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

In the title mol-ecule, C(19)H(14)O(3)S, the phenyl ring forms a dihedral angle of 69.13 (6)° with the plane of the naphthofuran fragment, being slightly tilted towards it. The crystal packing exhibits π-π inter-actions between the benzene rings from neighbouring mol-ecules [centroid-centroid distance = 3.616 (4) Å] and weak C-H⋯O and C-H⋯π inter-actions.

Related literature

The crystal structure of 2-methyl-3-(methyl­sulfin­yl)naphtho[1,2-b]furan has been reported by Choi et al. (2006 ▶).

Experimental

Crystal data

C19H14O3S

M = 322.36

Orthorhombic,

a = 8.198 (4) Å

b = 18.589 (8) Å

c = 10.049 (4) Å

V = 1531.4 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 173 (2) K

0.40 × 0.30 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

8102 measured reflections

2714 independent reflections

2538 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.083

S = 1.05

2714 reflections

208 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 1125 Friedel pairs

Flack parameter: 0.04 (7)

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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/S1600536808000895/cv2379sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808000895/cv2379Isup2.hkl

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

C19H14O3S	F000 = 672
Mr = 322.36	Dx = 1.398 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5173 reflections
a = 8.198 (4) Å	θ = 2.2–28.1º
b = 18.589 (8) Å	µ = 0.22 mm−1
c = 10.049 (4) Å	T = 173 (2) K
V = 1531.4 (11) Å3	Block, yellow
Z = 4	0.40 × 0.30 × 0.20 mm

Bruker SMART CCD diffractometer	2714 independent reflections
Radiation source: fine-focus sealed tube	2538 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.048
Detector resolution: 10.0 pixels mm-1	θmax = 26.0º
T = 173(2) K	θmin = 2.2º
φ and ω scans	h = −7→10
Absorption correction: none	k = −22→22
8102 measured reflections	l = −12→11

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.031	w = 1/[σ2(Fo2) + (0.0507P)2 + 0.1234P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.083	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.26 e Å−3
2714 reflections	Δρmin = −0.21 e Å−3
208 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), 1125 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.04 (7)
Secondary atom site location: difference Fourier map

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
S1	0.44268 (6)	0.07870 (2)	0.60161 (6)	0.02617 (13)
O1	0.51082 (18)	0.27348 (7)	0.46110 (15)	0.0291 (3)
O2	0.3904 (2)	0.09804 (9)	0.73361 (15)	0.0373 (4)
O3	0.58124 (17)	0.03221 (8)	0.58544 (17)	0.0369 (4)
C1	0.4858 (2)	0.15710 (10)	0.5141 (2)	0.0253 (4)
C2	0.5822 (2)	0.16115 (11)	0.3939 (2)	0.0260 (4)
C3	0.6620 (3)	0.11149 (11)	0.3089 (2)	0.0293 (4)
H3	0.6565	0.0612	0.3254	0.035*
C4	0.7466 (3)	0.13772 (11)	0.2031 (2)	0.0314 (5)
H4	0.8012	0.1048	0.1460	0.038*
C5	0.7564 (3)	0.21297 (11)	0.1745 (2)	0.0296 (4)
C6	0.8432 (3)	0.23949 (14)	0.0629 (2)	0.0379 (5)
H6	0.8960	0.2067	0.0045	0.045*
C7	0.8521 (3)	0.31235 (14)	0.0381 (3)	0.0448 (6)
H7	0.9111	0.3293	−0.0370	0.054*
C8	0.7749 (3)	0.36149 (12)	0.1225 (3)	0.0421 (6)
H8	0.7828	0.4115	0.1042	0.051*
C9	0.6884 (3)	0.33880 (11)	0.2309 (2)	0.0342 (5)
H9	0.6355	0.3726	0.2872	0.041*
C10	0.6786 (3)	0.26389 (11)	0.2582 (2)	0.0276 (4)
C11	0.5932 (2)	0.23396 (10)	0.3665 (2)	0.0270 (4)
C12	0.4468 (2)	0.22595 (11)	0.5500 (2)	0.0282 (4)
C13	0.3579 (3)	0.25867 (13)	0.6634 (2)	0.0375 (5)
H13A	0.2672	0.2878	0.6297	0.045*
H13B	0.4325	0.2893	0.7143	0.045*
H13C	0.3154	0.2206	0.7211	0.045*
C14	0.2753 (2)	0.03853 (10)	0.51984 (19)	0.0249 (4)
C15	0.1181 (3)	0.05753 (12)	0.5593 (2)	0.0312 (5)
H15	0.1021	0.0928	0.6265	0.037*
C16	−0.0141 (3)	0.02474 (14)	0.5000 (2)	0.0404 (5)
H16	−0.1217	0.0368	0.5272	0.048*
C17	0.0105 (3)	−0.02571 (14)	0.4009 (3)	0.0469 (6)
H17	−0.0805	−0.0486	0.3604	0.056*
C18	0.1664 (3)	−0.04291 (13)	0.3605 (3)	0.0447 (6)
H18	0.1818	−0.0767	0.2908	0.054*
C19	0.3008 (3)	−0.01150 (11)	0.4204 (2)	0.0327 (5)
H19	0.4082	−0.0241	0.3937	0.039*

	U11	U22	U33	U12	U13	U23
S1	0.0274 (2)	0.0262 (2)	0.0250 (2)	−0.00075 (19)	−0.0024 (2)	0.0041 (2)
O1	0.0359 (8)	0.0213 (6)	0.0301 (8)	0.0009 (6)	0.0004 (6)	−0.0021 (6)
O2	0.0459 (9)	0.0419 (8)	0.0241 (8)	−0.0059 (8)	−0.0011 (7)	0.0014 (7)
O3	0.0300 (8)	0.0329 (7)	0.0477 (11)	0.0043 (6)	−0.0026 (7)	0.0125 (8)
C1	0.0254 (9)	0.0224 (9)	0.0282 (11)	−0.0009 (8)	−0.0043 (8)	0.0008 (8)
C2	0.0254 (10)	0.0265 (10)	0.0261 (10)	−0.0022 (8)	−0.0030 (8)	0.0021 (8)
C3	0.0337 (11)	0.0226 (9)	0.0317 (11)	−0.0016 (9)	−0.0024 (9)	−0.0003 (8)
C4	0.0356 (12)	0.0298 (10)	0.0290 (11)	0.0004 (9)	0.0012 (9)	−0.0030 (9)
C5	0.0321 (11)	0.0337 (11)	0.0229 (10)	−0.0027 (9)	−0.0040 (8)	0.0025 (9)
C6	0.0411 (13)	0.0454 (14)	0.0271 (12)	−0.0046 (11)	−0.0001 (9)	0.0043 (9)
C7	0.0469 (14)	0.0538 (15)	0.0337 (13)	−0.0117 (12)	−0.0025 (11)	0.0163 (11)
C8	0.0503 (14)	0.0320 (11)	0.0441 (15)	−0.0122 (10)	−0.0105 (11)	0.0122 (11)
C9	0.0381 (12)	0.0278 (10)	0.0366 (13)	−0.0050 (9)	−0.0084 (9)	0.0021 (9)
C10	0.0295 (11)	0.0272 (10)	0.0260 (10)	−0.0050 (8)	−0.0080 (8)	0.0046 (8)
C11	0.0287 (10)	0.0237 (10)	0.0286 (11)	−0.0013 (8)	−0.0042 (8)	−0.0021 (9)
C12	0.0280 (10)	0.0273 (10)	0.0294 (10)	−0.0001 (9)	−0.0032 (8)	−0.0012 (8)
C13	0.0426 (14)	0.0349 (12)	0.0349 (12)	0.0055 (10)	0.0026 (10)	−0.0042 (10)
C14	0.0282 (10)	0.0235 (9)	0.0229 (11)	−0.0014 (8)	0.0004 (8)	0.0052 (8)
C15	0.0327 (11)	0.0338 (10)	0.0271 (11)	0.0014 (10)	0.0036 (8)	0.0036 (8)
C16	0.0297 (11)	0.0534 (14)	0.0380 (14)	−0.0038 (11)	0.0007 (10)	0.0068 (11)
C17	0.0412 (14)	0.0608 (16)	0.0386 (14)	−0.0207 (13)	−0.0045 (11)	0.0009 (12)
C18	0.0576 (15)	0.0430 (13)	0.0335 (13)	−0.0117 (12)	0.0037 (11)	−0.0098 (11)
C19	0.0354 (12)	0.0311 (11)	0.0316 (11)	−0.0021 (9)	0.0058 (9)	−0.0032 (9)

S1—O3	1.437 (2)	C8—C9	1.367 (3)
S1—O2	1.440 (2)	C8—H8	0.9500
S1—C1	1.738 (2)	C9—C10	1.422 (3)
S1—C14	1.765 (2)	C9—H9	0.9500
O1—C12	1.361 (3)	C10—C11	1.409 (3)
O1—C11	1.378 (2)	C12—C13	1.483 (3)
C1—C12	1.368 (3)	C13—H13A	0.9800
C1—C2	1.446 (3)	C13—H13B	0.9800
C2—C11	1.384 (3)	C13—H13C	0.9800
C2—C3	1.418 (3)	C14—C19	1.381 (3)
C3—C4	1.360 (3)	C14—C15	1.394 (3)
C3—H3	0.9500	C15—C16	1.378 (3)
C4—C5	1.430 (3)	C15—H15	0.9500
C4—H4	0.9500	C16—C17	1.383 (4)
C5—C6	1.417 (3)	C16—H16	0.9500
C5—C10	1.417 (3)	C17—C18	1.379 (4)
C6—C7	1.379 (4)	C17—H17	0.9500
C6—H6	0.9500	C18—C19	1.384 (3)
C7—C8	1.398 (4)	C18—H18	0.9500
C7—H7	0.9500	C19—H19	0.9500
Cg2···Cg3i	3.616 (4)
O3—S1—O2	119.3 (1)	C11—C10—C5	114.7 (2)
O3—S1—C1	106.6 (1)	C11—C10—C9	124.3 (2)
O2—S1—C1	108.5 (1)	C5—C10—C9	121.0 (2)
O3—S1—C14	107.9 (1)	O1—C11—C2	110.6 (2)
O2—S1—C14	107.7 (1)	O1—C11—C10	124.5 (2)
C1—S1—C14	106.1 (1)	C2—C11—C10	124.9 (2)
C12—O1—C11	107.2 (2)	O1—C12—C1	110.2 (2)
C12—C1—C2	107.4 (2)	O1—C12—C13	115.3 (2)
C12—C1—S1	127.1 (2)	C1—C12—C13	134.5 (2)
C2—C1—S1	125.3 (2)	C12—C13—H13A	109.5
C11—C2—C3	119.1 (2)	C12—C13—H13B	109.5
C11—C2—C1	104.6 (2)	H13A—C13—H13B	109.5
C3—C2—C1	136.2 (2)	C12—C13—H13C	109.5
C4—C3—C2	118.2 (2)	H13A—C13—H13C	109.5
C4—C3—H3	120.9	H13B—C13—H13C	109.5
C2—C3—H3	120.9	C19—C14—C15	121.1 (2)
C3—C4—C5	122.4 (2)	C19—C14—S1	120.3 (2)
C3—C4—H4	118.8	C15—C14—S1	118.6 (2)
C5—C4—H4	118.8	C16—C15—C14	119.4 (2)
C6—C5—C10	117.6 (2)	C16—C15—H15	120.3
C6—C5—C4	121.8 (2)	C14—C15—H15	120.3
C10—C5—C4	120.6 (2)	C15—C16—C17	119.8 (2)
C7—C6—C5	120.8 (2)	C15—C16—H16	120.1
C7—C6—H6	119.6	C17—C16—H16	120.1
C5—C6—H6	119.6	C18—C17—C16	120.3 (2)
C6—C7—C8	120.5 (2)	C18—C17—H17	119.9
C6—C7—H7	119.7	C16—C17—H17	119.9
C8—C7—H7	119.7	C17—C18—C19	120.8 (2)
C9—C8—C7	121.1 (2)	C17—C18—H18	119.6
C9—C8—H8	119.4	C19—C18—H18	119.6
C7—C8—H8	119.4	C14—C19—C18	118.5 (2)
C8—C9—C10	119.0 (2)	C14—C19—H19	120.7
C8—C9—H9	120.5	C18—C19—H19	120.7
C10—C9—H9	120.5
O3—S1—C1—C12	−142.38 (19)	C3—C2—C11—O1	−178.86 (17)
O2—S1—C1—C12	−12.7 (2)	C1—C2—C11—O1	0.0 (2)
C14—S1—C1—C12	102.8 (2)	C3—C2—C11—C10	0.2 (3)
O3—S1—C1—C2	32.34 (19)	C1—C2—C11—C10	179.12 (19)
O2—S1—C1—C2	162.06 (16)	C5—C10—C11—O1	179.07 (18)
C14—S1—C1—C2	−82.51 (18)	C9—C10—C11—O1	−1.2 (3)
C12—C1—C2—C11	−0.1 (2)	C5—C10—C11—C2	0.1 (3)
S1—C1—C2—C11	−175.74 (15)	C9—C10—C11—C2	179.8 (2)
C12—C1—C2—C3	178.5 (2)	C11—O1—C12—C1	−0.2 (2)
S1—C1—C2—C3	2.9 (3)	C11—O1—C12—C13	177.78 (17)
C11—C2—C3—C4	0.0 (3)	C2—C1—C12—O1	0.2 (2)
C1—C2—C3—C4	−178.5 (2)	S1—C1—C12—O1	175.70 (14)
C2—C3—C4—C5	−0.5 (3)	C2—C1—C12—C13	−177.2 (2)
C3—C4—C5—C6	−179.2 (2)	S1—C1—C12—C13	−1.7 (4)
C3—C4—C5—C10	0.9 (3)	O3—S1—C14—C19	−22.04 (19)
C10—C5—C6—C7	0.5 (3)	O2—S1—C14—C19	−152.05 (17)
C4—C5—C6—C7	−179.5 (2)	C1—S1—C14—C19	91.94 (18)
C5—C6—C7—C8	−0.2 (4)	O3—S1—C14—C15	156.92 (16)
C6—C7—C8—C9	−0.4 (4)	O2—S1—C14—C15	26.90 (19)
C7—C8—C9—C10	0.6 (3)	C1—S1—C14—C15	−89.10 (18)
C6—C5—C10—C11	179.43 (18)	C19—C14—C15—C16	1.4 (3)
C4—C5—C10—C11	−0.6 (3)	S1—C14—C15—C16	−177.59 (17)
C6—C5—C10—C9	−0.3 (3)	C14—C15—C16—C17	−1.0 (3)
C4—C5—C10—C9	179.69 (19)	C15—C16—C17—C18	−0.5 (4)
C8—C9—C10—C11	−179.9 (2)	C16—C17—C18—C19	1.6 (4)
C8—C9—C10—C5	−0.3 (3)	C15—C14—C19—C18	−0.2 (3)
C12—O1—C11—C2	0.1 (2)	S1—C14—C19—C18	178.69 (18)
C12—O1—C11—C10	−178.99 (19)	C17—C18—C19—C14	−1.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···Cg1i	0.98	2.64	3.483 (3)	144
C8—H8···O3ii	0.95	2.51	3.406 (3)	157
C16—H16···O3iii	0.95	2.51	3.430 (3)	164

Table 1

Selected interatomic distances (Å)

Cg2 and Cg3 are the centroids of the C2–C5/C10/C11 benzene ring and the C5–C10 benzene ring, respectively.

Cg2⋯Cg3i

3.616 (4)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the O1/C12/C1/C2/C11 furan ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯Cg1i	0.98	2.64	3.483 (3)	144
C8—H8⋯O3ii	0.95	2.51	3.406 (3)	157
C16—H16⋯O3iii	0.95	2.51	3.430 (3)	164

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