2-Methyl-1-(3-methyl-phenyl-sulfon-yl)naphtho-[2,1-b]furan.

In the title compound, C20H16O3S, the dihedral angle between the mean planes of the naphtho-furan and 3-methyl-phenyl fragments is 88.56 (2)°. In the crystal, mol-ecules are linked via pairs of C-H⋯O hydrogen bonds, forming inversion dimers. These dimers are linked by π-π inter-actions between the furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.701 (2) Å] into supra-molecular chains running along the a-axis direction.

Related literature

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

Experimental

Crystal data

C20H16O3S

M = 336.39

Monoclinic,

a = 11.1667 (2) Å

b = 7.7400 (1) Å

c = 18.4736 (3) Å

β = 98.683 (1)°

V = 1578.38 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 173 K

0.51 × 0.25 × 0.21 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.697, T max = 0.746

15253 measured reflections

3946 independent reflections

3390 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.117

S = 1.05

3946 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.52 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 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/S1600536814005157/zq2218sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814005157/zq2218Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814005157/zq2218Isup3.cml

CCDC reference: 990319

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

C20H16O3S	F(000) = 704
Mr = 336.39	Dx = 1.416 Mg m−3
Monoclinic, P21/n	Melting point = 424–425 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 11.1667 (2) Å	Cell parameters from 5868 reflections
b = 7.7400 (1) Å	θ = 2.2–28.3°
c = 18.4736 (3) Å	µ = 0.22 mm−1
β = 98.683 (1)°	T = 173 K
V = 1578.38 (4) Å3	Block, colourless
Z = 4	0.51 × 0.25 × 0.21 mm

Bruker SMART APEXII CCD diffractometer	3946 independent reflections
Radiation source: rotating anode	3390 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.026
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 2.0°
φ and ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −8→10
Tmin = 0.697, Tmax = 0.746	l = −24→18
15253 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)] = 0.042	Hydrogen site location: difference Fourier map
wR(F2) = 0.117	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0606P)2 + 0.6579P] where P = (Fo2 + 2Fc2)/3
3946 reflections	(Δ/σ)max = 0.003
219 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.52 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	0.28214 (3)	0.08312 (5)	0.611416 (19)	0.02882 (12)
O1	−0.04251 (10)	0.26951 (15)	0.55227 (6)	0.0352 (3)
O2	0.33118 (11)	−0.05146 (14)	0.57127 (6)	0.0358 (3)
O3	0.26812 (12)	0.04900 (17)	0.68617 (6)	0.0421 (3)
C1	0.14243 (13)	0.1526 (2)	0.56462 (8)	0.0277 (3)
C2	0.10413 (13)	0.18600 (18)	0.48678 (8)	0.0262 (3)
C3	0.14969 (13)	0.16201 (19)	0.41891 (8)	0.0265 (3)
C4	0.26063 (14)	0.0823 (2)	0.41147 (8)	0.0314 (3)
H4	0.3118	0.0418	0.4538	0.038*
C5	0.29601 (17)	0.0623 (2)	0.34395 (9)	0.0385 (4)
H5	0.3706	0.0065	0.3401	0.046*
C6	0.22342 (17)	0.1234 (3)	0.28055 (9)	0.0416 (4)
H6	0.2493	0.1107	0.2342	0.050*
C7	0.11597 (16)	0.2006 (2)	0.28576 (9)	0.0393 (4)
H7	0.0673	0.2417	0.2425	0.047*
C8	0.07448 (14)	0.2216 (2)	0.35393 (8)	0.0311 (3)
C9	−0.04140 (15)	0.2957 (2)	0.35690 (9)	0.0375 (4)
H9	−0.0893	0.3333	0.3128	0.045*
C10	−0.08502 (14)	0.3139 (2)	0.42102 (10)	0.0368 (4)
H10	−0.1627	0.3620	0.4231	0.044*
C11	−0.00957 (14)	0.2578 (2)	0.48414 (8)	0.0303 (3)
C12	0.05076 (14)	0.2062 (2)	0.60067 (9)	0.0331 (3)
C13	0.02986 (18)	0.2145 (3)	0.67799 (10)	0.0458 (4)
H13A	0.0765	0.3104	0.7028	0.069*
H13B	0.0558	0.1058	0.7027	0.069*
H13C	−0.0566	0.2327	0.6795	0.069*
C14	0.37544 (13)	0.26733 (19)	0.61112 (7)	0.0259 (3)
C15	0.48014 (13)	0.25965 (19)	0.57933 (8)	0.0272 (3)
H15	0.4995	0.1573	0.5552	0.033*
C16	0.55711 (14)	0.4026 (2)	0.58282 (8)	0.0298 (3)
C17	0.52185 (16)	0.5523 (2)	0.61525 (9)	0.0343 (3)
H17	0.5717	0.6520	0.6165	0.041*
C18	0.41605 (16)	0.5603 (2)	0.64579 (8)	0.0332 (3)
H18	0.3937	0.6652	0.6669	0.040*
C19	0.34312 (14)	0.4162 (2)	0.64559 (8)	0.0301 (3)
H19	0.2725	0.4187	0.6685	0.036*
C20	0.67508 (15)	0.3947 (2)	0.55323 (10)	0.0399 (4)
H20A	0.6927	0.5080	0.5337	0.060*
H20B	0.6693	0.3083	0.5141	0.060*
H20C	0.7402	0.3625	0.5926	0.060*

	U11	U22	U33	U12	U13	U23
S1	0.0321 (2)	0.0276 (2)	0.02405 (19)	−0.00269 (14)	−0.00458 (14)	0.00574 (13)
O1	0.0277 (5)	0.0399 (6)	0.0380 (6)	−0.0019 (4)	0.0049 (5)	0.0031 (5)
O2	0.0397 (6)	0.0253 (5)	0.0383 (6)	0.0018 (4)	−0.0070 (5)	0.0009 (4)
O3	0.0486 (7)	0.0488 (7)	0.0261 (6)	−0.0086 (6)	−0.0036 (5)	0.0138 (5)
C1	0.0278 (7)	0.0292 (7)	0.0249 (7)	−0.0043 (6)	−0.0001 (5)	0.0041 (6)
C2	0.0250 (6)	0.0254 (7)	0.0259 (7)	−0.0049 (5)	−0.0031 (5)	0.0038 (5)
C3	0.0284 (7)	0.0249 (7)	0.0239 (7)	−0.0065 (5)	−0.0027 (5)	0.0027 (5)
C4	0.0324 (8)	0.0325 (8)	0.0276 (7)	−0.0017 (6)	−0.0010 (6)	0.0009 (6)
C5	0.0406 (9)	0.0416 (9)	0.0331 (8)	−0.0031 (7)	0.0052 (7)	−0.0044 (7)
C6	0.0490 (10)	0.0495 (10)	0.0261 (7)	−0.0123 (8)	0.0052 (7)	−0.0019 (7)
C7	0.0470 (10)	0.0426 (9)	0.0246 (7)	−0.0124 (8)	−0.0062 (7)	0.0061 (7)
C8	0.0340 (8)	0.0290 (7)	0.0273 (7)	−0.0086 (6)	−0.0051 (6)	0.0059 (6)
C9	0.0342 (8)	0.0375 (9)	0.0357 (8)	−0.0032 (7)	−0.0114 (6)	0.0107 (7)
C10	0.0270 (7)	0.0365 (9)	0.0436 (9)	−0.0005 (6)	−0.0056 (6)	0.0077 (7)
C11	0.0269 (7)	0.0299 (8)	0.0330 (8)	−0.0045 (6)	0.0013 (6)	0.0035 (6)
C12	0.0318 (8)	0.0357 (8)	0.0313 (8)	−0.0069 (6)	0.0030 (6)	0.0040 (6)
C13	0.0469 (10)	0.0577 (12)	0.0353 (9)	−0.0073 (9)	0.0140 (8)	0.0013 (8)
C14	0.0278 (7)	0.0264 (7)	0.0210 (6)	0.0002 (5)	−0.0038 (5)	0.0018 (5)
C15	0.0304 (7)	0.0265 (7)	0.0230 (6)	0.0022 (6)	−0.0019 (5)	−0.0009 (5)
C16	0.0307 (7)	0.0331 (8)	0.0239 (7)	−0.0017 (6)	−0.0013 (6)	0.0030 (6)
C17	0.0408 (9)	0.0293 (8)	0.0304 (7)	−0.0062 (6)	−0.0021 (6)	0.0008 (6)
C18	0.0418 (9)	0.0277 (8)	0.0277 (7)	0.0031 (6)	−0.0021 (6)	−0.0039 (6)
C19	0.0313 (7)	0.0333 (8)	0.0244 (7)	0.0044 (6)	0.0000 (6)	0.0000 (6)
C20	0.0347 (8)	0.0470 (10)	0.0383 (9)	−0.0043 (7)	0.0067 (7)	0.0022 (7)

S1—O2	1.4344 (12)	C9—H9	0.9500
S1—O3	1.4375 (12)	C10—C11	1.400 (2)
S1—C1	1.7504 (15)	C10—H10	0.9500
S1—C14	1.7664 (15)	C12—C13	1.483 (2)
O1—C12	1.3577 (19)	C13—H13A	0.9800
O1—C11	1.3665 (19)	C13—H13B	0.9800
C1—C12	1.367 (2)	C13—H13C	0.9800
C1—C2	1.4600 (19)	C14—C15	1.387 (2)
C2—C11	1.380 (2)	C14—C19	1.391 (2)
C2—C3	1.435 (2)	C15—C16	1.397 (2)
C3—C4	1.409 (2)	C15—H15	0.9500
C3—C8	1.4334 (19)	C16—C17	1.388 (2)
C4—C5	1.373 (2)	C16—C20	1.502 (2)
C4—H4	0.9500	C17—C18	1.385 (2)
C5—C6	1.402 (2)	C17—H17	0.9500
C5—H5	0.9500	C18—C19	1.381 (2)
C6—C7	1.357 (3)	C18—H18	0.9500
C6—H6	0.9500	C19—H19	0.9500
C7—C8	1.415 (2)	C20—H20A	0.9800
C7—H7	0.9500	C20—H20B	0.9800
C8—C9	1.424 (2)	C20—H20C	0.9800
C9—C10	1.354 (2)
O2—S1—O3	117.96 (8)	O1—C11—C2	111.60 (13)
O2—S1—C1	110.44 (7)	O1—C11—C10	122.32 (14)
O3—S1—C1	108.22 (7)	C2—C11—C10	126.08 (15)
O2—S1—C14	108.25 (7)	O1—C12—C1	110.18 (13)
O3—S1—C14	107.53 (7)	O1—C12—C13	113.71 (14)
C1—S1—C14	103.44 (7)	C1—C12—C13	136.10 (15)
C12—O1—C11	107.24 (12)	C12—C13—H13A	109.5
C12—C1—C2	107.26 (13)	C12—C13—H13B	109.5
C12—C1—S1	121.98 (12)	H13A—C13—H13B	109.5
C2—C1—S1	130.36 (12)	C12—C13—H13C	109.5
C11—C2—C3	117.84 (13)	H13A—C13—H13C	109.5
C11—C2—C1	103.73 (13)	H13B—C13—H13C	109.5
C3—C2—C1	138.43 (14)	C15—C14—C19	121.55 (14)
C4—C3—C8	118.15 (14)	C15—C14—S1	120.14 (11)
C4—C3—C2	125.10 (13)	C19—C14—S1	118.26 (12)
C8—C3—C2	116.74 (14)	C14—C15—C16	119.92 (14)
C5—C4—C3	121.06 (15)	C14—C15—H15	120.0
C5—C4—H4	119.5	C16—C15—H15	120.0
C3—C4—H4	119.5	C17—C16—C15	117.93 (14)
C4—C5—C6	120.78 (17)	C17—C16—C20	120.87 (15)
C4—C5—H5	119.6	C15—C16—C20	121.20 (15)
C6—C5—H5	119.6	C18—C17—C16	121.89 (15)
C7—C6—C5	119.68 (16)	C18—C17—H17	119.1
C7—C6—H6	120.2	C16—C17—H17	119.1
C5—C6—H6	120.2	C19—C18—C17	120.11 (15)
C6—C7—C8	121.69 (15)	C19—C18—H18	119.9
C6—C7—H7	119.2	C17—C18—H18	119.9
C8—C7—H7	119.2	C18—C19—C14	118.48 (14)
C7—C8—C9	120.12 (14)	C18—C19—H19	120.8
C7—C8—C3	118.63 (15)	C14—C19—H19	120.8
C9—C8—C3	121.22 (15)	C16—C20—H20A	109.5
C10—C9—C8	121.62 (14)	C16—C20—H20B	109.5
C10—C9—H9	119.2	H20A—C20—H20B	109.5
C8—C9—H9	119.2	C16—C20—H20C	109.5
C9—C10—C11	116.46 (15)	H20A—C20—H20C	109.5
C9—C10—H10	121.8	H20B—C20—H20C	109.5
C11—C10—H10	121.8
O2—S1—C1—C12	146.07 (13)	C12—O1—C11—C10	−179.39 (15)
O3—S1—C1—C12	15.58 (16)	C3—C2—C11—O1	178.61 (12)
C14—S1—C1—C12	−98.29 (14)	C1—C2—C11—O1	−0.30 (16)
O2—S1—C1—C2	−42.19 (16)	C3—C2—C11—C10	−1.4 (2)
O3—S1—C1—C2	−172.68 (14)	C1—C2—C11—C10	179.63 (15)
C14—S1—C1—C2	73.45 (15)	C9—C10—C11—O1	179.74 (14)
C12—C1—C2—C11	−0.05 (17)	C9—C10—C11—C2	−0.2 (2)
S1—C1—C2—C11	−172.72 (12)	C11—O1—C12—C1	−0.58 (17)
C12—C1—C2—C3	−178.61 (17)	C11—O1—C12—C13	178.46 (14)
S1—C1—C2—C3	8.7 (3)	C2—C1—C12—O1	0.39 (18)
C11—C2—C3—C4	−176.38 (14)	S1—C1—C12—O1	173.81 (10)
C1—C2—C3—C4	2.0 (3)	C2—C1—C12—C13	−178.34 (19)
C11—C2—C3—C8	2.4 (2)	S1—C1—C12—C13	−4.9 (3)
C1—C2—C3—C8	−179.15 (16)	O2—S1—C14—C15	−3.80 (13)
C8—C3—C4—C5	0.1 (2)	O3—S1—C14—C15	124.65 (12)
C2—C3—C4—C5	178.88 (14)	C1—S1—C14—C15	−120.98 (12)
C3—C4—C5—C6	1.0 (3)	O2—S1—C14—C19	178.42 (11)
C4—C5—C6—C7	−1.1 (3)	O3—S1—C14—C19	−53.14 (13)
C5—C6—C7—C8	−0.1 (3)	C1—S1—C14—C19	61.23 (12)
C6—C7—C8—C9	−176.92 (16)	C19—C14—C15—C16	1.3 (2)
C6—C7—C8—C3	1.1 (2)	S1—C14—C15—C16	−176.43 (10)
C4—C3—C8—C7	−1.1 (2)	C14—C15—C16—C17	−3.3 (2)
C2—C3—C8—C7	179.96 (13)	C14—C15—C16—C20	176.02 (14)
C4—C3—C8—C9	176.90 (14)	C15—C16—C17—C18	2.2 (2)
C2—C3—C8—C9	−2.0 (2)	C20—C16—C17—C18	−177.12 (15)
C7—C8—C9—C10	178.41 (15)	C16—C17—C18—C19	1.0 (2)
C3—C8—C9—C10	0.4 (2)	C17—C18—C19—C14	−3.1 (2)
C8—C9—C10—C11	0.7 (2)	C15—C14—C19—C18	2.0 (2)
C12—O1—C11—C2	0.55 (17)	S1—C14—C19—C18	179.72 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20B···O2i	0.98	2.54	3.507 (2)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20B⋯O2i	0.98	2.54	3.507 (2)	171

Symmetry code: (i) .