Literature DB >> 21583634

7-Bromo-1-methyl-sulfinyl-2-phenyl-naphtho[2,1-b]furan.

Hong Dae Choi, Pil Ja Seo, Byeng Wha Son, Uk Lee.   

Abstract

In the title compound, C(19)H(13)BrO(2)S, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the naphthofuran unit. The phenyl ring is rotated out of the naphthofuran plane, making a dihedral angle of 42.2 (1)°. The crystal structure is stabilized by two inter-molecular C-H⋯π inter-actions, and by non-classical inter-molecular C-H⋯O and C-H⋯Br hydrogen bonds.

Entities:  

Year:  2009        PMID： 21583634      PMCID： PMC2977132          DOI： 10.1107/S1600536809028165

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


Related literature

For the crystal structures of similar 2-phenyl­naphtho[2,1-b]furan derivatives, see: Choi et al. (2009a ▶,b ▶). For details of the biological and pharmacological activity of naphthofuran compounds, see: Goel & Dixit (2004 ▶); Hagiwara et al. (1999 ▶); Piloto et al. (2005 ▶).

Experimental

Crystal data

C19H13BrO2S M = 385.26 Monoclinic, a = 6.0007 (4) Å b = 22.699 (2) Å c = 11.2151 (8) Å β = 91.267 (1)° V = 1527.2 (2) Å3 Z = 4 Mo Kα radiation μ = 2.84 mm−1 T = 273 K 0.25 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ▶) T min = 0.538, T max = 0.765 13412 measured reflections 3476 independent reflections 2280 reflections with I > 2σ(I) R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.039 wR(F 2) = 0.091 S = 1.09 3476 reflections 209 parameters H-atom parameters constrained Δρmax = 0.56 e Å−3 Δρmin = −0.49 e Å−3 Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536809028165/rk2156sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028165/rk2156Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C19H13BrO2SF(000) = 776
Mr = 385.26Dx = 1.676 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3117 reflections
a = 6.0007 (4) Åθ = 2.6–27.3°
b = 22.699 (2) ŵ = 2.84 mm−1
c = 11.2151 (8) ÅT = 273 K
β = 91.267 (1)°Block, colourless
V = 1527.2 (2) Å30.25 × 0.12 × 0.10 mm
Z = 4
Bruker SMART CCD diffractometer3476 independent reflections
Radiation source: fine-focus sealed tube2280 reflections with I > 2σ(I)
graphiteRint = 0.056
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 1.8°
φ and ω scansh = −7→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)k = −29→29
Tmin = 0.538, Tmax = 0.765l = −14→14
13412 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)] = 0.039Hydrogen site location: difference Fourier map
wR(F2) = 0.091H-atom parameters constrained
S = 1.09w = 1/[σ2(Fo2) + (0.0234P)2 + 2.3626P] where P = (Fo2 + 2Fc2)/3
3476 reflections(Δ/σ)max = 0.002
209 parametersΔρmax = 0.56 e Å−3
0 restraintsΔρmin = −0.49 e Å−3
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Br1.04085 (7)0.614541 (18)1.06514 (4)0.03289 (13)
S0.04668 (16)0.71912 (4)0.66608 (8)0.0231 (2)
O1−0.0349 (4)0.54760 (10)0.6267 (2)0.0208 (5)
O20.0802 (4)0.74221 (11)0.7894 (2)0.0316 (7)
C10.0664 (6)0.64129 (15)0.6686 (3)0.0191 (7)
C20.2146 (6)0.60190 (15)0.7355 (3)0.0195 (8)
C30.4067 (6)0.60777 (15)0.8130 (3)0.0194 (7)
C40.4927 (6)0.66186 (16)0.8559 (3)0.0234 (8)
H40.42100.69670.83430.028*
C50.6794 (6)0.66431 (17)0.9287 (3)0.0255 (9)
H50.73430.70030.95600.031*
C60.7857 (6)0.61148 (17)0.9610 (3)0.0243 (8)
C70.7101 (6)0.55824 (16)0.9228 (3)0.0237 (8)
H70.78540.52410.94550.028*
C80.5162 (6)0.55461 (16)0.8484 (3)0.0210 (8)
C90.4331 (6)0.49849 (16)0.8115 (3)0.0230 (8)
H90.50840.46460.83570.028*
C100.2455 (6)0.49362 (15)0.7415 (3)0.0233 (8)
H100.18830.45710.71930.028*
C110.1437 (6)0.54571 (15)0.7050 (3)0.0196 (8)
C12−0.0772 (6)0.60640 (15)0.6050 (3)0.0199 (8)
C13−0.2527 (6)0.61732 (16)0.5143 (3)0.0206 (7)
C14−0.4437 (6)0.58201 (15)0.5112 (3)0.0226 (8)
H14−0.45950.55210.56710.027*
C15−0.6085 (6)0.59122 (17)0.4259 (3)0.0273 (9)
H15−0.73490.56750.42410.033*
C16−0.5855 (7)0.63605 (17)0.3422 (3)0.0286 (9)
H16−0.69850.64300.28590.034*
C17−0.3945 (7)0.67033 (16)0.3429 (3)0.0284 (9)
H17−0.37850.69980.28610.034*
C18−0.2277 (6)0.66085 (15)0.4275 (3)0.0229 (8)
H18−0.09850.68350.42670.028*
C190.2979 (7)0.73401 (16)0.5874 (3)0.0284 (9)
H19A0.33140.77530.59210.043*
H19B0.27790.72280.50530.043*
H19C0.41870.71190.62260.043*
U11U22U33U12U13U23
Br0.0306 (2)0.0375 (2)0.0302 (2)−0.0047 (2)−0.00788 (15)0.0030 (2)
S0.0258 (5)0.0177 (5)0.0260 (5)0.0017 (4)0.0018 (4)−0.0027 (4)
O10.0258 (14)0.0156 (12)0.0210 (13)−0.0033 (10)0.0000 (11)0.0003 (10)
O20.0401 (17)0.0287 (15)0.0262 (15)0.0017 (13)0.0037 (12)−0.0113 (12)
C10.0228 (19)0.0155 (17)0.0191 (18)−0.0026 (15)0.0037 (14)−0.0009 (14)
C20.0244 (19)0.0190 (19)0.0154 (17)−0.0003 (15)0.0047 (14)0.0001 (14)
C30.0215 (18)0.0202 (18)0.0168 (17)−0.0005 (15)0.0030 (14)0.0011 (15)
C40.028 (2)0.0196 (19)0.022 (2)−0.0003 (16)0.0027 (16)0.0015 (15)
C50.028 (2)0.026 (2)0.022 (2)−0.0066 (17)0.0003 (16)−0.0022 (16)
C60.0241 (19)0.031 (2)0.0177 (17)−0.0044 (18)−0.0007 (14)0.0000 (17)
C70.027 (2)0.025 (2)0.0191 (18)0.0043 (17)0.0010 (15)0.0022 (16)
C80.026 (2)0.0229 (19)0.0148 (17)0.0037 (16)0.0037 (15)0.0005 (15)
C90.030 (2)0.0195 (19)0.0193 (19)0.0040 (16)0.0005 (16)0.0020 (15)
C100.036 (2)0.0162 (18)0.0184 (19)−0.0054 (16)0.0037 (16)−0.0006 (15)
C110.0215 (19)0.0195 (18)0.0178 (18)−0.0020 (15)0.0018 (15)−0.0009 (14)
C120.0227 (19)0.0163 (19)0.0210 (18)−0.0006 (15)0.0060 (14)−0.0019 (14)
C130.0211 (18)0.0220 (18)0.0188 (17)0.0031 (16)0.0041 (14)−0.0055 (16)
C140.026 (2)0.0186 (19)0.0236 (19)0.0014 (16)0.0055 (16)−0.0032 (15)
C150.021 (2)0.032 (2)0.029 (2)0.0007 (16)−0.0001 (16)−0.0096 (17)
C160.032 (2)0.030 (2)0.024 (2)0.0073 (18)−0.0055 (17)−0.0074 (17)
C170.040 (2)0.023 (2)0.022 (2)0.0049 (18)0.0018 (18)0.0003 (16)
C180.023 (2)0.0210 (19)0.025 (2)−0.0013 (16)0.0005 (16)−0.0022 (15)
C190.037 (2)0.022 (2)0.026 (2)−0.0037 (18)0.0034 (17)−0.0001 (16)
Br—C61.906 (3)C9—C101.362 (5)
S—O21.489 (3)C9—H90.9300
S—C11.771 (3)C10—C111.389 (5)
S—C191.796 (4)C10—H100.9300
O1—C111.371 (4)C12—C131.469 (5)
O1—C121.379 (4)C13—C181.398 (5)
C1—C121.360 (5)C13—C141.398 (5)
C1—C21.457 (5)C14—C151.377 (5)
C2—C111.385 (5)C14—H140.9300
C2—C31.434 (5)C15—C161.393 (5)
C3—C41.412 (5)C15—H150.9300
C3—C81.426 (5)C16—C171.385 (5)
C4—C51.373 (5)C16—H160.9300
C4—H40.9300C17—C181.381 (5)
C5—C61.402 (5)C17—H170.9300
C5—H50.9300C18—H180.9300
C6—C71.357 (5)C19—H19A0.9600
C7—C81.420 (5)C19—H19B0.9600
C7—H70.9300C19—H19C0.9600
C8—C91.426 (5)
O2—S—C1109.20 (16)C9—C10—H10121.5
O2—S—C19107.03 (17)C11—C10—H10121.5
C1—S—C1997.99 (17)O1—C11—C2111.2 (3)
C11—O1—C12106.3 (3)O1—C11—C10123.2 (3)
C12—C1—C2106.6 (3)C2—C11—C10125.5 (3)
C12—C1—S122.1 (3)C1—C12—O1111.1 (3)
C2—C1—S131.3 (3)C1—C12—C13134.5 (3)
C11—C2—C3118.3 (3)O1—C12—C13114.3 (3)
C11—C2—C1104.9 (3)C18—C13—C14119.2 (3)
C3—C2—C1136.7 (3)C18—C13—C12121.0 (3)
C4—C3—C8118.6 (3)C14—C13—C12119.7 (3)
C4—C3—C2124.8 (3)C15—C14—C13120.4 (3)
C8—C3—C2116.7 (3)C15—C14—H14119.8
C5—C4—C3121.7 (3)C13—C14—H14119.8
C5—C4—H4119.2C14—C15—C16119.9 (4)
C3—C4—H4119.2C14—C15—H15120.0
C4—C5—C6118.7 (3)C16—C15—H15120.0
C4—C5—H5120.7C17—C16—C15120.1 (4)
C6—C5—H5120.7C17—C16—H16120.0
C7—C6—C5122.2 (3)C15—C16—H16120.0
C7—C6—Br119.0 (3)C18—C17—C16120.2 (4)
C5—C6—Br118.8 (3)C18—C17—H17119.9
C6—C7—C8120.1 (3)C16—C17—H17119.9
C6—C7—H7120.0C17—C18—C13120.1 (3)
C8—C7—H7120.0C17—C18—H18119.9
C7—C8—C9119.9 (3)C13—C18—H18119.9
C7—C8—C3118.8 (3)S—C19—H19A109.5
C9—C8—C3121.3 (3)S—C19—H19B109.5
C10—C9—C8121.2 (3)H19A—C19—H19B109.5
C10—C9—H9119.4S—C19—H19C109.5
C8—C9—H9119.4H19A—C19—H19C109.5
C9—C10—C11117.0 (3)H19B—C19—H19C109.5
O2—S—C1—C12137.3 (3)C8—C9—C10—C111.9 (5)
C19—S—C1—C12−111.5 (3)C12—O1—C11—C21.0 (4)
O2—S—C1—C2−39.4 (4)C12—O1—C11—C10−175.3 (3)
C19—S—C1—C271.8 (4)C3—C2—C11—O1−177.3 (3)
C12—C1—C2—C11−0.1 (4)C1—C2—C11—O1−0.6 (4)
S—C1—C2—C11177.1 (3)C3—C2—C11—C10−1.1 (5)
C12—C1—C2—C3175.8 (4)C1—C2—C11—C10175.6 (3)
S—C1—C2—C3−7.1 (6)C9—C10—C11—O1174.5 (3)
C11—C2—C3—C4−177.2 (3)C9—C10—C11—C2−1.3 (5)
C1—C2—C3—C47.4 (7)C2—C1—C12—O10.7 (4)
C11—C2—C3—C82.7 (5)S—C1—C12—O1−176.8 (2)
C1—C2—C3—C8−172.7 (4)C2—C1—C12—C13−174.3 (4)
C8—C3—C4—C51.0 (5)S—C1—C12—C138.3 (6)
C2—C3—C4—C5−179.1 (3)C11—O1—C12—C1−1.0 (4)
C3—C4—C5—C6−0.2 (6)C11—O1—C12—C13175.0 (3)
C4—C5—C6—C70.0 (6)C1—C12—C13—C1837.7 (6)
C4—C5—C6—Br−178.5 (3)O1—C12—C13—C18−137.1 (3)
C5—C6—C7—C8−0.5 (5)C1—C12—C13—C14−145.2 (4)
Br—C6—C7—C8178.0 (3)O1—C12—C13—C1440.0 (4)
C6—C7—C8—C9−178.0 (3)C18—C13—C14—C15−2.0 (5)
C6—C7—C8—C31.3 (5)C12—C13—C14—C15−179.2 (3)
C4—C3—C8—C7−1.5 (5)C13—C14—C15—C16−0.2 (5)
C2—C3—C8—C7178.6 (3)C14—C15—C16—C171.7 (6)
C4—C3—C8—C9177.8 (3)C15—C16—C17—C18−1.0 (6)
C2—C3—C8—C9−2.1 (5)C16—C17—C18—C13−1.2 (6)
C7—C8—C9—C10179.0 (3)C14—C13—C18—C172.7 (5)
C3—C8—C9—C10−0.3 (5)C12—C13—C18—C17179.9 (3)
D—H···AD—HH···AD···AD—H···A
C14—H14···Cg1i0.932.703.377 (4)131
C19—H19B···Cg2ii0.962.993.497 (4)114
C18—H18···O2iii0.932.543.283 (4)137
C16—H16···Briv0.932.973.823 (4)153
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C14—H14⋯Cg1i0.932.703.377 (4)131
C19—H19B⋯Cg2ii0.962.993.497 (4)114
C18—H18⋯O2iii0.932.543.283 (4)137
C16—H16⋯Briv0.932.973.823 (4)153

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 and Cg2 are the centroids of the C2/C3/C8–C11 benzene and C13–C18 benzene rings, respectively.

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Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  7-Bromo-2-phenyl-1-(phenyl-sulfin-yl)naphtho[2,1-b]furan benzene hemisolvate.

Authors:  Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-07-11

3.  2-Phenyl-1-(phenyl-sulfin-yl)naphtho[2,1-b]furan.

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Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-05-29
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1.  7-Bromo-2-(4-fluoro-phen-yl)-1-(methyl-sulfin-yl)naphtho[2,1-b]furan.

Authors:  Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-04-02

2.  7-Bromo-1-(4-chloro-phenyl-sulfan-yl)-2-phenyl-naphtho[2,1-b]furan.

Authors:  Hong Dae Choi; Pil Ja Seo; Byung Ki Kim; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-12-16

3.  7-Bromo-2-(4-methyl-phen-yl)-1-(methyl-sulfin-yl)naphtho-[2,1-b]furan.

Authors:  Hong Dae Choi; Pil Ja Seo; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-06-22
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