1-Methyl­sulfinyl-2-phenyl­naphtho[2,1-b]furan

The title compound, C₁₉H₁₄O₂S, was prepared by oxidation of 1-methyl­sulfanyl-2-phenyl­naphtho[2,1-b]furan using 3-chloro­perbenzoic acid. The naphthofuran ring system is approximately planar. The crystal structure includes aromatic π–π stacking and C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.046
• wR factor = 0.114
• Data-to-parameter ratio = 15.8

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP III (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

C19H14O2S	F(000) = 640
Mr = 306.36	Dx = 1.407 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4941 reflections
a = 10.868 (1) Å	θ = 2.5–28.3°
b = 9.410 (1) Å	µ = 0.23 mm^−1
c = 14.190 (2) Å	T = 173 K
β = 94.568 (2)°	Plate, colourless
V = 1446.6 (3) Å^3	0.52 × 0.34 × 0.12 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer	2751 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.055
Graphite monochromator	θmax = 27.0°, θmin = 2.3°
φ and ω scans	h = −9→13
8612 measured reflections	k = −11→12
3151 independent reflections	l = −18→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.114	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0417P)^2 + 1.0385P] where P = (Fo^2 + 2Fc^2)/3
3151 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.49 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S	0.22562 (4)	0.25676 (5)	0.52687 (3)	0.02456 (14)
O1	0.13002 (12)	0.57658 (14)	0.35901 (9)	0.0264 (3)
O2	0.30767 (13)	0.15046 (15)	0.48484 (10)	0.0318 (3)
C1	0.16516 (16)	0.3684 (2)	0.43463 (12)	0.0212 (4)
C2	0.12569 (16)	0.3368 (2)	0.33632 (13)	0.0236 (4)
C3	0.10200 (17)	0.2116 (2)	0.28006 (13)	0.0245 (4)
C4	0.12240 (18)	0.0706 (2)	0.31168 (14)	0.0284 (4)
H4	0.1563	0.0544	0.3730	0.034*
C5	0.09293 (19)	−0.0430 (2)	0.25336 (15)	0.0339 (5)
H5	0.1070	−0.1351	0.2755	0.041*
C6	0.0416 (2)	−0.0207 (3)	0.16030 (15)	0.0367 (5)
H6	0.0199	−0.0979	0.1216	0.044*
C7	0.02375 (19)	0.1138 (3)	0.12689 (15)	0.0344 (5)
H7	−0.0091	0.1272	0.0650	0.041*
C8	0.05409 (17)	0.2341 (2)	0.18418 (14)	0.0288 (4)
C9	0.03831 (19)	0.3745 (2)	0.14708 (14)	0.0317 (5)
H9	0.0087	0.3856	0.0842	0.038*
C10	0.06484 (18)	0.4923 (2)	0.20002 (14)	0.0301 (4)
H10	0.0562	0.5833	0.1749	0.036*
C11	0.10620 (17)	0.4684 (2)	0.29508 (13)	0.0255 (4)
C12	0.16572 (16)	0.5130 (2)	0.44424 (13)	0.0232 (4)
C13	0.19585 (16)	0.6094 (2)	0.52321 (13)	0.0231 (4)
C14	0.24706 (18)	0.7429 (2)	0.50751 (15)	0.0285 (4)
H14	0.2601	0.7710	0.4463	0.034*
C15	0.2784 (2)	0.8332 (2)	0.58248 (16)	0.0346 (5)
H15	0.3133	0.9214	0.5715	0.042*
C16	0.2580 (2)	0.7929 (2)	0.67383 (16)	0.0375 (5)
H16	0.2797	0.8536	0.7241	0.045*
C17	0.2053 (2)	0.6623 (2)	0.69021 (15)	0.0335 (5)
H17	0.1909	0.6358	0.7515	0.040*
C18	0.17390 (18)	0.5714 (2)	0.61588 (14)	0.0273 (4)
H18	0.1379	0.4841	0.6274	0.033*
C19	0.0858 (2)	0.1667 (2)	0.55185 (16)	0.0343 (5)
H19A	0.1035	0.0997	0.6022	0.051*
H19B	0.0527	0.1173	0.4963	0.051*
H19C	0.0266	0.2349	0.5704	0.051*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.0281 (3)	0.0212 (2)	0.0238 (2)	0.00097 (18)	−0.00103 (18)	0.00331 (18)
O1	0.0313 (7)	0.0214 (7)	0.0262 (7)	0.0006 (5)	0.0008 (5)	0.0043 (5)
O2	0.0314 (7)	0.0286 (8)	0.0348 (8)	0.0074 (6)	−0.0004 (6)	0.0017 (6)
C1	0.0216 (8)	0.0209 (9)	0.0208 (8)	−0.0004 (7)	0.0009 (7)	0.0028 (7)
C2	0.0202 (9)	0.0265 (10)	0.0239 (9)	0.0002 (7)	0.0005 (7)	0.0031 (8)
C3	0.0205 (9)	0.0283 (10)	0.0249 (9)	−0.0008 (7)	0.0026 (7)	−0.0022 (8)
C4	0.0294 (10)	0.0290 (11)	0.0270 (10)	−0.0018 (8)	0.0025 (8)	−0.0020 (8)
C5	0.0360 (11)	0.0289 (11)	0.0377 (11)	−0.0032 (9)	0.0089 (9)	−0.0056 (9)
C6	0.0368 (11)	0.0389 (12)	0.0347 (11)	−0.0078 (10)	0.0057 (9)	−0.0157 (10)
C7	0.0306 (10)	0.0471 (13)	0.0252 (10)	−0.0021 (9)	0.0005 (8)	−0.0080 (9)
C8	0.0234 (9)	0.0382 (12)	0.0248 (9)	0.0012 (8)	0.0025 (7)	−0.0034 (8)
C9	0.0296 (10)	0.0429 (12)	0.0220 (9)	0.0057 (9)	−0.0014 (8)	0.0031 (9)
C10	0.0312 (10)	0.0320 (11)	0.0270 (10)	0.0038 (8)	0.0016 (8)	0.0087 (8)
C11	0.0242 (9)	0.0257 (10)	0.0268 (9)	0.0006 (8)	0.0035 (7)	0.0011 (8)
C12	0.0227 (9)	0.0228 (9)	0.0241 (9)	−0.0003 (7)	0.0027 (7)	0.0055 (7)
C13	0.0211 (9)	0.0194 (9)	0.0290 (9)	0.0009 (7)	0.0025 (7)	−0.0009 (7)
C14	0.0291 (10)	0.0220 (10)	0.0348 (10)	−0.0005 (8)	0.0045 (8)	0.0049 (8)
C15	0.0379 (11)	0.0196 (10)	0.0460 (12)	−0.0040 (8)	0.0008 (9)	−0.0008 (9)
C16	0.0452 (13)	0.0268 (11)	0.0397 (12)	−0.0010 (9)	−0.0016 (10)	−0.0101 (9)
C17	0.0418 (12)	0.0314 (11)	0.0281 (10)	0.0006 (9)	0.0072 (9)	−0.0028 (9)
C18	0.0304 (10)	0.0210 (10)	0.0311 (10)	−0.0019 (8)	0.0063 (8)	0.0008 (8)
C19	0.0367 (11)	0.0281 (11)	0.0394 (12)	−0.0024 (9)	0.0112 (9)	0.0070 (9)

Geometric parameters (Å, º)

S—O2	1.4954 (15)	C9—C10	1.357 (3)
S—C1	1.7641 (18)	C9—H9	0.930
S—C19	1.800 (2)	C10—C11	1.406 (3)
O1—C11	1.374 (2)	C10—H10	0.930
O1—C12	1.377 (2)	C12—C13	1.459 (3)
C1—C12	1.367 (3)	C13—C14	1.399 (3)
C1—C2	1.457 (2)	C13—C18	1.402 (3)
C2—C11	1.379 (3)	C14—C15	1.383 (3)
C2—C3	1.435 (3)	C14—H14	0.930
C3—C4	1.413 (3)	C15—C16	1.385 (3)
C3—C8	1.433 (3)	C15—H15	0.930
C4—C5	1.374 (3)	C16—C17	1.383 (3)
C4—H4	0.930	C16—H16	0.930
C5—C6	1.408 (3)	C17—C18	1.379 (3)
C5—H5	0.930	C17—H17	0.930
C6—C7	1.360 (3)	C18—H18	0.930
C6—H6	0.930	C19—H19A	0.960
C7—C8	1.417 (3)	C19—H19B	0.960
C7—H7	0.930	C19—H19C	0.960
C8—C9	1.427 (3)
O2—S—C1	107.53 (8)	C9—C10—H10	122.0
O2—S—C19	107.64 (10)	C11—C10—H10	122.0
C1—S—C19	98.99 (9)	O1—C11—C2	111.76 (16)
C11—O1—C12	106.44 (14)	O1—C11—C10	122.97 (18)
C12—C1—C2	107.31 (16)	C2—C11—C10	125.27 (19)
C12—C1—S	121.35 (14)	C1—C12—O1	110.24 (16)
C2—C1—S	130.72 (14)	C1—C12—C13	133.99 (17)
C11—C2—C3	119.11 (17)	O1—C12—C13	115.77 (16)
C11—C2—C1	104.25 (16)	C14—C13—C18	118.57 (18)
C3—C2—C1	136.61 (17)	C14—C13—C12	120.27 (17)
C4—C3—C8	118.44 (18)	C18—C13—C12	121.17 (17)
C4—C3—C2	125.29 (17)	C15—C14—C13	120.42 (19)
C8—C3—C2	116.27 (18)	C15—C14—H14	119.8
C5—C4—C3	121.09 (19)	C13—C14—H14	119.8
C5—C4—H4	119.5	C14—C15—C16	120.21 (19)
C3—C4—H4	119.5	C14—C15—H15	119.9
C4—C5—C6	120.3 (2)	C16—C15—H15	119.9
C4—C5—H5	119.8	C17—C16—C15	120.0 (2)
C6—C5—H5	119.8	C17—C16—H16	120.0
C7—C6—C5	120.1 (2)	C15—C16—H16	120.0
C7—C6—H6	120.0	C18—C17—C16	120.2 (2)
C5—C6—H6	120.0	C18—C17—H17	119.9
C6—C7—C8	121.54 (19)	C16—C17—H17	119.9
C6—C7—H7	119.2	C17—C18—C13	120.61 (19)
C8—C7—H7	119.2	C17—C18—H18	119.7
C7—C8—C9	120.79 (18)	C13—C18—H18	119.7
C7—C8—C3	118.49 (19)	S—C19—H19A	109.5
C9—C8—C3	120.72 (18)	S—C19—H19B	109.5
C10—C9—C8	122.53 (18)	H19A—C19—H19B	109.5
C10—C9—H9	118.7	S—C19—H19C	109.5
C8—C9—H9	118.7	H19A—C19—H19C	109.5
C9—C10—C11	116.00 (19)	H19B—C19—H19C	109.5
O2—S—C1—C12	−132.55 (16)	C12—O1—C11—C2	−0.1 (2)
C19—S—C1—C12	115.63 (17)	C12—O1—C11—C10	178.74 (18)
O2—S—C1—C2	37.20 (19)	C3—C2—C11—O1	178.39 (16)
C19—S—C1—C2	−74.62 (19)	C1—C2—C11—O1	0.0 (2)
C12—C1—C2—C11	0.2 (2)	C3—C2—C11—C10	−0.5 (3)
S—C1—C2—C11	−170.63 (15)	C1—C2—C11—C10	−178.89 (18)
C12—C1—C2—C3	−177.8 (2)	C9—C10—C11—O1	−176.18 (17)
S—C1—C2—C3	11.4 (3)	C9—C10—C11—C2	2.6 (3)
C11—C2—C3—C4	177.35 (19)	C2—C1—C12—O1	−0.3 (2)
C1—C2—C3—C4	−4.9 (3)	S—C1—C12—O1	171.57 (12)
C11—C2—C3—C8	−2.5 (3)	C2—C1—C12—C13	−179.95 (19)
C1—C2—C3—C8	175.3 (2)	S—C1—C12—C13	−8.1 (3)
C8—C3—C4—C5	−2.4 (3)	C11—O1—C12—C1	0.3 (2)
C2—C3—C4—C5	177.78 (19)	C11—O1—C12—C13	180.00 (15)
C3—C4—C5—C6	0.1 (3)	C1—C12—C13—C14	147.9 (2)
C4—C5—C6—C7	1.6 (3)	O1—C12—C13—C14	−31.8 (2)
C5—C6—C7—C8	−0.9 (3)	C1—C12—C13—C18	−32.5 (3)
C6—C7—C8—C9	178.0 (2)	O1—C12—C13—C18	147.91 (17)
C6—C7—C8—C3	−1.4 (3)	C18—C13—C14—C15	1.8 (3)
C4—C3—C8—C7	3.0 (3)	C12—C13—C14—C15	−178.48 (18)
C2—C3—C8—C7	−177.13 (17)	C13—C14—C15—C16	−0.8 (3)
C4—C3—C8—C9	−176.46 (18)	C14—C15—C16—C17	−0.5 (3)
C2—C3—C8—C9	3.4 (3)	C15—C16—C17—C18	0.6 (3)
C7—C8—C9—C10	179.1 (2)	C16—C17—C18—C13	0.5 (3)
C3—C8—C9—C10	−1.4 (3)	C14—C13—C18—C17	−1.7 (3)
C8—C9—C10—C11	−1.6 (3)	C12—C13—C18—C17	178.60 (18)