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ISSN: 2056-9890

1-(4-Bromo­phenyl­sulfin­yl)-2-methyl­naphtho­[2,1-b]furan

aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea, and bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
*Correspondence e-mail: uklee@pknu.ac.kr

(Received 21 March 2012; accepted 23 March 2012; online 31 March 2012)

In the title compound, C19H13BrO2S, the 4-bromo­phenyl ring makes a dihedral angle of 83.75 (4)° with the mean plane of the naphtho­furan fragment [r.m.s. deviation = 0.024 (2) Å]. In the crystal, mol­ecules are linked via pairs of C—H⋯O hydrogen bonds, forming inversion dimers. These dimers are connected by weak ππ inter­actions between the central naphtho­furan benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.483 (2) Å, inter­planar distance = 3.416 (2) Å and slippage = 0.680 (2) Å].

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2007[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007). Acta Cryst. E63, o1731-o1732.], 2012[Choi, H. D., Seo, P. J. & Lee, U. (2012). Acta Cryst. E68, o549.]).

[Scheme 1]

Experimental

Crystal data
  • C19H13BrO2S

  • Mr = 385.26

  • Triclinic, [P \overline 1]

  • a = 8.7124 (1) Å

  • b = 9.4857 (1) Å

  • c = 10.2898 (1) Å

  • α = 82.883 (1)°

  • β = 71.126 (1)°

  • γ = 75.672 (1)°

  • V = 778.74 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 2.78 mm−1

  • T = 173 K

  • 0.33 × 0.29 × 0.27 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.462, Tmax = 0.517

  • 14577 measured reflections

  • 3853 independent reflections

  • 3461 reflections with I > 2σ(I)

  • Rint = 0.031

Refinement
  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 0.080

  • S = 1.05

  • 3853 reflections

  • 209 parameters

  • H-atom parameters constrained

  • Δρmax = 0.62 e Å−3

  • Δρmin = −0.60 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C19—H19⋯O2i 0.95 2.35 3.221 (2) 152
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

As a part of our ongoing study of 2-methylnaphtho[2,1-b]furan derivatives containing 1-phenylsulfinyl (Choi et al., 2007) and 1-(4-methylphenylsulfinyl) (Choi et al., 2012) substituents, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the naphthofuran unit is essentially planar, with a mean deviation of 0.024 (2) Å from the least-squares plane defined by the thirteen constituent atoms. The dihedral angle between the 4-bromophenyl ring and the mean plane of the naphthofuran fragment is 83.75 (4)°. In the crystal structure, molecules are linked via pairs of C—H···O hydrogen bonds (Fig. 2 & Table 1), forming inversion dimers. These dimers are connected by weak ππ interactions between the central naphthofuran benzene rings of neighbouring molecules, with a Cg···Cgii distance of 3.483 (2) Å and an interplanar distance of 3.416 (2) Å resulting in a slippage of 0.680 (2) Å (Fig. 2, Cg is the centroid of the C2/C3/C8/C9/C10/C11 benzene ring).

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2007, 2012).

Experimental top

77% 3-Chloroperoxybenzoic acid (202 mg, 0.9 mmol) was added in small portions to a stirred solution of 1-(4-bromophenylsulfanyl)-2-methylnaphtho [2,1-b]furan (295 mg, 0.8 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 5h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane–ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 74%, m.p. 466–467 K; Rf = 0.59 (hexane–ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in acetone at room temperature.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å for aryl and 0.98 Å for the methyl H atoms. Uiso(H) = 1.2Ueq(C) for aryl and 1.5Ueq(C) for methyl H atoms. The positions of the methyl H atoms were optimized rotationally.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
[Figure 2] Fig. 2. A view of the C—H···O and ππ interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) - x + 1, - y + 1, - z ; (ii) - x + 1 , - y + 1, - z + 1.]
1-(4-Bromophenylsulfinyl)-2-methylnaphtho[2,1-b]furan top
Crystal data top
C19H13BrO2SZ = 2
Mr = 385.26F(000) = 388
Triclinic, P1Dx = 1.643 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.7124 (1) ÅCell parameters from 7454 reflections
b = 9.4857 (1) Åθ = 2.5–28.3°
c = 10.2898 (1) ŵ = 2.78 mm1
α = 82.883 (1)°T = 173 K
β = 71.126 (1)°Block, colourless
γ = 75.672 (1)°0.33 × 0.29 × 0.27 mm
V = 778.74 (2) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer
3853 independent reflections
Radiation source: rotating anode3461 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.031
Detector resolution: 10.0 pixels mm-1θmax = 28.3°, θmin = 2.1°
ϕ and ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1212
Tmin = 0.462, Tmax = 0.517l = 1313
14577 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: difference Fourier map
wR(F2) = 0.080H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0424P)2 + 0.3115P]
where P = (Fo2 + 2Fc2)/3
3853 reflections(Δ/σ)max = 0.002
209 parametersΔρmax = 0.62 e Å3
0 restraintsΔρmin = 0.60 e Å3
Crystal data top
C19H13BrO2Sγ = 75.672 (1)°
Mr = 385.26V = 778.74 (2) Å3
Triclinic, P1Z = 2
a = 8.7124 (1) ÅMo Kα radiation
b = 9.4857 (1) ŵ = 2.78 mm1
c = 10.2898 (1) ÅT = 173 K
α = 82.883 (1)°0.33 × 0.29 × 0.27 mm
β = 71.126 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
3853 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
3461 reflections with I > 2σ(I)
Tmin = 0.462, Tmax = 0.517Rint = 0.031
14577 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.080H-atom parameters constrained
S = 1.05Δρmax = 0.62 e Å3
3853 reflectionsΔρmin = 0.60 e Å3
209 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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) top
xyzUiso*/Ueq
Br11.00152 (2)0.12635 (2)0.16983 (2)0.03951 (8)
S10.35059 (5)0.29100 (5)0.20858 (4)0.02531 (10)
O10.39380 (18)0.19036 (15)0.57662 (13)0.0339 (3)
O20.34216 (16)0.44277 (15)0.14815 (14)0.0308 (3)
C10.4076 (2)0.27335 (19)0.36023 (17)0.0248 (3)
C20.5387 (2)0.31553 (19)0.39413 (17)0.0241 (3)
C30.6643 (2)0.39490 (19)0.32814 (17)0.0236 (3)
C40.6876 (2)0.46220 (19)0.19438 (17)0.0243 (3)
H40.61540.45670.14390.029*
C50.8127 (2)0.5349 (2)0.1373 (2)0.0295 (4)
H50.82650.57950.04750.035*
C60.9214 (2)0.5446 (2)0.2102 (2)0.0357 (4)
H61.00980.59330.16890.043*
C70.8993 (3)0.4836 (2)0.3402 (2)0.0357 (4)
H70.97210.49180.38920.043*
C80.7706 (2)0.4086 (2)0.40403 (19)0.0295 (4)
C90.7452 (3)0.3495 (2)0.5420 (2)0.0357 (4)
H90.81650.36110.59100.043*
C100.6220 (3)0.2772 (2)0.60542 (19)0.0353 (4)
H100.60450.23920.69760.042*
C110.5225 (2)0.2618 (2)0.52789 (18)0.0293 (4)
C120.3248 (2)0.2003 (2)0.47280 (19)0.0301 (4)
C130.1834 (3)0.1278 (3)0.5032 (2)0.0419 (5)
H13A0.13090.15410.42990.063*
H13B0.10170.15940.59120.063*
H13C0.22430.02190.50870.063*
C140.5374 (2)0.17880 (19)0.10434 (17)0.0234 (3)
C150.5817 (3)0.0335 (2)0.14588 (19)0.0313 (4)
H150.51730.00310.23080.038*
C160.7191 (3)0.0578 (2)0.0640 (2)0.0333 (4)
H160.74970.15740.09160.040*
C170.8116 (2)0.0017 (2)0.05890 (19)0.0283 (4)
C180.7683 (2)0.1426 (2)0.10104 (18)0.0286 (4)
H180.83350.17920.18550.034*
C190.6289 (2)0.2341 (2)0.01936 (17)0.0259 (3)
H190.59700.33320.04800.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.03626 (13)0.03675 (14)0.04460 (13)0.00190 (9)0.01114 (9)0.01442 (9)
S10.0229 (2)0.0272 (2)0.0268 (2)0.00701 (17)0.01025 (16)0.00538 (16)
O10.0371 (7)0.0337 (8)0.0231 (6)0.0025 (6)0.0056 (5)0.0069 (5)
O20.0278 (6)0.0283 (7)0.0344 (7)0.0035 (5)0.0129 (5)0.0092 (5)
C10.0234 (8)0.0242 (9)0.0231 (8)0.0015 (7)0.0060 (6)0.0016 (6)
C20.0258 (8)0.0217 (8)0.0212 (7)0.0024 (6)0.0078 (6)0.0021 (6)
C30.0239 (8)0.0210 (8)0.0239 (8)0.0013 (6)0.0079 (6)0.0047 (6)
C40.0247 (8)0.0214 (8)0.0261 (8)0.0015 (7)0.0089 (6)0.0025 (6)
C50.0287 (9)0.0254 (9)0.0324 (9)0.0046 (7)0.0069 (7)0.0034 (7)
C60.0304 (9)0.0314 (11)0.0481 (11)0.0095 (8)0.0112 (8)0.0084 (8)
C70.0330 (10)0.0342 (11)0.0458 (11)0.0035 (8)0.0194 (9)0.0117 (8)
C80.0307 (9)0.0272 (10)0.0318 (9)0.0023 (7)0.0147 (7)0.0092 (7)
C90.0418 (11)0.0343 (11)0.0346 (10)0.0050 (8)0.0240 (9)0.0080 (8)
C100.0452 (11)0.0334 (11)0.0232 (8)0.0054 (9)0.0152 (8)0.0022 (7)
C110.0313 (9)0.0271 (9)0.0240 (8)0.0020 (7)0.0077 (7)0.0001 (7)
C120.0284 (9)0.0273 (10)0.0272 (8)0.0004 (7)0.0040 (7)0.0026 (7)
C130.0353 (11)0.0409 (12)0.0419 (11)0.0124 (9)0.0024 (9)0.0092 (9)
C140.0276 (8)0.0228 (9)0.0229 (8)0.0076 (7)0.0114 (6)0.0020 (6)
C150.0411 (10)0.0259 (10)0.0266 (8)0.0120 (8)0.0092 (8)0.0058 (7)
C160.0460 (11)0.0202 (9)0.0339 (9)0.0064 (8)0.0143 (8)0.0017 (7)
C170.0314 (9)0.0274 (9)0.0300 (9)0.0063 (7)0.0132 (7)0.0061 (7)
C180.0326 (9)0.0314 (10)0.0236 (8)0.0103 (8)0.0096 (7)0.0018 (7)
C190.0325 (9)0.0229 (9)0.0245 (8)0.0073 (7)0.0130 (7)0.0044 (6)
Geometric parameters (Å, º) top
Br1—C171.8932 (19)C8—C91.428 (3)
S1—O21.4899 (13)C9—C101.360 (3)
S1—C11.7621 (17)C9—H90.9500
S1—C141.7966 (19)C10—C111.395 (3)
O1—C121.369 (2)C10—H100.9500
O1—C111.378 (2)C12—C131.486 (3)
C1—C121.360 (2)C13—H13A0.9800
C1—C21.451 (2)C13—H13B0.9800
C2—C111.382 (2)C13—H13C0.9800
C2—C31.424 (2)C14—C191.384 (2)
C3—C41.417 (2)C14—C151.389 (3)
C3—C81.427 (2)C15—C161.381 (3)
C4—C51.366 (2)C15—H150.9500
C4—H40.9500C16—C171.385 (3)
C5—C61.411 (3)C16—H160.9500
C5—H50.9500C17—C181.380 (3)
C6—C71.363 (3)C18—C191.390 (3)
C6—H60.9500C18—H180.9500
C7—C81.413 (3)C19—H190.9500
C7—H70.9500
O2—S1—C1110.36 (8)C9—C10—H10121.8
O2—S1—C14107.32 (8)C11—C10—H10121.8
C1—S1—C1497.62 (8)O1—C11—C2111.20 (16)
C12—O1—C11106.47 (13)O1—C11—C10123.59 (16)
C12—C1—C2107.38 (15)C2—C11—C10125.21 (18)
C12—C1—S1119.35 (14)C1—C12—O1110.59 (16)
C2—C1—S1133.18 (13)C1—C12—C13133.92 (18)
C11—C2—C3118.75 (16)O1—C12—C13115.46 (16)
C11—C2—C1104.35 (15)C12—C13—H13A109.5
C3—C2—C1136.87 (15)C12—C13—H13B109.5
C4—C3—C2124.19 (15)H13A—C13—H13B109.5
C4—C3—C8118.74 (16)C12—C13—H13C109.5
C2—C3—C8117.06 (15)H13A—C13—H13C109.5
C5—C4—C3120.72 (16)H13B—C13—H13C109.5
C5—C4—H4119.6C19—C14—C15120.80 (17)
C3—C4—H4119.6C19—C14—S1120.37 (14)
C4—C5—C6120.68 (17)C15—C14—S1118.69 (13)
C4—C5—H5119.7C16—C15—C14120.14 (17)
C6—C5—H5119.7C16—C15—H15119.9
C7—C6—C5119.72 (18)C14—C15—H15119.9
C7—C6—H6120.1C15—C16—C17118.89 (18)
C5—C6—H6120.1C15—C16—H16120.6
C6—C7—C8121.57 (17)C17—C16—H16120.6
C6—C7—H7119.2C18—C17—C16121.34 (18)
C8—C7—H7119.2C18—C17—Br1119.83 (14)
C7—C8—C3118.50 (17)C16—C17—Br1118.84 (15)
C7—C8—C9121.04 (17)C17—C18—C19119.77 (16)
C3—C8—C9120.45 (18)C17—C18—H18120.1
C10—C9—C8122.03 (18)C19—C18—H18120.1
C10—C9—H9119.0C14—C19—C18119.05 (16)
C8—C9—H9119.0C14—C19—H19120.5
C9—C10—C11116.45 (17)C18—C19—H19120.5
O2—S1—C1—C12135.73 (15)C12—O1—C11—C10178.95 (18)
C14—S1—C1—C12112.55 (16)C3—C2—C11—O1178.96 (15)
O2—S1—C1—C248.3 (2)C1—C2—C11—O10.4 (2)
C14—S1—C1—C263.40 (19)C3—C2—C11—C100.8 (3)
C12—C1—C2—C110.2 (2)C1—C2—C11—C10179.41 (18)
S1—C1—C2—C11176.07 (15)C9—C10—C11—O1179.36 (18)
C12—C1—C2—C3177.9 (2)C9—C10—C11—C20.9 (3)
S1—C1—C2—C35.8 (3)C2—C1—C12—O10.8 (2)
C11—C2—C3—C4176.38 (17)S1—C1—C12—O1176.13 (13)
C1—C2—C3—C41.6 (3)C2—C1—C12—C13178.5 (2)
C11—C2—C3—C82.4 (3)S1—C1—C12—C131.6 (3)
C1—C2—C3—C8179.6 (2)C11—O1—C12—C11.0 (2)
C2—C3—C4—C5179.11 (17)C11—O1—C12—C13179.19 (18)
C8—C3—C4—C52.1 (3)O2—S1—C14—C199.52 (16)
C3—C4—C5—C60.0 (3)C1—S1—C14—C19123.69 (14)
C4—C5—C6—C71.5 (3)O2—S1—C14—C15174.66 (14)
C5—C6—C7—C80.9 (3)C1—S1—C14—C1560.49 (15)
C6—C7—C8—C31.2 (3)C19—C14—C15—C160.4 (3)
C6—C7—C8—C9177.87 (19)S1—C14—C15—C16176.20 (15)
C4—C3—C8—C72.7 (3)C14—C15—C16—C170.4 (3)
C2—C3—C8—C7178.44 (17)C15—C16—C17—C180.5 (3)
C4—C3—C8—C9176.43 (17)C15—C16—C17—Br1179.21 (14)
C2—C3—C8—C92.5 (3)C16—C17—C18—C190.2 (3)
C7—C8—C9—C10179.9 (2)Br1—C17—C18—C19179.89 (13)
C3—C8—C9—C100.8 (3)C15—C14—C19—C181.1 (3)
C8—C9—C10—C110.9 (3)S1—C14—C19—C18176.81 (13)
C12—O1—C11—C20.9 (2)C17—C18—C19—C141.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C19—H19···O2i0.952.353.221 (2)152
Symmetry code: (i) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC19H13BrO2S
Mr385.26
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)8.7124 (1), 9.4857 (1), 10.2898 (1)
α, β, γ (°)82.883 (1), 71.126 (1), 75.672 (1)
V3)778.74 (2)
Z2
Radiation typeMo Kα
µ (mm1)2.78
Crystal size (mm)0.33 × 0.29 × 0.27
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.462, 0.517
No. of measured, independent and
observed [I > 2σ(I)] reflections
14577, 3853, 3461
Rint0.031
(sin θ/λ)max1)0.666
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.080, 1.05
No. of reflections3853
No. of parameters209
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.62, 0.60

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C19—H19···O2i0.952.353.221 (2)152.2
Symmetry code: (i) x+1, y+1, z.
 

References

First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.
First citationBruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationChoi, H. D., Seo, P. J. & Lee, U. (2012). Acta Cryst. E68, o549.  Web of Science CSD CrossRef IUCr Journals
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