Literature DB >> 22606178

1-(4-Bromo-phenyl-sulfin-yl)-2-methyl-naphtho-[2,1-b]furan.

Hong Dae Choi, Pil Ja Seo, Uk Lee.   

Abstract

In the title compound, C(19)H(13)BrO(2)S, the 4-bromo-phenyl ring makes a dihedral angle of 83.75 (4)° with the mean plane of the naphtho-furan fragment [r.m.s. deviation = 0.024 (2) Å]. In the crystal, mol-ecules are linked via pairs of C-H⋯O hydrogen bonds, forming inversion dimers. These dimers are connected by weak π-π inter-actions between the central naphtho-furan benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.483 (2) Å, inter-planar distance = 3.416 (2) Å and slippage = 0.680 (2) Å].

Entities:  

Year:  2012        PMID： 22606178      PMCID： PMC3344175          DOI： 10.1107/S1600536812012603

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

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

Experimental

Crystal data

C19H13BrO2S M = 385.26 Triclinic, 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 ▶) T min = 0.462, T max = 0.517 14577 measured reflections 3853 independent reflections 3461 reflections with I > 2σ(I) R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.030 wR(F 2) = 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 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536812012603/sj5222sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012603/sj5222Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812012603/sj5222Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C19H13BrO2SZ = 2
Mr = 385.26F(000) = 388
Triclinic, P1Dx = 1.643 Mg m−3
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 mm−1
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
Bruker SMART APEXII CCD diffractometer3853 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 = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)k = −12→12
Tmin = 0.462, Tmax = 0.517l = −13→13
14577 measured reflections
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 = 1.05w = 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 Å−3
0 restraintsΔρmin = −0.60 e Å−3
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.
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)
H150.5173−0.00310.23080.038*
C160.7191 (3)−0.0578 (2)0.0640 (2)0.0333 (4)
H160.7497−0.15740.09160.040*
C170.8116 (2)−0.0017 (2)−0.05890 (19)0.0283 (4)
C180.7683 (2)0.1426 (2)−0.10104 (18)0.0286 (4)
H180.83350.1792−0.18550.034*
C190.6289 (2)0.2341 (2)−0.01936 (17)0.0259 (3)
H190.59700.3332−0.04800.031*
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)
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—C12−112.55 (16)C3—C2—C11—O1178.96 (15)
O2—S1—C1—C2−48.3 (2)C1—C2—C11—O10.4 (2)
C14—S1—C1—C263.40 (19)C3—C2—C11—C10−0.8 (3)
C12—C1—C2—C110.2 (2)C1—C2—C11—C10−179.41 (18)
S1—C1—C2—C11−176.07 (15)C9—C10—C11—O1179.36 (18)
C12—C1—C2—C3−177.9 (2)C9—C10—C11—C2−0.9 (3)
S1—C1—C2—C35.8 (3)C2—C1—C12—O1−0.8 (2)
C11—C2—C3—C4−176.38 (17)S1—C1—C12—O1176.13 (13)
C1—C2—C3—C41.6 (3)C2—C1—C12—C13−178.5 (2)
C11—C2—C3—C82.4 (3)S1—C1—C12—C13−1.6 (3)
C1—C2—C3—C8−179.6 (2)C11—O1—C12—C11.0 (2)
C2—C3—C4—C5−179.11 (17)C11—O1—C12—C13179.19 (18)
C8—C3—C4—C52.1 (3)O2—S1—C14—C19−9.52 (16)
C3—C4—C5—C60.0 (3)C1—S1—C14—C19−123.69 (14)
C4—C5—C6—C7−1.5 (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—C9−177.87 (19)S1—C14—C15—C16176.20 (15)
C4—C3—C8—C7−2.7 (3)C14—C15—C16—C170.4 (3)
C2—C3—C8—C7178.44 (17)C15—C16—C17—C18−0.5 (3)
C4—C3—C8—C9176.43 (17)C15—C16—C17—Br1179.21 (14)
C2—C3—C8—C9−2.5 (3)C16—C17—C18—C19−0.2 (3)
C7—C8—C9—C10179.9 (2)Br1—C17—C18—C19−179.89 (13)
C3—C8—C9—C100.8 (3)C15—C14—C19—C18−1.1 (3)
C8—C9—C10—C110.9 (3)S1—C14—C19—C18−176.81 (13)
C12—O1—C11—C2−0.9 (2)C17—C18—C19—C141.0 (3)
D—H···AD—HH···AD···AD—H···A
C19—H19···O2i0.952.353.221 (2)152
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C19—H19⋯O2i0.952.353.221 (2)152

Symmetry code: (i) .

  2 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  2-Methyl-1-(4-methyl-phenyl-sulfinyl)naphtho-[2,1-b]furan.

Authors:  Hong Dae Choi; Pil Ja Seo; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-01-31
  2 in total

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