C20—C19—C18	121.6 (3)
C4—C9—H9	107.5	C20—C19—H19	119.2
C13—C9—H9	107.5	C18—C19—H19	119.2
C10—C9—H9	107.5	C15—C20—C19	119.1 (2)
C11—C10—C9	103.6 (3)	C15—C20—H20	120.5
C11—C10—H10A	111.0	C19—C20—H20	120.5
C9—C10—H10A	111.0	C18—C21—H21A	109.5
C11—C10—H10B	111.0	C18—C21—H21B	109.5
C9—C10—H10B	111.0	H21A—C21—H21B	109.5
H10A—C10—H10B	109.0	C18—C21—H21C	109.5
C12—C11—C10	105.9 (3)	H21A—C21—H21C	109.5
C12—C11—H11A	110.6	H21B—C21—H21C	109.5
C10—C11—H11A	110.6
O3—S1—C1—C8	−19.1 (2)	C2—C1—C8—C14	−179.7 (3)
O2—S1—C1—C8	−149.1 (2)	S1—C1—C8—C14	−0.3 (4)
C15—S1—C1—C8	96.2 (2)	C3—C4—C9—C13	63.1 (3)
O3—S1—C1—C2	160.22 (18)	C5—C4—C9—C13	−114.8 (3)
O2—S1—C1—C2	30.2 (2)	C3—C4—C9—C10	−177.4 (2)
C15—S1—C1—C2	−84.5 (2)	C5—C4—C9—C10	4.7 (3)
C8—C1—C2—C3	−178.8 (2)	C4—C9—C10—C11	−165.3 (2)
S1—C1—C2—C3	1.8 (4)	C13—C9—C10—C11	−40.4 (3)
C8—C1—C2—C7	1.1 (2)	C9—C10—C11—C12	32.6 (4)
S1—C1—C2—C7	−178.34 (17)	C10—C11—C12—C13	−11.8 (4)
C7—C2—C3—C4	−0.7 (3)	C11—C12—C13—C9	−13.6 (4)
C1—C2—C3—C4	179.2 (2)	C4—C9—C13—C12	162.1 (3)
C2—C3—C4—C5	1.7 (3)	C10—C9—C13—C12	33.3 (4)
C2—C3—C4—C9	−176.2 (2)	O3—S1—C15—C20	12.7 (2)
C3—C4—C5—C6	−1.4 (3)	O2—S1—C15—C20	142.91 (19)
C9—C4—C5—C6	176.5 (2)	C1—S1—C15—C20	−103.1 (2)
C4—C5—C6—C7	0.0 (4)	O3—S1—C15—C16	−168.37 (19)
C5—C6—C7—O1	−178.5 (2)	O2—S1—C15—C16	−38.1 (2)
C5—C6—C7—C2	1.1 (4)	C1—S1—C15—C16	75.9 (2)
C8—O1—C7—C6	−179.8 (2)	C20—C15—C16—C17	−1.0 (4)
C8—O1—C7—C2	0.6 (2)	S1—C15—C16—C17	−180.0 (2)
C3—C2—C7—C6	−0.8 (3)	C15—C16—C17—C18	0.5 (4)
C1—C2—C7—C6	179.3 (2)	C16—C17—C18—C19	−0.4 (4)
C3—C2—C7—O1	178.86 (19)	C16—C17—C18—C21	−179.9 (3)
C1—C2—C7—O1	−1.0 (2)	C17—C18—C19—C20	1.0 (4)
C7—O1—C8—C1	0.2 (2)	C21—C18—C19—C20	−179.6 (3)
C7—O1—C8—C14	179.3 (2)	C16—C15—C20—C19	1.5 (4)
C2—C1—C8—O1	−0.8 (3)	S1—C15—C20—C19	−179.5 (2)
S1—C1—C8—O1	178.63 (16)	C18—C19—C20—C15	−1.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O3i	0.95	2.44	3.279 (3)	148
C20—H20···O2ii	0.95	2.54	3.244 (3)	131
C9—H9···Cg1iii	1.0	2.89	3.680 (3)	136
C12—H12B···Cg1iv	0.99	2.88	3.591 (3)	129
C14—H14C···Cg2ii	0.98	2.94	3.826 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O3i	0.95	2.44	3.279 (3)	148
C20—H20⋯O2ii	0.95	2.54	3.244 (3)	131
C9—H9⋯Cg1iii	1.0	2.89	3.680 (3)	136
C12—H12B⋯Cg1iv	0.99	2.88	3.591 (3)	129
C14—H14C⋯Cg2ii	0.98	2.94	3.826 (3)	151

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