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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): o452.
Published online 2008 January 16. doi:  10.1107/S1600536808000895
PMCID: PMC2960217

2-Methyl-3-(phenyl­sulfon­yl)naphtho[1,2-b]furan

Abstract

In the title mol­ecule, C19H14O3S, 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 inter­actions between the benzene rings from neighbouring mol­ecules [centroid–centroid distance = 3.616 (4) Å] and weak C—H(...)O and C—H(...)π inter­actions.

Related literature

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

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Object name is e-64-0o452-scheme1.jpg

Experimental

Crystal data

  • C19H14O3S
  • M r = 322.36
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o452-efi11.jpg
  • 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 [triangle]), 1125 Friedel pairs
  • Flack parameter: 0.04 (7)

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]) and DIAMOND (Brandenburg, 1998 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Selected interatomic distances (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

supplementary crystallographic information

Comment

As part of our ongoing study of 2-methylnaphtho[1,2-b]furan derivatives, the crystal structure of 2-methyl-3-(methylsulfinyl)naphtho[1,2-b]furan has been recently reported (Choi et al., 2006). Herein we present the molecular and crystal structure of the title compound, (I).

In (I) (Fig. 1), the naphthofuran unit is essentially planar, with a mean deviation of 0.007 Å from the least-squares plane defined by the thirteen constituent atoms. The crystal packing (Fig. 2) is stabilized by aromatic π—π stacking interactions between adjacent benzene rings. The Cg2···Cg3i distance is 3.616 (4) Å (Table 1; Cg2 and Cg3 are the centroids of the C2—C5/C10/C11 benzene ring and the C5—C10 benzene ring, respectively, symmetry code as in Fig. 2). The molecular packing is further stabilized by CH2—H···π interactions between the methyl group and the furan ring of the naphthofuran unit, with a C13—H13A···Cg1i separation of 2.64 Å (Fig. 2 and Table 2; Cg1 is the centroid of the O1/C12/C1/C2/C11 furan ring; symmetry code as in Fig. 2). Additionally, the weak hydrogen bonds were observed; one between the benzene H atom of naphthofuran unit and the O atom of sulfonyl group, with a C8—H8···O3ii, a second between the benzene H atom of phenylsulfonyl group and adjacent O atom of sulfonyl group, with a C16—H16···O3iii (Fig. 2 and Table 2; symmetry code as in Fig. 2).

Experimental

3-Chloroperbenzoic acid (77%, 560 mg, 2.5 mmol) was added in small portions to a stirred solution of 2-methyl-3-(phenylsulfanyl)naphtho[1,2-b] furan (348 mg, 1.2 mmol) in dichloromethane (40 ml) at 273 K. After being stirred at room temperature for 4 h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by column chromatography (hexane-ethyl acetate, 2:1 v/v) to afford the title compound as a pale yellow solid [yield 84%, m.p. 412–413 K; Rf = 0.64 (hexane-ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a dilute solution of the title compound in acetone at room temperature.

Refinement

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å for aromatic H atoms and 0.98 Å for methyl H atoms, respectively, and with Uiso(H) = 1.2Ueq(C) for all H atoms.

Figures

Fig. 1.
The molecular structure of the title compound, showing displacement ellipsoides drawn at the 50% probability level.
Fig. 2.
π—π, C—H···π and C—H···O interactions (dotted lines) in the title compound [symmetry codes: (i) x - 1/2, -y + 1/2, z; (ii) -x + 3/2, y + 1/2, z - 1/2; (iii) ...

Crystal data

C19H14O3SF000 = 672
Mr = 322.36Dx = 1.398 Mg m3
Orthorhombic, Pna21Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 5173 reflections
a = 8.198 (4) Åθ = 2.2–28.1º
b = 18.589 (8) ŵ = 0.22 mm1
c = 10.049 (4) ÅT = 173 (2) K
V = 1531.4 (11) Å3Block, yellow
Z = 40.40 × 0.30 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer2714 independent reflections
Radiation source: fine-focus sealed tube2538 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.048
Detector resolution: 10.0 pixels mm-1θmax = 26.0º
T = 173(2) Kθmin = 2.2º
[var phi] and ω scansh = −7→10
Absorption correction: nonek = −22→22
8102 measured reflectionsl = −12→11

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.05Δρmax = 0.26 e Å3
2714 reflectionsΔρmin = −0.21 e Å3
208 parametersExtinction correction: none
1 restraintAbsolute structure: Flack (1983), 1125 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.04 (7)
Secondary atom site location: difference Fourier map

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 (Å2)

xyzUiso*/Ueq
S10.44268 (6)0.07870 (2)0.60161 (6)0.02617 (13)
O10.51082 (18)0.27348 (7)0.46110 (15)0.0291 (3)
O20.3904 (2)0.09804 (9)0.73361 (15)0.0373 (4)
O30.58124 (17)0.03221 (8)0.58544 (17)0.0369 (4)
C10.4858 (2)0.15710 (10)0.5141 (2)0.0253 (4)
C20.5822 (2)0.16115 (11)0.3939 (2)0.0260 (4)
C30.6620 (3)0.11149 (11)0.3089 (2)0.0293 (4)
H30.65650.06120.32540.035*
C40.7466 (3)0.13772 (11)0.2031 (2)0.0314 (5)
H40.80120.10480.14600.038*
C50.7564 (3)0.21297 (11)0.1745 (2)0.0296 (4)
C60.8432 (3)0.23949 (14)0.0629 (2)0.0379 (5)
H60.89600.20670.00450.045*
C70.8521 (3)0.31235 (14)0.0381 (3)0.0448 (6)
H70.91110.3293−0.03700.054*
C80.7749 (3)0.36149 (12)0.1225 (3)0.0421 (6)
H80.78280.41150.10420.051*
C90.6884 (3)0.33880 (11)0.2309 (2)0.0342 (5)
H90.63550.37260.28720.041*
C100.6786 (3)0.26389 (11)0.2582 (2)0.0276 (4)
C110.5932 (2)0.23396 (10)0.3665 (2)0.0270 (4)
C120.4468 (2)0.22595 (11)0.5500 (2)0.0282 (4)
C130.3579 (3)0.25867 (13)0.6634 (2)0.0375 (5)
H13A0.26720.28780.62970.045*
H13B0.43250.28930.71430.045*
H13C0.31540.22060.72110.045*
C140.2753 (2)0.03853 (10)0.51984 (19)0.0249 (4)
C150.1181 (3)0.05753 (12)0.5593 (2)0.0312 (5)
H150.10210.09280.62650.037*
C16−0.0141 (3)0.02474 (14)0.5000 (2)0.0404 (5)
H16−0.12170.03680.52720.048*
C170.0105 (3)−0.02571 (14)0.4009 (3)0.0469 (6)
H17−0.0805−0.04860.36040.056*
C180.1664 (3)−0.04291 (13)0.3605 (3)0.0447 (6)
H180.1818−0.07670.29080.054*
C190.3008 (3)−0.01150 (11)0.4204 (2)0.0327 (5)
H190.4082−0.02410.39370.039*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0274 (2)0.0262 (2)0.0250 (2)−0.00075 (19)−0.0024 (2)0.0041 (2)
O10.0359 (8)0.0213 (6)0.0301 (8)0.0009 (6)0.0004 (6)−0.0021 (6)
O20.0459 (9)0.0419 (8)0.0241 (8)−0.0059 (8)−0.0011 (7)0.0014 (7)
O30.0300 (8)0.0329 (7)0.0477 (11)0.0043 (6)−0.0026 (7)0.0125 (8)
C10.0254 (9)0.0224 (9)0.0282 (11)−0.0009 (8)−0.0043 (8)0.0008 (8)
C20.0254 (10)0.0265 (10)0.0261 (10)−0.0022 (8)−0.0030 (8)0.0021 (8)
C30.0337 (11)0.0226 (9)0.0317 (11)−0.0016 (9)−0.0024 (9)−0.0003 (8)
C40.0356 (12)0.0298 (10)0.0290 (11)0.0004 (9)0.0012 (9)−0.0030 (9)
C50.0321 (11)0.0337 (11)0.0229 (10)−0.0027 (9)−0.0040 (8)0.0025 (9)
C60.0411 (13)0.0454 (14)0.0271 (12)−0.0046 (11)−0.0001 (9)0.0043 (9)
C70.0469 (14)0.0538 (15)0.0337 (13)−0.0117 (12)−0.0025 (11)0.0163 (11)
C80.0503 (14)0.0320 (11)0.0441 (15)−0.0122 (10)−0.0105 (11)0.0122 (11)
C90.0381 (12)0.0278 (10)0.0366 (13)−0.0050 (9)−0.0084 (9)0.0021 (9)
C100.0295 (11)0.0272 (10)0.0260 (10)−0.0050 (8)−0.0080 (8)0.0046 (8)
C110.0287 (10)0.0237 (10)0.0286 (11)−0.0013 (8)−0.0042 (8)−0.0021 (9)
C120.0280 (10)0.0273 (10)0.0294 (10)−0.0001 (9)−0.0032 (8)−0.0012 (8)
C130.0426 (14)0.0349 (12)0.0349 (12)0.0055 (10)0.0026 (10)−0.0042 (10)
C140.0282 (10)0.0235 (9)0.0229 (11)−0.0014 (8)0.0004 (8)0.0052 (8)
C150.0327 (11)0.0338 (10)0.0271 (11)0.0014 (10)0.0036 (8)0.0036 (8)
C160.0297 (11)0.0534 (14)0.0380 (14)−0.0038 (11)0.0007 (10)0.0068 (11)
C170.0412 (14)0.0608 (16)0.0386 (14)−0.0207 (13)−0.0045 (11)0.0009 (12)
C180.0576 (15)0.0430 (13)0.0335 (13)−0.0117 (12)0.0037 (11)−0.0098 (11)
C190.0354 (12)0.0311 (11)0.0316 (11)−0.0021 (9)0.0058 (9)−0.0032 (9)

Geometric parameters (Å, °)

S1—O31.437 (2)C8—C91.367 (3)
S1—O21.440 (2)C8—H80.9500
S1—C11.738 (2)C9—C101.422 (3)
S1—C141.765 (2)C9—H90.9500
O1—C121.361 (3)C10—C111.409 (3)
O1—C111.378 (2)C12—C131.483 (3)
C1—C121.368 (3)C13—H13A0.9800
C1—C21.446 (3)C13—H13B0.9800
C2—C111.384 (3)C13—H13C0.9800
C2—C31.418 (3)C14—C191.381 (3)
C3—C41.360 (3)C14—C151.394 (3)
C3—H30.9500C15—C161.378 (3)
C4—C51.430 (3)C15—H150.9500
C4—H40.9500C16—C171.383 (4)
C5—C61.417 (3)C16—H160.9500
C5—C101.417 (3)C17—C181.379 (4)
C6—C71.379 (4)C17—H170.9500
C6—H60.9500C18—C191.384 (3)
C7—C81.398 (4)C18—H180.9500
C7—H70.9500C19—H190.9500
Cg2···Cg3i3.616 (4)
O3—S1—O2119.3 (1)C11—C10—C5114.7 (2)
O3—S1—C1106.6 (1)C11—C10—C9124.3 (2)
O2—S1—C1108.5 (1)C5—C10—C9121.0 (2)
O3—S1—C14107.9 (1)O1—C11—C2110.6 (2)
O2—S1—C14107.7 (1)O1—C11—C10124.5 (2)
C1—S1—C14106.1 (1)C2—C11—C10124.9 (2)
C12—O1—C11107.2 (2)O1—C12—C1110.2 (2)
C12—C1—C2107.4 (2)O1—C12—C13115.3 (2)
C12—C1—S1127.1 (2)C1—C12—C13134.5 (2)
C2—C1—S1125.3 (2)C12—C13—H13A109.5
C11—C2—C3119.1 (2)C12—C13—H13B109.5
C11—C2—C1104.6 (2)H13A—C13—H13B109.5
C3—C2—C1136.2 (2)C12—C13—H13C109.5
C4—C3—C2118.2 (2)H13A—C13—H13C109.5
C4—C3—H3120.9H13B—C13—H13C109.5
C2—C3—H3120.9C19—C14—C15121.1 (2)
C3—C4—C5122.4 (2)C19—C14—S1120.3 (2)
C3—C4—H4118.8C15—C14—S1118.6 (2)
C5—C4—H4118.8C16—C15—C14119.4 (2)
C6—C5—C10117.6 (2)C16—C15—H15120.3
C6—C5—C4121.8 (2)C14—C15—H15120.3
C10—C5—C4120.6 (2)C15—C16—C17119.8 (2)
C7—C6—C5120.8 (2)C15—C16—H16120.1
C7—C6—H6119.6C17—C16—H16120.1
C5—C6—H6119.6C18—C17—C16120.3 (2)
C6—C7—C8120.5 (2)C18—C17—H17119.9
C6—C7—H7119.7C16—C17—H17119.9
C8—C7—H7119.7C17—C18—C19120.8 (2)
C9—C8—C7121.1 (2)C17—C18—H18119.6
C9—C8—H8119.4C19—C18—H18119.6
C7—C8—H8119.4C14—C19—C18118.5 (2)
C8—C9—C10119.0 (2)C14—C19—H19120.7
C8—C9—H9120.5C18—C19—H19120.7
C10—C9—H9120.5
O3—S1—C1—C12−142.38 (19)C3—C2—C11—O1−178.86 (17)
O2—S1—C1—C12−12.7 (2)C1—C2—C11—O10.0 (2)
C14—S1—C1—C12102.8 (2)C3—C2—C11—C100.2 (3)
O3—S1—C1—C232.34 (19)C1—C2—C11—C10179.12 (19)
O2—S1—C1—C2162.06 (16)C5—C10—C11—O1179.07 (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—C20.1 (3)
S1—C1—C2—C11−175.74 (15)C9—C10—C11—C2179.8 (2)
C12—C1—C2—C3178.5 (2)C11—O1—C12—C1−0.2 (2)
S1—C1—C2—C32.9 (3)C11—O1—C12—C13177.78 (17)
C11—C2—C3—C40.0 (3)C2—C1—C12—O10.2 (2)
C1—C2—C3—C4−178.5 (2)S1—C1—C12—O1175.70 (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—C100.9 (3)O3—S1—C14—C19−22.04 (19)
C10—C5—C6—C70.5 (3)O2—S1—C14—C19−152.05 (17)
C4—C5—C6—C7−179.5 (2)C1—S1—C14—C1991.94 (18)
C5—C6—C7—C8−0.2 (4)O3—S1—C14—C15156.92 (16)
C6—C7—C8—C9−0.4 (4)O2—S1—C14—C1526.90 (19)
C7—C8—C9—C100.6 (3)C1—S1—C14—C15−89.10 (18)
C6—C5—C10—C11179.43 (18)C19—C14—C15—C161.4 (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—C9179.69 (19)C15—C16—C17—C18−0.5 (4)
C8—C9—C10—C11−179.9 (2)C16—C17—C18—C191.6 (4)
C8—C9—C10—C5−0.3 (3)C15—C14—C19—C18−0.2 (3)
C12—O1—C11—C20.1 (2)S1—C14—C19—C18178.69 (18)
C12—O1—C11—C10−178.99 (19)C17—C18—C19—C14−1.2 (4)

Symmetry codes: (i) x−1/2, −y+1/2, z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C13—H13A···Cg1i0.982.643.483 (3)144
C8—H8···O3ii0.952.513.406 (3)157
C16—H16···O3iii0.952.513.430 (3)164

Symmetry codes: (i) x−1/2, −y+1/2, z; (ii) −x+3/2, y+1/2, z−1/2; (iii) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2379).

References

  • Brandenburg, K. (1998). DIAMOND Version 2.1. Crystal Impact GbR, Bonn, Germany.
  • Bruker (1997). SMART (Version 5.631) and SAINT (Version 6.12). Bruker AXS Inc., Madison, Wisconsin, USA.
  • Choi, H. D., Woo, H. M., Seo, P. J., Son, B. W. & Lee, U. (2006). Acta Cryst. E62, o3883–o3884.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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