2-Methyl-1-(4-methyl-phenyl-sulfinyl)naphtho-[2,1-b]furan.

In the title compound, C(20)H(16)O(2)S, the 4-methyl-phenyl ring makes a dihedral angle of 82.60 (4)° with the mean plane [r.m.s. deviation = 0.007 (1) Å] of the naphtho-furan fragment. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O hydrogen bonds, and by a slipped π-π inter-action between the central naphtho-furan benzene rings of neighbouring mol-ecules [centroid-to-centroid distance = 3.671 (2) Å, inter-planar distance = 3.349 (2) Å and slippage = 1.503 (2)°].

Related literature

For the pharmacological activity of naphtho­furan compounds, see: Goel & Dixit (2004 ▶); Hagiwara et al. (1999 ▶); Piloto et al. (2005 ▶). For the crystal structures of related compounds, see: Choi et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C20H16O2S

M = 320.39

Monoclinic,

a = 6.5052 (1) Å

b = 16.7418 (3) Å

c = 14.4935 (2) Å

β = 97.883 (1)°

V = 1563.55 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 173 K

0.28 × 0.28 × 0.26 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.677, T max = 0.746

15390 measured reflections

3896 independent reflections

3271 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.107

S = 1.03

3896 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.39 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 datablock(s) global, I. DOI: 10.1107/S1600536812003121/lr2049sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003121/lr2049Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812003121/lr2049Isup3.cml

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

C20H16O2S	F(000) = 672
Mr = 320.39	Dx = 1.361 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5690 reflections
a = 6.5052 (1) Å	θ = 2.8–28.1°
b = 16.7418 (3) Å	µ = 0.21 mm−1
c = 14.4935 (2) Å	T = 173 K
β = 97.883 (1)°	Block, colourless
V = 1563.55 (4) Å3	0.28 × 0.28 × 0.26 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3896 independent reflections
Radiation source: rotating anode	3271 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.028
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 1.9°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −19→22
Tmin = 0.677, Tmax = 0.746	l = −19→19
15390 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)] = 0.039	Hydrogen site location: difference Fourier map
wR(F2) = 0.107	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0548P)2 + 0.534P] where P = (Fo2 + 2Fc2)/3
3896 reflections	(Δ/σ)max < 0.001
210 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Geometry. Cg···Cgiv distance = 3.671 (2) Å; (iv) -x + 1, -y + 1, -zCg is the centroid of the C2/C3/C8–C11 benzene ring.

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	0.54869 (6)	0.29240 (2)	0.22725 (3)	0.02964 (11)
O1	0.18369 (15)	0.42901 (7)	0.06023 (7)	0.0332 (2)
O2	0.77697 (17)	0.28641 (6)	0.22477 (8)	0.0391 (3)
C1	0.4389 (2)	0.37111 (8)	0.15685 (9)	0.0268 (3)
C2	0.4942 (2)	0.45457 (8)	0.14760 (9)	0.0251 (3)
C3	0.6672 (2)	0.50427 (8)	0.17904 (9)	0.0253 (3)
C4	0.8502 (2)	0.47737 (9)	0.23408 (10)	0.0301 (3)
H4	0.8619	0.4230	0.2528	0.036*
C5	1.0110 (2)	0.52903 (9)	0.26072 (12)	0.0368 (3)
H5	1.1337	0.5100	0.2972	0.044*
C6	0.9958 (2)	0.60987 (9)	0.23450 (12)	0.0375 (4)
H6	1.1067	0.6455	0.2544	0.045*
C7	0.8224 (2)	0.63704 (9)	0.18063 (11)	0.0339 (3)
H7	0.8146	0.6917	0.1629	0.041*
C8	0.6534 (2)	0.58600 (8)	0.15034 (10)	0.0282 (3)
C9	0.4756 (2)	0.61434 (9)	0.09111 (10)	0.0338 (3)
H9	0.4694	0.6691	0.0736	0.041*
C10	0.3145 (2)	0.56566 (10)	0.05886 (10)	0.0346 (3)
H10	0.1974	0.5847	0.0185	0.042*
C11	0.3302 (2)	0.48621 (9)	0.08821 (10)	0.0289 (3)
C12	0.2541 (2)	0.35928 (9)	0.10221 (10)	0.0309 (3)
C13	0.1180 (3)	0.28882 (10)	0.08024 (12)	0.0399 (4)
H13A	0.1879	0.2409	0.1079	0.060*
H13B	0.0887	0.2822	0.0125	0.060*
H13C	−0.0124	0.2967	0.1058	0.060*
C14	0.5188 (2)	0.33407 (8)	0.33886 (9)	0.0254 (3)
C15	0.6874 (2)	0.33510 (9)	0.40837 (11)	0.0330 (3)
H15	0.8197	0.3177	0.3958	0.040*
C16	0.6611 (2)	0.36179 (10)	0.49654 (11)	0.0367 (3)
H16	0.7769	0.3626	0.5442	0.044*
C17	0.4692 (2)	0.38742 (9)	0.51671 (10)	0.0318 (3)
C18	0.3013 (2)	0.38436 (9)	0.44579 (10)	0.0316 (3)
H18	0.1685	0.4011	0.4585	0.038*
C19	0.3236 (2)	0.35751 (8)	0.35733 (10)	0.0289 (3)
H19	0.2072	0.3551	0.3100	0.035*
C20	0.4422 (3)	0.41837 (11)	0.61182 (11)	0.0416 (4)
H20A	0.5394	0.3909	0.6590	0.062*
H20B	0.2997	0.4084	0.6236	0.062*
H20C	0.4700	0.4759	0.6147	0.062*

	U11	U22	U33	U12	U13	U23
S1	0.0360 (2)	0.02007 (18)	0.0343 (2)	0.00179 (13)	0.00981 (14)	−0.00098 (13)
O1	0.0290 (5)	0.0398 (6)	0.0299 (5)	0.0007 (4)	0.0012 (4)	−0.0028 (4)
O2	0.0378 (6)	0.0329 (6)	0.0494 (7)	0.0121 (5)	0.0161 (5)	0.0032 (5)
C1	0.0293 (7)	0.0260 (7)	0.0259 (7)	−0.0002 (5)	0.0068 (5)	−0.0021 (5)
C2	0.0282 (6)	0.0246 (7)	0.0232 (6)	0.0036 (5)	0.0066 (5)	−0.0009 (5)
C3	0.0295 (7)	0.0231 (7)	0.0245 (6)	0.0023 (5)	0.0079 (5)	−0.0015 (5)
C4	0.0299 (7)	0.0235 (7)	0.0372 (8)	0.0009 (5)	0.0058 (6)	0.0014 (6)
C5	0.0304 (7)	0.0335 (8)	0.0458 (9)	−0.0007 (6)	0.0027 (6)	0.0006 (7)
C6	0.0354 (8)	0.0310 (8)	0.0475 (9)	−0.0082 (6)	0.0110 (7)	−0.0053 (7)
C7	0.0440 (8)	0.0223 (7)	0.0384 (8)	−0.0018 (6)	0.0158 (7)	−0.0008 (6)
C8	0.0362 (7)	0.0237 (7)	0.0265 (7)	0.0023 (5)	0.0114 (6)	−0.0009 (5)
C9	0.0449 (8)	0.0266 (7)	0.0312 (7)	0.0101 (6)	0.0101 (6)	0.0046 (6)
C10	0.0372 (8)	0.0365 (8)	0.0295 (7)	0.0117 (6)	0.0023 (6)	0.0039 (6)
C11	0.0285 (7)	0.0326 (7)	0.0259 (7)	0.0027 (6)	0.0049 (5)	−0.0023 (6)
C12	0.0322 (7)	0.0336 (8)	0.0281 (7)	−0.0011 (6)	0.0086 (6)	−0.0044 (6)
C13	0.0371 (8)	0.0427 (9)	0.0402 (9)	−0.0106 (7)	0.0061 (7)	−0.0088 (7)
C14	0.0293 (7)	0.0188 (6)	0.0285 (7)	0.0001 (5)	0.0054 (5)	0.0029 (5)
C15	0.0266 (7)	0.0340 (8)	0.0383 (8)	0.0012 (6)	0.0041 (6)	0.0032 (6)
C16	0.0325 (7)	0.0423 (9)	0.0338 (8)	−0.0025 (6)	−0.0016 (6)	0.0031 (7)
C17	0.0374 (8)	0.0288 (7)	0.0299 (7)	−0.0075 (6)	0.0070 (6)	0.0017 (6)
C18	0.0291 (7)	0.0315 (8)	0.0354 (8)	0.0003 (6)	0.0090 (6)	0.0010 (6)
C19	0.0267 (7)	0.0285 (7)	0.0311 (7)	0.0007 (5)	0.0029 (5)	0.0020 (6)
C20	0.0502 (9)	0.0444 (9)	0.0318 (8)	−0.0107 (8)	0.0111 (7)	−0.0035 (7)

S1—O2	1.4938 (11)	C9—H9	0.9500
S1—C1	1.7573 (15)	C10—C11	1.396 (2)
S1—C14	1.7964 (14)	C10—H10	0.9500
O1—C12	1.3662 (18)	C12—C13	1.483 (2)
O1—C11	1.3727 (17)	C13—H13A	0.9800
C1—C12	1.360 (2)	C13—H13B	0.9800
C1—C2	1.4537 (19)	C13—H13C	0.9800
C2—C11	1.3813 (19)	C14—C15	1.384 (2)
C2—C3	1.4232 (19)	C14—C19	1.3901 (18)
C3—C4	1.413 (2)	C15—C16	1.386 (2)
C3—C8	1.4293 (19)	C15—H15	0.9500
C4—C5	1.371 (2)	C16—C17	1.389 (2)
C4—H4	0.9500	C16—H16	0.9500
C5—C6	1.406 (2)	C17—C18	1.394 (2)
C5—H5	0.9500	C17—C20	1.505 (2)
C6—C7	1.359 (2)	C18—C19	1.385 (2)
C6—H6	0.9500	C18—H18	0.9500
C7—C8	1.414 (2)	C19—H19	0.9500
C7—H7	0.9500	C20—H20A	0.9800
C8—C9	1.424 (2)	C20—H20B	0.9800
C9—C10	1.359 (2)	C20—H20C	0.9800
O2—S1—C1	111.27 (6)	O1—C11—C10	123.78 (13)
O2—S1—C14	106.16 (7)	C2—C11—C10	124.97 (14)
C1—S1—C14	98.40 (6)	C1—C12—O1	110.52 (13)
C12—O1—C11	106.72 (11)	C1—C12—C13	134.00 (15)
C12—C1—C2	107.26 (13)	O1—C12—C13	115.48 (13)
C12—C1—S1	119.03 (11)	C12—C13—H13A	109.5
C2—C1—S1	133.49 (11)	C12—C13—H13B	109.5
C11—C2—C3	118.98 (13)	H13A—C13—H13B	109.5
C11—C2—C1	104.24 (12)	C12—C13—H13C	109.5
C3—C2—C1	136.67 (13)	H13A—C13—H13C	109.5
C4—C3—C2	124.22 (13)	H13B—C13—H13C	109.5
C4—C3—C8	118.95 (13)	C15—C14—C19	120.66 (13)
C2—C3—C8	116.82 (13)	C15—C14—S1	119.20 (10)
C5—C4—C3	120.60 (14)	C19—C14—S1	119.84 (11)
C5—C4—H4	119.7	C14—C15—C16	119.32 (13)
C3—C4—H4	119.7	C14—C15—H15	120.3
C4—C5—C6	120.57 (15)	C16—C15—H15	120.3
C4—C5—H5	119.7	C15—C16—C17	121.45 (14)
C6—C5—H5	119.7	C15—C16—H16	119.3
C7—C6—C5	119.97 (14)	C17—C16—H16	119.3
C7—C6—H6	120.0	C16—C17—C18	117.99 (14)
C5—C6—H6	120.0	C16—C17—C20	121.35 (14)
C6—C7—C8	121.65 (14)	C18—C17—C20	120.66 (14)
C6—C7—H7	119.2	C19—C18—C17	121.58 (13)
C8—C7—H7	119.2	C19—C18—H18	119.2
C7—C8—C9	121.24 (13)	C17—C18—H18	119.2
C7—C8—C3	118.23 (13)	C18—C19—C14	118.97 (13)
C9—C8—C3	120.51 (13)	C18—C19—H19	120.5
C10—C9—C8	122.13 (14)	C14—C19—H19	120.5
C10—C9—H9	118.9	C17—C20—H20A	109.5
C8—C9—H9	118.9	C17—C20—H20B	109.5
C9—C10—C11	116.49 (14)	H20A—C20—H20B	109.5
C9—C10—H10	121.8	C17—C20—H20C	109.5
C11—C10—H10	121.8	H20A—C20—H20C	109.5
O1—C11—C2	111.24 (12)	H20B—C20—H20C	109.5
O2—S1—C1—C12	137.65 (11)	C12—O1—C11—C10	179.24 (13)
C14—S1—C1—C12	−111.29 (12)	C3—C2—C11—O1	176.11 (11)
O2—S1—C1—C2	−48.61 (15)	C1—C2—C11—O1	−0.85 (14)
C14—S1—C1—C2	62.45 (14)	C3—C2—C11—C10	−3.1 (2)
C12—C1—C2—C11	1.38 (14)	C1—C2—C11—C10	179.93 (13)
S1—C1—C2—C11	−172.89 (11)	C9—C10—C11—O1	−178.33 (13)
C12—C1—C2—C3	−174.74 (15)	C9—C10—C11—C2	0.8 (2)
S1—C1—C2—C3	11.0 (2)	C2—C1—C12—O1	−1.46 (15)
C11—C2—C3—C4	−175.09 (12)	S1—C1—C12—O1	173.79 (9)
C1—C2—C3—C4	0.6 (2)	C2—C1—C12—C13	179.00 (15)
C11—C2—C3—C8	3.32 (18)	S1—C1—C12—C13	−5.8 (2)
C1—C2—C3—C8	179.02 (14)	C11—O1—C12—C1	0.93 (15)
C2—C3—C4—C5	179.31 (13)	C11—O1—C12—C13	−179.43 (12)
C8—C3—C4—C5	0.9 (2)	O2—S1—C14—C15	−15.36 (13)
C3—C4—C5—C6	0.6 (2)	C1—S1—C14—C15	−130.48 (12)
C4—C5—C6—C7	−1.4 (2)	O2—S1—C14—C19	170.95 (11)
C5—C6—C7—C8	0.6 (2)	C1—S1—C14—C19	55.83 (12)
C6—C7—C8—C9	−177.67 (14)	C19—C14—C15—C16	−1.7 (2)
C6—C7—C8—C3	1.0 (2)	S1—C14—C15—C16	−175.29 (12)
C4—C3—C8—C7	−1.69 (19)	C14—C15—C16—C17	0.1 (2)
C2—C3—C8—C7	179.81 (12)	C15—C16—C17—C18	1.0 (2)
C4—C3—C8—C9	176.95 (12)	C15—C16—C17—C20	−178.40 (15)
C2—C3—C8—C9	−1.56 (18)	C16—C17—C18—C19	−0.7 (2)
C7—C8—C9—C10	177.87 (14)	C20—C17—C18—C19	178.78 (14)
C3—C8—C9—C10	−0.7 (2)	C17—C18—C19—C14	−0.8 (2)
C8—C9—C10—C11	1.2 (2)	C15—C14—C19—C18	2.0 (2)
C12—O1—C11—C2	0.01 (15)	S1—C14—C19—C18	175.61 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2i	0.95	2.48	3.3211 (19)	147.
C10—H10···O1ii	0.95	2.59	3.4579 (19)	152.
C13—H13C···O2iii	0.98	2.35	3.2538 (19)	153.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2i	0.95	2.48	3.3211 (19)	147
C10—H10⋯O1ii	0.95	2.59	3.4579 (19)	152
C13—H13C⋯O2iii	0.98	2.35	3.2538 (19)	153

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