2-Methyl-1-(methyl­sulfin­yl)naphtho[2,1-b]furan

The title compound, C₁₄H₁₂O₂S, was prepared by the oxidation of 2-methyl-1-(methyl­sulfan­yl)naphtho[2,1-b]furan using m-chloro­perbenzoic acid. The crystal structure contains aromatic π–π stacking, C—H...O and C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.065
• wR factor = 0.151
• Data-to-parameter ratio = 16.1

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-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.

2-Methyl-1-(methylsulfinyl)naphtho[2,1-b]furan

Crystal data

C14H12O2S	F(000) = 512
Mr = 244.30	Dx = 1.418 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3886 reflections
a = 8.3158 (7) Å	θ = 2.5–28.1°
b = 13.798 (1) Å	µ = 0.27 mm^−1
c = 10.3969 (8) Å	T = 120 K
β = 106.389 (1)°	Block, colourless
V = 1144.50 (15) Å^3	0.45 × 0.43 × 0.40 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer	2067 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.095
Graphite monochromator	θmax = 27.0°, θmin = 2.5°
φ and ω scans	h = −10→10
9694 measured reflections	k = −17→17
2495 independent reflections	l = −13→13

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.151	H-atom parameters constrained
S = 1.13	w = 1/[σ^2(Fo^2) + (0.052P)^2 + 1.6525P] where P = (Fo^2 + 2Fc^2)/3
2495 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.59 e Å^−3
0 restraints	Δρmin = −0.44 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	0.09193 (9)	0.74556 (5)	0.06136 (7)	0.0214 (2)
O1	0.1832 (3)	1.00803 (15)	0.2044 (2)	0.0254 (5)
O2	−0.0091 (3)	0.72686 (15)	−0.0806 (2)	0.0273 (5)
C1	0.1424 (3)	0.86940 (19)	0.0850 (3)	0.0185 (5)
C2	0.2098 (3)	0.94113 (19)	0.0115 (3)	0.0185 (6)
C3	0.2536 (3)	0.9443 (2)	−0.1126 (3)	0.0195 (6)
C4	0.2295 (4)	0.8662 (2)	−0.2047 (3)	0.0212 (6)
H4	0.1786	0.8094	−0.1879	0.025*
C5	0.2811 (4)	0.8743 (2)	−0.3188 (3)	0.0274 (7)
H5	0.2662	0.8223	−0.3780	0.033*
C6	0.3560 (4)	0.9600 (2)	−0.3473 (3)	0.0305 (7)
H6	0.3918	0.9640	−0.4242	0.037*
C7	0.3762 (4)	1.0372 (2)	−0.2621 (3)	0.0280 (7)
H7	0.4238	1.0941	−0.2826	0.034*
C8	0.3255 (3)	1.0321 (2)	−0.1428 (3)	0.0229 (6)
C9	0.3460 (4)	1.1135 (2)	−0.0547 (3)	0.0276 (7)
H9	0.3933	1.1700	−0.0768	0.033*
C10	0.2985 (4)	1.1113 (2)	0.0604 (3)	0.0270 (7)
H10	0.3095	1.1650	0.1162	0.032*
C11	0.2322 (4)	1.0236 (2)	0.0899 (3)	0.0222 (6)
C12	0.1292 (4)	0.9143 (2)	0.1981 (3)	0.0232 (6)
C13	0.0742 (4)	0.8803 (2)	0.3151 (3)	0.0305 (7)
H13A	−0.0160	0.9203	0.3248	0.037*
H13B	0.1665	0.8844	0.3950	0.037*
H13C	0.0369	0.8143	0.3009	0.037*
C14	0.2984 (4)	0.6988 (2)	0.0786 (3)	0.0279 (7)
H14A	0.2929	0.6297	0.0674	0.042*
H14B	0.3699	0.7144	0.1661	0.042*
H14C	0.3429	0.7273	0.0116	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.0238 (4)	0.0198 (4)	0.0227 (4)	−0.0039 (3)	0.0098 (3)	−0.0002 (3)
O1	0.0262 (11)	0.0257 (11)	0.0239 (10)	0.0013 (8)	0.0062 (9)	−0.0075 (8)
O2	0.0240 (11)	0.0263 (11)	0.0306 (11)	−0.0040 (8)	0.0062 (9)	−0.0074 (9)
C1	0.0185 (14)	0.0200 (13)	0.0164 (12)	−0.0006 (11)	0.0040 (10)	−0.0009 (10)
C2	0.0162 (13)	0.0171 (13)	0.0194 (13)	0.0024 (10)	0.0007 (11)	0.0001 (10)
C3	0.0152 (13)	0.0207 (13)	0.0222 (13)	0.0030 (10)	0.0044 (11)	0.0032 (11)
C4	0.0225 (15)	0.0223 (14)	0.0184 (13)	−0.0023 (11)	0.0051 (11)	0.0024 (11)
C5	0.0294 (17)	0.0319 (16)	0.0207 (14)	−0.0013 (13)	0.0069 (13)	0.0009 (12)
C6	0.0296 (17)	0.0412 (18)	0.0238 (15)	0.0008 (14)	0.0125 (13)	0.0101 (13)
C7	0.0220 (15)	0.0274 (15)	0.0352 (16)	−0.0011 (12)	0.0093 (13)	0.0120 (13)
C8	0.0167 (14)	0.0222 (14)	0.0285 (15)	0.0029 (11)	0.0043 (12)	0.0067 (12)
C9	0.0214 (15)	0.0157 (14)	0.0431 (18)	−0.0004 (11)	0.0050 (13)	0.0050 (12)
C10	0.0238 (16)	0.0172 (14)	0.0380 (17)	0.0028 (11)	0.0053 (13)	−0.0057 (12)
C11	0.0188 (14)	0.0227 (14)	0.0240 (14)	0.0046 (11)	0.0045 (11)	−0.0018 (11)
C12	0.0201 (15)	0.0258 (15)	0.0214 (14)	0.0020 (11)	0.0024 (12)	−0.0005 (11)
C13	0.0342 (18)	0.0408 (18)	0.0167 (14)	0.0042 (14)	0.0073 (13)	−0.0016 (12)
C14	0.0265 (16)	0.0234 (15)	0.0319 (16)	0.0048 (12)	0.0054 (13)	0.0055 (12)

Geometric parameters (Å, º)

S—O2	1.501 (2)	C6—H6	0.930
S—C1	1.760 (3)	C7—C8	1.420 (4)
S—C14	1.796 (3)	C7—H7	0.930
O1—C12	1.365 (4)	C8—C9	1.429 (4)
O1—C11	1.380 (3)	C9—C10	1.362 (4)
C1—C12	1.361 (4)	C9—H9	0.930
C1—C2	1.456 (4)	C10—C11	1.399 (4)
C2—C11	1.382 (4)	C10—H10	0.930
C2—C3	1.436 (4)	C12—C13	1.491 (4)
C3—C4	1.418 (4)	C13—H13A	0.960
C3—C8	1.425 (4)	C13—H13B	0.960
C4—C5	1.375 (4)	C13—H13C	0.960
C4—H4	0.930	C14—H14A	0.960
C5—C6	1.407 (4)	C14—H14B	0.960
C5—H5	0.930	C14—H14C	0.960
C6—C7	1.365 (5)
O2—S—C1	110.45 (12)	C7—C8—C9	120.6 (3)
O2—S—C14	106.89 (13)	C3—C8—C9	120.6 (3)
C1—S—C14	98.70 (14)	C10—C9—C8	122.2 (3)
C12—O1—C11	106.2 (2)	C10—C9—H9	118.9
C12—C1—C2	106.3 (2)	C8—C9—H9	118.9
C12—C1—S	119.2 (2)	C9—C10—C11	116.2 (3)
C2—C1—S	134.3 (2)	C9—C10—H10	121.9
C11—C2—C3	118.6 (3)	C11—C10—H10	121.9
C11—C2—C1	105.0 (2)	O1—C11—C2	110.9 (2)
C3—C2—C1	136.4 (2)	O1—C11—C10	123.7 (3)
C4—C3—C8	119.1 (2)	C2—C11—C10	125.4 (3)
C4—C3—C2	124.1 (2)	C1—C12—O1	111.6 (2)
C8—C3—C2	116.9 (2)	C1—C12—C13	132.9 (3)
C5—C4—C3	120.1 (3)	O1—C12—C13	115.5 (2)
C5—C4—H4	119.9	C12—C13—H13A	109.5
C3—C4—H4	119.9	C12—C13—H13B	109.5
C4—C5—C6	121.0 (3)	H13A—C13—H13B	109.5
C4—C5—H5	119.5	C12—C13—H13C	109.5
C6—C5—H5	119.5	H13A—C13—H13C	109.5
C7—C6—C5	120.0 (3)	H13B—C13—H13C	109.5
C7—C6—H6	120.0	S—C14—H14A	109.5
C5—C6—H6	120.0	S—C14—H14B	109.5
C6—C7—C8	121.0 (3)	H14A—C14—H14B	109.5
C6—C7—H7	119.5	S—C14—H14C	109.5
C8—C7—H7	119.5	H14A—C14—H14C	109.5
C7—C8—C3	118.8 (3)	H14B—C14—H14C	109.5
O2—S—C1—C12	137.1 (2)	C2—C3—C8—C7	177.8 (3)
C14—S—C1—C12	−111.2 (3)	C4—C3—C8—C9	177.6 (3)
O2—S—C1—C2	−47.6 (3)	C2—C3—C8—C9	−2.3 (4)
C14—S—C1—C2	64.2 (3)	C7—C8—C9—C10	179.8 (3)
C12—C1—C2—C11	0.5 (3)	C3—C8—C9—C10	0.0 (4)
S—C1—C2—C11	−175.3 (2)	C8—C9—C10—C11	1.6 (4)
C12—C1—C2—C3	−179.5 (3)	C12—O1—C11—C2	0.1 (3)
S—C1—C2—C3	4.7 (5)	C12—O1—C11—C10	−178.8 (3)
C11—C2—C3—C4	−177.0 (3)	C3—C2—C11—O1	179.7 (2)
C1—C2—C3—C4	3.0 (5)	C1—C2—C11—O1	−0.3 (3)
C11—C2—C3—C8	3.0 (4)	C3—C2—C11—C10	−1.5 (4)
C1—C2—C3—C8	−177.0 (3)	C1—C2—C11—C10	178.5 (3)
C8—C3—C4—C5	2.5 (4)	C9—C10—C11—O1	177.8 (3)
C2—C3—C4—C5	−177.5 (3)	C9—C10—C11—C2	−0.9 (4)
C3—C4—C5—C6	−1.0 (4)	C2—C1—C12—O1	−0.5 (3)
C4—C5—C6—C7	−1.0 (5)	S—C1—C12—O1	176.08 (19)
C5—C6—C7—C8	1.3 (5)	C2—C1—C12—C13	−178.0 (3)
C6—C7—C8—C3	0.3 (4)	S—C1—C12—C13	−1.4 (5)
C6—C7—C8—C9	−179.5 (3)	C11—O1—C12—C1	0.3 (3)
C4—C3—C8—C7	−2.2 (4)	C11—O1—C12—C13	178.2 (2)