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

In the title compound, C(20)H(16)O(3)S, the 4-methyl-phenyl ring makes a dihedral angle of 83.07 (3)° with the mean plane [r.m.s. deviation = 0.020 (1) Å] of the naphtho-furan fragment. In the crystal, mol-ecules are linked by weak C-H⋯O and C-H⋯π inter-actions.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2008 ▶, 2012 ▶).

Experimental

Crystal data

C20H16O3S

M = 336.39

Monoclinic,

a = 8.6628 (2) Å

b = 6.3669 (1) Å

c = 28.9119 (6) Å

β = 96.795 (1)°

V = 1583.44 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 173 K

0.35 × 0.32 × 0.28 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.676, T max = 0.746

14714 measured reflections

3958 independent reflections

3363 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.113

S = 1.04

3958 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.32 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 datablock(s) global, I. DOI: 10.1107/S1600536812012159/hb6696sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012159/hb6696Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812012159/hb6696Isup3.cml

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

C20H16O3S	F(000) = 704
Mr = 336.39	Dx = 1.411 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5369 reflections
a = 8.6628 (2) Å	θ = 2.4–28.2°
b = 6.3669 (1) Å	µ = 0.22 mm−1
c = 28.9119 (6) Å	T = 173 K
β = 96.795 (1)°	Block, colourless
V = 1583.44 (6) Å3	0.35 × 0.32 × 0.28 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3958 independent reflections
Radiation source: rotating anode	3363 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.029
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 1.4°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −8→8
Tmin = 0.676, Tmax = 0.746	l = −38→36
14714 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) = 0.113	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0592P)2 + 0.6896P] where P = (Fo2 + 2Fc2)/3
3958 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.32 e Å−3
0 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
S1	0.27965 (4)	0.47230 (6)	0.122492 (12)	0.02209 (11)
O1	0.53486 (13)	0.23737 (18)	0.03339 (4)	0.0289 (3)
O2	0.14170 (12)	0.35873 (19)	0.10517 (4)	0.0307 (3)
O3	0.26753 (12)	0.69453 (18)	0.12988 (4)	0.0298 (3)
C1	0.41907 (16)	0.4236 (2)	0.08492 (5)	0.0219 (3)
C2	0.56531 (16)	0.5295 (2)	0.07891 (5)	0.0213 (3)
C3	0.65037 (16)	0.7128 (2)	0.09593 (5)	0.0218 (3)
C4	0.60027 (17)	0.8614 (2)	0.12726 (5)	0.0247 (3)
H4	0.5033	0.8415	0.1389	0.030*
C5	0.68864 (19)	1.0335 (3)	0.14119 (6)	0.0295 (3)
H5	0.6519	1.1313	0.1622	0.035*
C6	0.83300 (19)	1.0672 (3)	0.12478 (6)	0.0332 (4)
H6	0.8936	1.1870	0.1345	0.040*
C7	0.88506 (18)	0.9260 (3)	0.09476 (6)	0.0316 (4)
H7	0.9831	0.9485	0.0840	0.038*
C8	0.79719 (16)	0.7470 (2)	0.07925 (5)	0.0254 (3)
C9	0.85486 (18)	0.6061 (3)	0.04712 (6)	0.0305 (3)
H9	0.9540	0.6316	0.0373	0.037*
C10	0.77213 (19)	0.4364 (3)	0.03018 (6)	0.0308 (3)
H10	0.8093	0.3442	0.0082	0.037*
C11	0.62874 (18)	0.4049 (2)	0.04693 (5)	0.0251 (3)
C12	0.40872 (18)	0.2496 (2)	0.05693 (5)	0.0260 (3)
C13	0.2966 (2)	0.0750 (3)	0.04686 (6)	0.0349 (4)
H13A	0.3285	−0.0119	0.0217	0.052*
H13B	0.1927	0.1325	0.0374	0.052*
H13C	0.2943	−0.0110	0.0749	0.052*
C14	0.35605 (16)	0.3550 (2)	0.17546 (5)	0.0218 (3)
C15	0.46746 (18)	0.4594 (3)	0.20557 (5)	0.0279 (3)
H15	0.4992	0.5975	0.1985	0.033*
C16	0.53175 (19)	0.3600 (3)	0.24596 (5)	0.0320 (4)
H16	0.6078	0.4310	0.2666	0.038*
C17	0.48649 (18)	0.1574 (3)	0.25668 (5)	0.0298 (3)
C18	0.37223 (19)	0.0579 (3)	0.22656 (6)	0.0291 (3)
H18	0.3380	−0.0784	0.2340	0.035*
C19	0.30745 (17)	0.1542 (2)	0.18583 (5)	0.0253 (3)
H19	0.2308	0.0838	0.1652	0.030*
C20	0.5594 (2)	0.0488 (3)	0.30016 (6)	0.0441 (5)
H20A	0.5242	0.1161	0.3275	0.066*
H20B	0.6729	0.0591	0.3020	0.066*
H20C	0.5287	−0.0994	0.2992	0.066*

	U11	U22	U33	U12	U13	U23
S1	0.01901 (17)	0.0225 (2)	0.02499 (19)	−0.00027 (13)	0.00374 (13)	0.00294 (13)
O1	0.0367 (6)	0.0263 (6)	0.0254 (5)	−0.0045 (5)	0.0102 (4)	−0.0036 (4)
O2	0.0212 (5)	0.0360 (7)	0.0345 (6)	−0.0048 (5)	0.0009 (4)	0.0022 (5)
O3	0.0270 (5)	0.0233 (6)	0.0403 (6)	0.0038 (4)	0.0093 (5)	0.0044 (5)
C1	0.0227 (6)	0.0237 (7)	0.0195 (6)	−0.0006 (5)	0.0028 (5)	0.0026 (5)
C2	0.0217 (6)	0.0232 (7)	0.0193 (6)	0.0012 (5)	0.0031 (5)	0.0034 (5)
C3	0.0210 (6)	0.0231 (7)	0.0210 (6)	0.0007 (5)	0.0014 (5)	0.0047 (5)
C4	0.0240 (7)	0.0236 (7)	0.0266 (7)	0.0005 (6)	0.0037 (5)	0.0011 (6)
C5	0.0308 (8)	0.0261 (8)	0.0313 (8)	−0.0006 (6)	0.0030 (6)	−0.0022 (6)
C6	0.0299 (8)	0.0312 (9)	0.0375 (9)	−0.0099 (7)	0.0004 (6)	−0.0011 (7)
C7	0.0241 (7)	0.0358 (9)	0.0352 (8)	−0.0076 (6)	0.0048 (6)	0.0033 (7)
C8	0.0220 (6)	0.0291 (8)	0.0249 (7)	−0.0004 (6)	0.0026 (5)	0.0041 (6)
C9	0.0257 (7)	0.0366 (9)	0.0309 (8)	0.0011 (7)	0.0108 (6)	0.0043 (7)
C10	0.0331 (8)	0.0327 (9)	0.0286 (8)	0.0022 (7)	0.0124 (6)	0.0000 (6)
C11	0.0301 (7)	0.0234 (7)	0.0225 (7)	−0.0016 (6)	0.0056 (6)	0.0014 (6)
C12	0.0316 (7)	0.0256 (8)	0.0210 (7)	−0.0037 (6)	0.0042 (5)	0.0015 (6)
C13	0.0430 (9)	0.0297 (9)	0.0326 (8)	−0.0117 (7)	0.0066 (7)	−0.0041 (7)
C14	0.0233 (6)	0.0215 (7)	0.0216 (6)	0.0020 (5)	0.0061 (5)	0.0003 (5)
C15	0.0312 (7)	0.0259 (8)	0.0268 (7)	−0.0050 (6)	0.0048 (6)	−0.0002 (6)
C16	0.0334 (8)	0.0370 (9)	0.0250 (7)	−0.0034 (7)	0.0007 (6)	−0.0018 (7)
C17	0.0316 (8)	0.0362 (9)	0.0227 (7)	0.0050 (7)	0.0080 (6)	0.0045 (6)
C18	0.0339 (8)	0.0253 (8)	0.0297 (8)	0.0003 (6)	0.0097 (6)	0.0033 (6)
C19	0.0274 (7)	0.0231 (7)	0.0262 (7)	−0.0024 (6)	0.0069 (6)	0.0000 (6)
C20	0.0469 (10)	0.0543 (12)	0.0306 (9)	0.0023 (9)	0.0021 (8)	0.0138 (8)

S1—O2	1.4354 (11)	C9—H9	0.9500
S1—O3	1.4366 (12)	C10—C11	1.400 (2)
S1—C1	1.7450 (15)	C10—H10	0.9500
S1—C14	1.7611 (15)	C12—C13	1.483 (2)
O1—C12	1.3562 (18)	C13—H13A	0.9800
O1—C11	1.3700 (18)	C13—H13B	0.9800
C1—C12	1.369 (2)	C13—H13C	0.9800
C1—C2	1.4632 (19)	C14—C19	1.390 (2)
C2—C11	1.381 (2)	C14—C15	1.390 (2)
C2—C3	1.436 (2)	C15—C16	1.386 (2)
C3—C4	1.413 (2)	C15—H15	0.9500
C3—C8	1.4293 (19)	C16—C17	1.394 (2)
C4—C5	1.370 (2)	C16—H16	0.9500
C4—H4	0.9500	C17—C18	1.391 (2)
C5—C6	1.405 (2)	C17—C20	1.506 (2)
C5—H5	0.9500	C18—C19	1.386 (2)
C6—C7	1.363 (2)	C18—H18	0.9500
C6—H6	0.9500	C19—H19	0.9500
C7—C8	1.414 (2)	C20—H20A	0.9800
C7—H7	0.9500	C20—H20B	0.9800
C8—C9	1.424 (2)	C20—H20C	0.9800
C9—C10	1.355 (2)
O2—S1—O3	118.39 (7)	O1—C11—C2	111.64 (13)
O2—S1—C1	107.60 (7)	O1—C11—C10	122.26 (14)
O3—S1—C1	109.60 (7)	C2—C11—C10	126.08 (15)
O2—S1—C14	107.55 (7)	O1—C12—C1	110.07 (13)
O3—S1—C14	108.36 (7)	O1—C12—C13	113.98 (13)
C1—S1—C14	104.45 (7)	C1—C12—C13	135.95 (15)
C12—O1—C11	107.34 (11)	C12—C13—H13A	109.5
C12—C1—C2	107.44 (13)	C12—C13—H13B	109.5
C12—C1—S1	120.67 (11)	H13A—C13—H13B	109.5
C2—C1—S1	131.67 (11)	C12—C13—H13C	109.5
C11—C2—C3	117.89 (13)	H13A—C13—H13C	109.5
C11—C2—C1	103.51 (13)	H13B—C13—H13C	109.5
C3—C2—C1	138.60 (13)	C19—C14—C15	120.70 (14)
C4—C3—C8	117.86 (13)	C19—C14—S1	119.04 (11)
C4—C3—C2	125.43 (13)	C15—C14—S1	120.22 (12)
C8—C3—C2	116.70 (13)	C16—C15—C14	119.28 (15)
C5—C4—C3	121.38 (14)	C16—C15—H15	120.4
C5—C4—H4	119.3	C14—C15—H15	120.4
C3—C4—H4	119.3	C15—C16—C17	120.97 (15)
C4—C5—C6	120.75 (15)	C15—C16—H16	119.5
C4—C5—H5	119.6	C17—C16—H16	119.5
C6—C5—H5	119.6	C18—C17—C16	118.70 (14)
C7—C6—C5	119.30 (15)	C18—C17—C20	120.71 (16)
C7—C6—H6	120.4	C16—C17—C20	120.59 (16)
C5—C6—H6	120.4	C19—C18—C17	121.13 (15)
C6—C7—C8	121.82 (15)	C19—C18—H18	119.4
C6—C7—H7	119.1	C17—C18—H18	119.4
C8—C7—H7	119.1	C18—C19—C14	119.19 (14)
C7—C8—C9	119.84 (14)	C18—C19—H19	120.4
C7—C8—C3	118.89 (14)	C14—C19—H19	120.4
C9—C8—C3	121.26 (14)	C17—C20—H20A	109.5
C10—C9—C8	121.78 (14)	C17—C20—H20B	109.5
C10—C9—H9	119.1	H20A—C20—H20B	109.5
C8—C9—H9	119.1	C17—C20—H20C	109.5
C9—C10—C11	116.24 (15)	H20A—C20—H20C	109.5
C9—C10—H10	121.9	H20B—C20—H20C	109.5
C11—C10—H10	121.9
O2—S1—C1—C12	−21.68 (14)	C12—O1—C11—C10	178.08 (15)
O3—S1—C1—C12	−151.66 (12)	C3—C2—C11—O1	−179.34 (12)
C14—S1—C1—C12	92.43 (13)	C1—C2—C11—O1	0.22 (16)
O2—S1—C1—C2	164.56 (13)	C3—C2—C11—C10	2.0 (2)
O3—S1—C1—C2	34.58 (16)	C1—C2—C11—C10	−178.40 (15)
C14—S1—C1—C2	−81.34 (15)	C9—C10—C11—O1	−178.71 (15)
C12—C1—C2—C11	0.24 (16)	C9—C10—C11—C2	−0.2 (2)
S1—C1—C2—C11	174.62 (12)	C11—O1—C12—C1	0.76 (16)
C12—C1—C2—C3	179.65 (17)	C11—O1—C12—C13	−178.63 (13)
S1—C1—C2—C3	−6.0 (3)	C2—C1—C12—O1	−0.62 (17)
C11—C2—C3—C4	177.50 (14)	S1—C1—C12—O1	−175.75 (10)
C1—C2—C3—C4	−1.8 (3)	C2—C1—C12—C13	178.57 (17)
C11—C2—C3—C8	−2.0 (2)	S1—C1—C12—C13	3.4 (3)
C1—C2—C3—C8	178.65 (16)	O2—S1—C14—C19	17.39 (14)
C8—C3—C4—C5	0.3 (2)	O3—S1—C14—C19	146.47 (11)
C2—C3—C4—C5	−179.20 (14)	C1—S1—C14—C19	−96.75 (12)
C3—C4—C5—C6	−0.3 (2)	O2—S1—C14—C15	−164.89 (12)
C4—C5—C6—C7	−0.1 (3)	O3—S1—C14—C15	−35.81 (14)
C5—C6—C7—C8	0.6 (3)	C1—S1—C14—C15	80.97 (13)
C6—C7—C8—C9	178.71 (15)	C19—C14—C15—C16	0.9 (2)
C6—C7—C8—C3	−0.6 (2)	S1—C14—C15—C16	−176.78 (12)
C4—C3—C8—C7	0.1 (2)	C14—C15—C16—C17	0.1 (2)
C2—C3—C8—C7	179.66 (13)	C15—C16—C17—C18	−1.6 (2)
C4—C3—C8—C9	−179.15 (14)	C15—C16—C17—C20	178.72 (16)
C2—C3—C8—C9	0.4 (2)	C16—C17—C18—C19	2.1 (2)
C7—C8—C9—C10	−177.80 (16)	C20—C17—C18—C19	−178.24 (15)
C3—C8—C9—C10	1.5 (2)	C17—C18—C19—C14	−1.1 (2)
C8—C9—C10—C11	−1.5 (2)	C15—C14—C19—C18	−0.4 (2)
C12—O1—C11—C2	−0.60 (17)	S1—C14—C19—C18	177.28 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1i	0.98	2.54	3.503 (2)	168
C13—H13C···O3ii	0.98	2.49	3.440 (2)	164
C5—H5···Cgiii	0.95	2.80	3.648 (2)	149

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C14–C19 4-methyl­phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯O1i	0.98	2.54	3.503 (2)	168
C13—H13C⋯O3ii	0.98	2.49	3.440 (2)	164
C5—H5⋯Cgiii	0.95	2.80	3.648 (2)	149

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