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

The title compound, C(19)H(14)O(3)S, was prepared by the oxidation of 2-methyl-1-(phenyl-sulfan-yl)naphtho[2,1-b]furan with 3-chloro-peroxy-benzoic acid. The phenyl ring makes a dihedral angle of 87.13 (4)° with the plane of the naphthofuran fragment. The crystal structure is stabilized by π-π inter-actions between the furan and benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.850 (2) Å] and weak C-H⋯π inter-actions. In addition, there are also intra-molecular C-H⋯O inter-actions.

Related literature

For the crystal structures of similar 2-methyl­naphtho[2,1-b]furan compounds, see: Choi et al. (2006 ▶, 2007 ▶).

Experimental

Crystal data

C19H14O3S

M = 322.36

Monoclinic,

a = 10.7175 (4) Å

b = 7.7972 (3) Å

c = 18.0488 (7) Å

β = 97.797 (1)°

V = 1494.33 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 173 (2) K

0.40 × 0.40 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

8784 measured reflections

3222 independent reflections

2785 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.098

S = 1.05

3222 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.39 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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/S1600536808007046/fb2090sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007046/fb2090Isup2.hkl

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

C19H14O3S	F000 = 672
Mr = 322.36	Dx = 1.433 Mg m−3
Monoclinic, P21/n	Melting point = 431–432 K
Hall symbol: -P 2yn	Mo Kα radiation λ = 0.71073 Å
a = 10.7175 (4) Å	Cell parameters from 5468 reflections
b = 7.7972 (3) Å	θ = 2.3–28.2º
c = 18.0488 (7) Å	µ = 0.23 mm−1
β = 97.797 (1)º	T = 173 (2) K
V = 1494.33 (10) Å3	Block, colourless
Z = 4	0.40 × 0.40 × 0.20 mm

Bruker SMART CCD diffractometer	3222 independent reflections
Radiation source: fine-focus sealed tube	2785 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.023
Detector resolution: 10.0 pixels mm-1	θmax = 27.0º
T = 173(2) K	θmin = 2.9º
φ and ω scans	h = −13→11
Absorption correction: none	k = −9→9
8784 measured reflections	l = −23→23

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036	H-atom parameters constrained
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0464P)2 + 0.7406P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
3222 reflections	Δρmax = 0.33 e Å−3
210 parameters	Δρmin = −0.39 e Å−3
54 constraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (2)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
S	0.78568 (4)	0.07420 (5)	0.11326 (2)	0.02579 (13)
O1	0.44773 (10)	0.27156 (15)	0.07186 (6)	0.0317 (3)
O2	0.81955 (11)	−0.07018 (14)	0.07052 (7)	0.0327 (3)
O3	0.78345 (12)	0.05031 (17)	0.19220 (6)	0.0376 (3)
C1	0.63938 (14)	0.1558 (2)	0.07427 (8)	0.0251 (3)
C2	0.59348 (14)	0.19921 (19)	−0.00332 (8)	0.0239 (3)
C3	0.63656 (14)	0.18767 (19)	−0.07498 (8)	0.0246 (3)
C4	0.74995 (16)	0.1091 (2)	−0.08857 (9)	0.0294 (3)
H4	0.8031	0.0575	−0.0483	0.035*
C5	0.78480 (18)	0.1059 (2)	−0.15919 (9)	0.0360 (4)
H5	0.8612	0.0516	−0.1671	0.043*
C6	0.70826 (19)	0.1822 (3)	−0.21959 (9)	0.0407 (4)
H6	0.7339	0.1820	−0.2680	0.049*
C7	0.59747 (18)	0.2564 (2)	−0.20867 (9)	0.0383 (4)
H7	0.5460	0.3066	−0.2500	0.046*
C8	0.55669 (15)	0.2608 (2)	−0.13718 (9)	0.0297 (4)
C9	0.43790 (16)	0.3342 (2)	−0.12790 (10)	0.0355 (4)
H9	0.3867	0.3809	−0.1702	0.043*
C10	0.39621 (15)	0.3389 (2)	−0.06035 (10)	0.0335 (4)
H10	0.3164	0.3859	−0.0543	0.040*
C11	0.47661 (14)	0.2710 (2)	0.00014 (9)	0.0273 (3)
C12	0.54835 (15)	0.2028 (2)	0.11655 (9)	0.0294 (3)
C13	0.89432 (14)	0.24061 (19)	0.10214 (8)	0.0247 (3)
C14	0.87639 (16)	0.4045 (2)	0.12958 (9)	0.0299 (4)
H14	0.8035	0.4308	0.1520	0.036*
C15	0.96700 (17)	0.5283 (2)	0.12344 (9)	0.0351 (4)
H15	0.9550	0.6417	0.1403	0.042*
C16	1.07529 (17)	0.4877 (2)	0.09275 (9)	0.0367 (4)
H16	1.1377	0.5730	0.0897	0.044*
C17	1.09280 (16)	0.3244 (2)	0.06666 (10)	0.0360 (4)
H17	1.1675	0.2969	0.0463	0.043*
C18	1.00096 (15)	0.2003 (2)	0.07027 (9)	0.0301 (4)
H18	1.0112	0.0886	0.0510	0.036*
C19	0.53353 (18)	0.1975 (3)	0.19698 (10)	0.0414 (4)
H19A	0.4597	0.2651	0.2054	0.062*
H19B	0.6089	0.2455	0.2266	0.062*
H19C	0.5222	0.0784	0.2121	0.062*

	U11	U22	U33	U12	U13	U23
S	0.0269 (2)	0.0252 (2)	0.0241 (2)	0.00073 (15)	−0.00082 (14)	0.00240 (14)
O1	0.0246 (6)	0.0341 (6)	0.0373 (6)	−0.0007 (5)	0.0076 (5)	0.0014 (5)
O2	0.0342 (6)	0.0231 (6)	0.0394 (6)	0.0013 (5)	0.0005 (5)	−0.0007 (5)
O3	0.0411 (7)	0.0446 (7)	0.0259 (6)	−0.0008 (6)	−0.0007 (5)	0.0089 (5)
C1	0.0243 (7)	0.0255 (8)	0.0250 (7)	−0.0014 (6)	0.0017 (6)	0.0009 (6)
C2	0.0226 (7)	0.0204 (7)	0.0276 (8)	−0.0032 (6)	−0.0001 (6)	0.0003 (6)
C3	0.0267 (7)	0.0214 (7)	0.0245 (7)	−0.0049 (6)	−0.0012 (6)	−0.0004 (6)
C4	0.0317 (8)	0.0298 (8)	0.0261 (8)	−0.0004 (6)	0.0017 (6)	−0.0011 (6)
C5	0.0386 (9)	0.0395 (10)	0.0307 (8)	−0.0018 (7)	0.0074 (7)	−0.0055 (7)
C6	0.0503 (11)	0.0482 (11)	0.0236 (8)	−0.0117 (9)	0.0056 (7)	−0.0026 (8)
C7	0.0438 (10)	0.0421 (10)	0.0262 (8)	−0.0096 (8)	−0.0061 (7)	0.0056 (7)
C8	0.0308 (8)	0.0282 (8)	0.0278 (8)	−0.0075 (7)	−0.0046 (6)	0.0032 (6)
C9	0.0304 (9)	0.0335 (9)	0.0386 (9)	−0.0035 (7)	−0.0093 (7)	0.0097 (7)
C10	0.0220 (8)	0.0305 (9)	0.0463 (10)	−0.0009 (6)	−0.0017 (7)	0.0061 (7)
C11	0.0240 (8)	0.0245 (8)	0.0331 (8)	−0.0040 (6)	0.0030 (6)	0.0009 (6)
C12	0.0271 (8)	0.0302 (8)	0.0311 (8)	−0.0032 (6)	0.0043 (6)	0.0011 (7)
C13	0.0249 (7)	0.0249 (8)	0.0228 (7)	0.0008 (6)	−0.0024 (6)	0.0007 (6)
C14	0.0316 (8)	0.0280 (8)	0.0293 (8)	0.0053 (6)	0.0015 (6)	−0.0006 (6)
C15	0.0471 (10)	0.0254 (8)	0.0311 (8)	−0.0008 (7)	−0.0009 (7)	−0.0016 (7)
C16	0.0410 (10)	0.0359 (10)	0.0318 (8)	−0.0107 (8)	0.0003 (7)	0.0023 (7)
C17	0.0304 (9)	0.0425 (10)	0.0355 (9)	−0.0028 (7)	0.0065 (7)	−0.0031 (8)
C18	0.0290 (8)	0.0297 (8)	0.0309 (8)	0.0021 (6)	0.0015 (6)	−0.0058 (7)
C19	0.0415 (10)	0.0521 (12)	0.0335 (9)	−0.0013 (9)	0.0154 (8)	0.0001 (8)

S—O2	1.4387 (12)	C8—C9	1.426 (2)
S—O3	1.4403 (12)	C9—C10	1.355 (2)
S—C1	1.7492 (15)	C9—H9	0.9500
S—C13	1.7729 (16)	C10—C11	1.400 (2)
O1—C12	1.366 (2)	C10—H10	0.9500
O1—C11	1.3713 (19)	C12—C19	1.482 (2)
C1—C12	1.367 (2)	C13—C18	1.383 (2)
C1—C2	1.460 (2)	C13—C14	1.393 (2)
C2—C11	1.381 (2)	C14—C15	1.384 (2)
C2—C3	1.434 (2)	C14—H14	0.9500
C3—C4	1.412 (2)	C15—C16	1.389 (3)
C3—C8	1.434 (2)	C15—H15	0.9500
C4—C5	1.376 (2)	C16—C17	1.379 (3)
C4—H4	0.9500	C16—H16	0.9500
C5—C6	1.405 (3)	C17—C18	1.388 (2)
C5—H5	0.9500	C17—H17	0.9500
C6—C7	1.359 (3)	C18—H18	0.9500
C6—H6	0.9500	C19—H19A	0.9800
C7—C8	1.418 (2)	C19—H19B	0.9800
C7—H7	0.9500	C19—H19C	0.9800
Cg1···Cg2i	3.850 (2)
O2—S—O3	117.93 (7)	C9—C10—C11	116.63 (15)
O2—S—C1	110.28 (7)	C9—C10—H10	121.7
O3—S—C1	108.10 (7)	C11—C10—H10	121.7
O2—S—C13	107.14 (7)	O1—C11—C2	111.47 (13)
O3—S—C13	107.81 (7)	O1—C11—C10	122.77 (14)
C1—S—C13	104.76 (7)	C2—C11—C10	125.75 (15)
C12—O1—C11	107.16 (12)	O1—C12—C1	109.97 (14)
C12—C1—C2	107.47 (14)	O1—C12—C19	114.10 (14)
C12—C1—S	122.78 (12)	C1—C12—C19	135.93 (16)
C2—C1—S	129.59 (11)	C18—C13—C14	121.17 (15)
C11—C2—C3	118.11 (14)	C18—C13—S	118.24 (12)
C11—C2—C1	103.91 (13)	C14—C13—S	120.44 (12)
C3—C2—C1	137.99 (14)	C15—C14—C13	118.61 (15)
C4—C3—C2	125.03 (14)	C15—C14—H14	120.7
C4—C3—C8	118.22 (14)	C13—C14—H14	120.7
C2—C3—C8	116.75 (14)	C14—C15—C16	120.44 (16)
C5—C4—C3	121.14 (15)	C14—C15—H15	119.8
C5—C4—H4	119.4	C16—C15—H15	119.8
C3—C4—H4	119.4	C17—C16—C15	120.42 (16)
C4—C5—C6	120.51 (17)	C17—C16—H16	119.8
C4—C5—H5	119.7	C15—C16—H16	119.8
C6—C5—H5	119.7	C16—C17—C18	119.82 (16)
C7—C6—C5	119.84 (16)	C16—C17—H17	120.1
C7—C6—H6	120.1	C18—C17—H17	120.1
C5—C6—H6	120.1	C13—C18—C17	119.50 (16)
C6—C7—C8	121.71 (16)	C13—C18—H18	120.2
C6—C7—H7	119.1	C17—C18—H18	120.2
C8—C7—H7	119.1	C12—C19—H19A	109.5
C7—C8—C9	120.46 (15)	C12—C19—H19B	109.5
C7—C8—C3	118.54 (16)	H19A—C19—H19B	109.5
C9—C8—C3	120.99 (15)	C12—C19—H19C	109.5
C10—C9—C8	121.70 (15)	H19A—C19—H19C	109.5
C10—C9—H9	119.2	H19B—C19—H19C	109.5
C8—C9—H9	119.2
O2—S—C1—C12	136.48 (14)	C12—O1—C11—C2	1.42 (17)
O3—S—C1—C12	6.22 (17)	C12—O1—C11—C10	−177.49 (15)
C13—S—C1—C12	−108.55 (14)	C3—C2—C11—O1	179.31 (12)
O2—S—C1—C2	−48.68 (16)	C1—C2—C11—O1	−1.14 (17)
O3—S—C1—C2	−178.93 (14)	C3—C2—C11—C10	−1.8 (2)
C13—S—C1—C2	66.30 (16)	C1—C2—C11—C10	177.73 (15)
C12—C1—C2—C11	0.43 (17)	C9—C10—C11—O1	178.28 (15)
S—C1—C2—C11	−175.02 (12)	C9—C10—C11—C2	−0.5 (3)
C12—C1—C2—C3	179.84 (17)	C11—O1—C12—C1	−1.10 (18)
S—C1—C2—C3	4.4 (3)	C11—O1—C12—C19	178.68 (14)
C11—C2—C3—C4	−176.13 (15)	C2—C1—C12—O1	0.41 (18)
C1—C2—C3—C4	4.5 (3)	S—C1—C12—O1	176.24 (11)
C11—C2—C3—C8	3.3 (2)	C2—C1—C12—C19	−179.31 (19)
C1—C2—C3—C8	−176.09 (17)	S—C1—C12—C19	−3.5 (3)
C2—C3—C4—C5	−179.13 (15)	O2—S—C13—C18	−12.25 (14)
C8—C3—C4—C5	1.5 (2)	O3—S—C13—C18	115.62 (13)
C3—C4—C5—C6	0.5 (3)	C1—S—C13—C18	−129.41 (12)
C4—C5—C6—C7	−1.6 (3)	O2—S—C13—C14	172.06 (12)
C5—C6—C7—C8	0.7 (3)	O3—S—C13—C14	−60.06 (14)
C6—C7—C8—C9	−177.78 (17)	C1—S—C13—C14	54.91 (14)
C6—C7—C8—C3	1.3 (3)	C18—C13—C14—C15	0.9 (2)
C4—C3—C8—C7	−2.3 (2)	S—C13—C14—C15	176.46 (12)
C2—C3—C8—C7	178.25 (14)	C13—C14—C15—C16	−2.1 (2)
C4—C3—C8—C9	176.74 (15)	C14—C15—C16—C17	1.3 (3)
C2—C3—C8—C9	−2.7 (2)	C15—C16—C17—C18	0.8 (3)
C7—C8—C9—C10	179.50 (16)	C14—C13—C18—C17	1.1 (2)
C3—C8—C9—C10	0.5 (3)	S—C13—C18—C17	−174.55 (13)
C8—C9—C10—C11	1.1 (2)	C16—C17—C18—C13	−1.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2	0.95	2.35	3.190 (2)	147
C18—H18···O2	0.95	2.46	2.869 (2)	106
C19—H19B···O3	0.98	2.55	2.926 (2)	103
C19—H19C···Cg3i	0.98	3.03	3.735 (3)	130
C16—H16···Cg3ii	0.95	2.88	3.761 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2	0.95	2.35	3.190 (2)	147
C18—H18⋯O2	0.95	2.46	2.869 (2)	106
C19—H19B⋯O3	0.98	2.55	2.926 (2)	103
C19—H19C⋯Cg3i	0.98	3.03	3.735 (3)	130
C16—H16⋯Cg3ii	0.95	2.88	3.761 (3)	155

Symmetry codes: (i) ; (ii) . Cg3 is the centroid of the benzene ring of the naphthofuran unit.