1-Cyclo-hexyl-sulfinyl-2-methyl-naphtho-[2,1-b]furan.

In the title compound, C(19)H(20)O(2)S, the cyclo-hexyl ring adopts a chair conformation and the aryl-sulfinyl unit is positioned equatorial relative to the cyclo-hexyl group. In the crystal, mol-ecules are linked through weak inter-molecular C-H⋯O hydrogen bonds. The O atom of the sulfinyl group is disordered over two orientations with site-occupancy factors of 0.923 (3) and 0.077 (3).

Related literature

For the pharmacological activity of naphtho­furan compounds, see: Einhorn et al. (1984 ▶); Hranjec et al. (2003 ▶); Mahadevan & Vaidya (2003 ▶). For structural studies of related 2-methyl­naphtho­[2,1-b]furan derivatives, see: Choi et al. (2006 ▶, 2007 ▶).

Experimental

Crystal data

C19H20O2S

M = 312.41

Monoclinic,

a = 5.8424 (1) Å

b = 19.5900 (3) Å

c = 13.4314 (2) Å

β = 92.649 (1)°

V = 1535.62 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 173 K

0.42 × 0.34 × 0.26 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.916, T max = 0.946

14260 measured reflections

3527 independent reflections

3026 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.104

S = 1.06

3527 reflections

210 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.49 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, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811010981/fl2340sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010981/fl2340Isup2.hkl

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

C19H20O2S	F(000) = 664
Mr = 312.41	Dx = 1.351 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6431 reflections
a = 5.8424 (1) Å	θ = 2.6–27.5°
b = 19.5900 (3) Å	µ = 0.22 mm−1
c = 13.4314 (2) Å	T = 173 K
β = 92.649 (1)°	Block, colourless
V = 1535.62 (4) Å3	0.42 × 0.34 × 0.26 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3527 independent reflections
Radiation source: rotating anode	3026 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.037
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 1.8°
φ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −21→25
Tmin = 0.916, Tmax = 0.946	l = −17→13
14260 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)] = 0.041	Hydrogen site location: difference Fourier map
wR(F2) = 0.104	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0439P)2 + 0.6943P] where P = (Fo2 + 2Fc2)/3
3527 reflections	(Δ/σ)max = 0.001
210 parameters	Δρmax = 0.56 e Å−3
4 restraints	Δρmin = −0.49 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	0.41951 (7)	0.69277 (2)	0.70702 (3)	0.02494 (12)
O1	0.37126 (19)	0.80010 (6)	0.45636 (8)	0.0279 (3)
O2A	0.1985 (2)	0.65645 (7)	0.69667 (10)	0.0324 (4)	0.923 (3)
O2B	0.428 (3)	0.7216 (7)	0.8085 (4)	0.032 (4)	0.077 (3)
C1	0.4458 (3)	0.74856 (8)	0.60361 (11)	0.0217 (3)
C2	0.6184 (3)	0.80058 (8)	0.59149 (11)	0.0223 (3)
C3	0.8144 (3)	0.82508 (8)	0.64850 (12)	0.0240 (3)
C4	0.8863 (3)	0.80032 (9)	0.74330 (12)	0.0275 (4)
H4	0.8002	0.7656	0.7738	0.033*
C5	1.0795 (3)	0.82587 (10)	0.79219 (13)	0.0349 (4)
H5	1.1264	0.8085	0.8559	0.042*
C6	1.2078 (3)	0.87735 (10)	0.74869 (15)	0.0394 (5)
H6	1.3410	0.8947	0.7831	0.047*
C7	1.1428 (3)	0.90261 (9)	0.65739 (15)	0.0363 (4)
H7	1.2316	0.9375	0.6288	0.044*
C8	0.9452 (3)	0.87778 (8)	0.60411 (13)	0.0287 (4)
C9	0.8795 (3)	0.90357 (9)	0.50783 (14)	0.0346 (4)
H9	0.9706	0.9381	0.4796	0.042*
C10	0.6905 (3)	0.88046 (9)	0.45488 (14)	0.0338 (4)
H10	0.6470	0.8981	0.3909	0.041*
C11	0.5645 (3)	0.82935 (8)	0.49987 (12)	0.0261 (3)
C12	0.3020 (3)	0.75066 (8)	0.52147 (12)	0.0245 (3)
C13	0.0955 (3)	0.71211 (9)	0.48597 (13)	0.0312 (4)
H13A	0.1376	0.6791	0.4351	0.047*
H13B	−0.0190	0.7439	0.4572	0.047*
H13C	0.0315	0.6878	0.5421	0.047*
C14	0.6408 (3)	0.63113 (8)	0.67666 (11)	0.0218 (3)
H14	0.7919	0.6552	0.6773	0.026*
C15	0.5947 (3)	0.59934 (8)	0.57445 (12)	0.0266 (3)
H15A	0.6037	0.6350	0.5226	0.032*
H15B	0.4381	0.5799	0.5702	0.032*
C16	0.7685 (3)	0.54320 (9)	0.55551 (13)	0.0298 (4)
H16A	0.7305	0.5217	0.4901	0.036*
H16B	0.9232	0.5635	0.5530	0.036*
C17	0.7697 (3)	0.48904 (9)	0.63642 (14)	0.0337 (4)
H17A	0.8868	0.4541	0.6232	0.040*
H17B	0.6184	0.4663	0.6359	0.040*
C18	0.8223 (3)	0.52122 (9)	0.73821 (13)	0.0331 (4)
H18A	0.9786	0.5408	0.7403	0.040*
H18B	0.8175	0.4856	0.7904	0.040*
C19	0.6489 (3)	0.57741 (9)	0.75944 (12)	0.0294 (4)
H19A	0.4950	0.5569	0.7647	0.035*
H19B	0.6920	0.5995	0.8239	0.035*

	U11	U22	U33	U12	U13	U23
S1	0.0245 (2)	0.0235 (2)	0.0274 (2)	0.00162 (15)	0.00739 (15)	0.00115 (15)
O1	0.0266 (6)	0.0291 (6)	0.0277 (6)	0.0003 (5)	−0.0021 (5)	0.0036 (5)
O2A	0.0207 (7)	0.0343 (8)	0.0425 (8)	−0.0019 (5)	0.0062 (5)	0.0037 (6)
O2B	0.030 (8)	0.022 (8)	0.045 (7)	0.003 (6)	0.003 (6)	0.014 (6)
C1	0.0208 (7)	0.0193 (7)	0.0251 (7)	0.0015 (6)	0.0029 (6)	−0.0013 (6)
C2	0.0225 (7)	0.0188 (7)	0.0259 (7)	0.0019 (6)	0.0042 (6)	−0.0017 (6)
C3	0.0224 (8)	0.0200 (7)	0.0297 (8)	0.0003 (6)	0.0039 (6)	−0.0065 (6)
C4	0.0264 (8)	0.0275 (8)	0.0287 (8)	−0.0014 (7)	0.0018 (6)	−0.0066 (6)
C5	0.0320 (9)	0.0392 (10)	0.0331 (9)	0.0013 (8)	−0.0027 (7)	−0.0119 (8)
C6	0.0266 (9)	0.0409 (11)	0.0504 (11)	−0.0073 (8)	−0.0003 (8)	−0.0200 (9)
C7	0.0291 (9)	0.0293 (9)	0.0510 (11)	−0.0079 (7)	0.0080 (8)	−0.0116 (8)
C8	0.0272 (8)	0.0211 (8)	0.0384 (9)	−0.0012 (7)	0.0078 (7)	−0.0060 (7)
C9	0.0369 (10)	0.0245 (9)	0.0434 (10)	−0.0058 (7)	0.0112 (8)	0.0024 (7)
C10	0.0381 (10)	0.0280 (9)	0.0356 (9)	0.0004 (7)	0.0058 (8)	0.0076 (7)
C11	0.0245 (8)	0.0242 (8)	0.0297 (8)	0.0014 (6)	0.0018 (6)	−0.0004 (6)
C12	0.0235 (8)	0.0229 (8)	0.0274 (8)	0.0024 (6)	0.0033 (6)	−0.0010 (6)
C13	0.0258 (8)	0.0359 (10)	0.0315 (9)	−0.0028 (7)	−0.0015 (7)	−0.0034 (7)
C14	0.0192 (7)	0.0203 (7)	0.0260 (7)	0.0001 (6)	0.0020 (6)	−0.0012 (6)
C15	0.0295 (8)	0.0243 (8)	0.0260 (8)	0.0041 (7)	−0.0007 (6)	−0.0015 (6)
C16	0.0317 (9)	0.0251 (8)	0.0327 (9)	0.0044 (7)	0.0023 (7)	−0.0043 (7)
C17	0.0328 (9)	0.0227 (8)	0.0454 (10)	0.0048 (7)	0.0009 (8)	0.0005 (7)
C18	0.0338 (9)	0.0292 (9)	0.0362 (9)	0.0051 (7)	−0.0013 (7)	0.0074 (7)
C19	0.0314 (9)	0.0289 (9)	0.0279 (8)	0.0019 (7)	0.0023 (7)	0.0034 (7)

S1—O2B	1.4741 (16)	C10—C11	1.397 (2)
S1—O2A	1.4752 (13)	C10—H10	0.9500
S1—C1	1.7796 (16)	C12—C13	1.483 (2)
S1—C14	1.8287 (15)	C13—H13A	0.9800
O1—C11	1.372 (2)	C13—H13B	0.9800
O1—C12	1.3782 (19)	C13—H13C	0.9800
C1—C12	1.356 (2)	C14—C15	1.520 (2)
C1—C2	1.448 (2)	C14—C19	1.530 (2)
C2—C11	1.377 (2)	C14—H14	1.0000
C2—C3	1.431 (2)	C15—C16	1.526 (2)
C3—C4	1.408 (2)	C15—H15A	0.9900
C3—C8	1.431 (2)	C15—H15B	0.9900
C4—C5	1.374 (2)	C16—C17	1.519 (2)
C4—H4	0.9500	C16—H16A	0.9900
C5—C6	1.400 (3)	C16—H16B	0.9900
C5—H5	0.9500	C17—C18	1.524 (3)
C6—C7	1.360 (3)	C17—H17A	0.9900
C6—H6	0.9500	C17—H17B	0.9900
C7—C8	1.416 (2)	C18—C19	1.532 (2)
C7—H7	0.9500	C18—H18A	0.9900
C8—C9	1.424 (3)	C18—H18B	0.9900
C9—C10	1.363 (3)	C19—H19A	0.9900
C9—H9	0.9500	C19—H19B	0.9900
O2B—S1—O2A	105.2 (6)	C12—C13—H13A	109.5
O2B—S1—C1	119.1 (6)	C12—C13—H13B	109.5
O2A—S1—C1	109.24 (8)	H13A—C13—H13B	109.5
O2B—S1—C14	117.8 (6)	C12—C13—H13C	109.5
O2A—S1—C14	106.57 (7)	H13A—C13—H13C	109.5
C1—S1—C14	98.29 (7)	H13B—C13—H13C	109.5
C11—O1—C12	106.44 (12)	C15—C14—C19	111.88 (13)
C12—C1—C2	107.20 (14)	C15—C14—S1	111.98 (11)
C12—C1—S1	125.51 (12)	C19—C14—S1	106.89 (10)
C2—C1—S1	127.28 (12)	C15—C14—H14	108.7
C11—C2—C3	119.04 (14)	C19—C14—H14	108.7
C11—C2—C1	104.89 (14)	S1—C14—H14	108.7
C3—C2—C1	136.07 (15)	C14—C15—C16	110.75 (13)
C4—C3—C2	124.48 (15)	C14—C15—H15A	109.5
C4—C3—C8	118.85 (15)	C16—C15—H15A	109.5
C2—C3—C8	116.67 (15)	C14—C15—H15B	109.5
C5—C4—C3	120.71 (16)	C16—C15—H15B	109.5
C5—C4—H4	119.6	H15A—C15—H15B	108.1
C3—C4—H4	119.6	C17—C16—C15	111.43 (14)
C4—C5—C6	120.46 (18)	C17—C16—H16A	109.3
C4—C5—H5	119.8	C15—C16—H16A	109.3
C6—C5—H5	119.8	C17—C16—H16B	109.3
C7—C6—C5	120.37 (17)	C15—C16—H16B	109.3
C7—C6—H6	119.8	H16A—C16—H16B	108.0
C5—C6—H6	119.8	C16—C17—C18	110.31 (14)
C6—C7—C8	121.19 (17)	C16—C17—H17A	109.6
C6—C7—H7	119.4	C18—C17—H17A	109.6
C8—C7—H7	119.4	C16—C17—H17B	109.6
C7—C8—C9	121.08 (16)	C18—C17—H17B	109.6
C7—C8—C3	118.42 (16)	H17A—C17—H17B	108.1
C9—C8—C3	120.49 (16)	C17—C18—C19	110.89 (14)
C10—C9—C8	122.26 (16)	C17—C18—H18A	109.5
C10—C9—H9	118.9	C19—C18—H18A	109.5
C8—C9—H9	118.9	C17—C18—H18B	109.5
C9—C10—C11	116.30 (16)	C19—C18—H18B	109.5
C9—C10—H10	121.9	H18A—C18—H18B	108.1
C11—C10—H10	121.9	C14—C19—C18	110.95 (13)
O1—C11—C2	111.06 (14)	C14—C19—H19A	109.5
O1—C11—C10	123.70 (15)	C18—C19—H19A	109.5
C2—C11—C10	125.22 (16)	C14—C19—H19B	109.5
C1—C12—O1	110.39 (14)	C18—C19—H19B	109.5
C1—C12—C13	135.26 (15)	H19A—C19—H19B	108.0
O1—C12—C13	114.34 (14)
O2B—S1—C1—C12	−129.3 (7)	C12—O1—C11—C2	−0.83 (17)
O2A—S1—C1—C12	−8.48 (16)	C12—O1—C11—C10	177.79 (15)
C14—S1—C1—C12	102.38 (15)	C3—C2—C11—O1	−179.51 (13)
O2B—S1—C1—C2	49.3 (7)	C1—C2—C11—O1	1.20 (17)
O2A—S1—C1—C2	170.18 (13)	C3—C2—C11—C10	1.9 (2)
C14—S1—C1—C2	−78.96 (14)	C1—C2—C11—C10	−177.40 (16)
C12—C1—C2—C11	−1.11 (17)	C9—C10—C11—O1	−179.38 (15)
S1—C1—C2—C11	−179.96 (12)	C9—C10—C11—C2	−1.0 (3)
C12—C1—C2—C3	179.78 (17)	C2—C1—C12—O1	0.64 (17)
S1—C1—C2—C3	0.9 (3)	S1—C1—C12—O1	179.53 (10)
C11—C2—C3—C4	179.47 (15)	C2—C1—C12—C13	179.33 (17)
C1—C2—C3—C4	−1.5 (3)	S1—C1—C12—C13	−1.8 (3)
C11—C2—C3—C8	−1.3 (2)	C11—O1—C12—C1	0.08 (17)
C1—C2—C3—C8	177.71 (16)	C11—O1—C12—C13	−178.90 (13)
C2—C3—C4—C5	178.74 (15)	O2B—S1—C14—C15	173.0 (7)
C8—C3—C4—C5	−0.5 (2)	O2A—S1—C14—C15	55.20 (13)
C3—C4—C5—C6	0.3 (3)	C1—S1—C14—C15	−57.80 (12)
C4—C5—C6—C7	−0.1 (3)	O2B—S1—C14—C19	50.1 (7)
C5—C6—C7—C8	0.0 (3)	O2A—S1—C14—C19	−67.66 (12)
C6—C7—C8—C9	−179.00 (17)	C1—S1—C14—C19	179.35 (11)
C6—C7—C8—C3	−0.1 (3)	C19—C14—C15—C16	−54.42 (18)
C4—C3—C8—C7	0.3 (2)	S1—C14—C15—C16	−174.40 (11)
C2—C3—C8—C7	−178.92 (14)	C14—C15—C16—C17	56.20 (18)
C4—C3—C8—C9	179.24 (15)	C15—C16—C17—C18	−57.71 (19)
C2—C3—C8—C9	0.0 (2)	C16—C17—C18—C19	57.25 (19)
C7—C8—C9—C10	179.84 (17)	C15—C14—C19—C18	54.40 (18)
C3—C8—C9—C10	1.0 (3)	S1—C14—C19—C18	177.31 (12)
C8—C9—C10—C11	−0.5 (3)	C17—C18—C19—C14	−55.59 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13B···O2Bi	0.98	2.12	2.848 (6)	130
C14—H14···O2Aii	1.00	2.38	3.2947 (19)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13B⋯O2Bi	0.98	2.12	2.848 (6)	130
C14—H14⋯O2Aii	1.00	2.38	3.2947 (19)	152

Symmetry codes: (i) ; (ii) .