organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

2-[(3-Oxo-1-benzo­furan-6-yl)­­oxy]aceto­nitrile

aResearch Center for Synthesis and Catalysis, Department of Chemistry, University of Johannesburg (APK Campus), PO Box 524, Auckland Park, Johannesburg, 2006, South Africa
*Correspondence e-mail: zhphasha@uj.ac.za

(Received 31 October 2012; accepted 26 November 2012; online 12 December 2012)

The mol­ecule of the title compound, C11H8O3, is essentially planar [r.m.s. deviation = 0.025 (2) Å]. In the crystal, mol­ecules are stacked along [110] but no short ππ contacts are observed. Weak C—H⋯O inter­actions link the mol­ecules into chains along [101].

Related literature

For background to the development of hybrid drug candidates against tuberculosis, malaria and cancer, see: Morphy et al. (2004[Morphy, R., Kay, C. & Rankovic, Z. (2004). Drug Discov. Today, 9, 641-651.]). For the synthesis of the title compound, see: Hoogendoorn et al. (2011[Hoogendoorn, S., Blom, A. E. M., Willems, L. I., Van der Marel, G. A. & Overkleeft, H. S. (2011). Org. Lett. 13, 5656-5659.]).

[Scheme 1]

Experimental

Crystal data
  • C11H8O3

  • Mr = 188.17

  • Monoclinic, C 2/c

  • a = 16.8785 (5) Å

  • b = 5.4202 (2) Å

  • c = 19.6107 (6) Å

  • β = 91.469 (2)°

  • V = 1793.49 (10) Å3

  • Z = 8

  • Cu Kα radiation

  • μ = 0.85 mm−1

  • T = 100 K

  • 0.19 × 0.15 × 0.11 mm

Data collection
  • Bruker APEX DUO 4K CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.855, Tmax = 0.912

  • 10685 measured reflections

  • 1545 independent reflections

  • 1451 reflections with I > 2σ(I)

  • Rint = 0.026

Refinement
  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 0.076

  • S = 1.04

  • 1545 reflections

  • 127 parameters

  • H-atom parameters constrained

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.13 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C11—H11⋯O1i 0.95 2.24 3.1676 (15) 165
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2011[Bruker (2011). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). SADABS, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2008[Bruker (2008). SADABS, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Supporting information


Comment top

As a continuation of our progress in the development of hybrid drug candidates against tuberculosis, malaria and cancer (Morphy et al., 2004), the title compound was identified as a promising starting material. The compound was synthesized by reaction of 6–Hydroxy–benzofuran–3–one with propargyl bromide at comparatively low temperature in the presence of potassium carbonate (Hoogendoorn et al., 2011). To confirm the effect of temperature on the reaction, herein we report the single-crystal structure of the title Compound.

The molecular structure of the compound is shown in Figure 1. The molecule is essentially planar (r.m.s. deviation = 0.025 (2) Å). In the crystal the molecules are linked by infinite one-dimensional C–H···O hydrogen bonding into chains that propagate in the [101] direction (Table 1, Figure 2).

Related literature top

For background to the development of hybrid drug candidates against tuberculosis, malaria and cancer, see: Morphy et al. (2004). For the synthesis of the title compound, see: Hoogendoorn et al. (2011).

Experimental top

A solution of 6–Hydroxy–benzofuran–3–one (1 g, 6.66 mm) in dry acetone was treated with potassium carbonate (1.3 g, 9.32 mm). The reaction mixture was heated at a temperature of 40 – 50 °C for about 30 minutes and then propargyl bromide (1.6 ml, 14.65 mm) was added to it. The combined solution was stirred for about 2.5 h and concentrated under vacuum. The residue was diluted with water and extracted three times with ethyl acetate. The combined organic layer was washed with brine and water and dried over anhydrous magnesium sulfate. After that filtered and the filtrate solid product was recrystalized from ethyl acetate and hexane to afford 80% of the target compound as yellow crystal.

Analytical data: m.p: 112 – 114 oC; 1H NMR (CDCl3, 400 MHZ): d 7.56 (d, 1H), 6.69 – 6.64 (m, 2H), 4.74 (s, 2H), 4.60 (s, 2H), 2.57(s, 1H); 13C NMR (CDCl3, 400 MHZ): d 197.6, 176.1, 165.8, 125.2, 115.0, 111.9, 97.7, 75.2, 56.2.

Refinement top

All hydrogen atoms were positioned in geometrically idealized positions with C—H = 0.99 Å (methylene), 0.95 Å (aromatic and acetylenic). All hydrogen atoms were allowed to ride on their parent atoms with Uiso(H) = 1.2Ueq. The highest residual electron density of 0.18 e.Å-3 is 0.66 Å from C3.

Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top
[Figure 1] Fig. 1. Crystal structure of the title compound with labeling and displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. A portion of the crystal packing viewed approximately down the b axis. Dotted lines show intermolecular C–H···O interactions.
2-[(3-Oxo-1-benzofuran-6-yl)oxy]acetonitrile top
Crystal data top
C11H8O3F(000) = 784
Mr = 188.17Dx = 1.394 Mg m3
Monoclinic, C2/cCu Kα radiation, λ = 1.54178 Å
Hall symbol: -C 2ycCell parameters from 6173 reflections
a = 16.8785 (5) Åθ = 6.8–65.7°
b = 5.4202 (2) ŵ = 0.85 mm1
c = 19.6107 (6) ÅT = 100 K
β = 91.469 (2)°Cube, yellow
V = 1793.49 (10) Å30.19 × 0.15 × 0.11 mm
Z = 8
Data collection top
Bruker APEX DUO 4K CCD
diffractometer
1545 independent reflections
Incoatec Quazar Multilayer Mirror monochromator1451 reflections with I > 2σ(I)
Detector resolution: 8.4 pixels mm-1Rint = 0.026
ϕ and ω scansθmax = 66.2°, θmin = 6.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1918
Tmin = 0.855, Tmax = 0.912k = 66
10685 measured reflectionsl = 2223
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: inferred from neighbouring sites
wR(F2) = 0.076H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0326P)2 + 1.2605P]
where P = (Fo2 + 2Fc2)/3
1545 reflections(Δ/σ)max < 0.001
127 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.13 e Å3
Crystal data top
C11H8O3V = 1793.49 (10) Å3
Mr = 188.17Z = 8
Monoclinic, C2/cCu Kα radiation
a = 16.8785 (5) ŵ = 0.85 mm1
b = 5.4202 (2) ÅT = 100 K
c = 19.6107 (6) Å0.19 × 0.15 × 0.11 mm
β = 91.469 (2)°
Data collection top
Bruker APEX DUO 4K CCD
diffractometer
1545 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
1451 reflections with I > 2σ(I)
Tmin = 0.855, Tmax = 0.912Rint = 0.026
10685 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.076H-atom parameters constrained
S = 1.04Δρmax = 0.18 e Å3
1545 reflectionsΔρmin = 0.13 e Å3
127 parameters
Special details top

Experimental. The intensity data was collected on a Bruker Apex DUO 4 K CCD diffractometer using an exposure time of 5 s/frame. A total of 2405 frames were collected with a frame width of 1° covering up to θ = 66.21° with 98.0% completeness accomplished.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.33402 (7)0.0134 (2)0.16647 (6)0.0301 (3)
H1A0.39080.01770.15820.036*
H1B0.330.13660.20350.036*
C20.29260 (7)0.2247 (2)0.18581 (6)0.0275 (3)
C30.22985 (7)0.2558 (2)0.13478 (6)0.0258 (3)
C40.23445 (6)0.0603 (2)0.08957 (6)0.0252 (3)
C50.18383 (6)0.0313 (2)0.03363 (6)0.0256 (3)
H50.1880.10420.00320.031*
C60.12641 (6)0.2130 (2)0.02471 (6)0.0253 (3)
C70.12021 (7)0.4147 (2)0.06963 (6)0.0275 (3)
H70.08020.53540.06180.033*
C80.17159 (7)0.4373 (2)0.12444 (6)0.0277 (3)
H8A0.16780.57310.15480.033*
C90.07331 (7)0.0050 (2)0.07344 (6)0.0281 (3)
H9A0.06230.14960.04850.034*
H9B0.12630.0090.09360.034*
C100.01328 (7)0.0443 (2)0.12691 (6)0.0295 (3)
C110.03534 (7)0.0700 (2)0.17094 (6)0.0340 (3)
H110.07440.09060.20630.041*
O10.31189 (5)0.35618 (16)0.23405 (4)0.0328 (2)
O20.29422 (5)0.10199 (15)0.10488 (4)0.0296 (2)
O30.07151 (5)0.21196 (15)0.02749 (4)0.0289 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0269 (6)0.0336 (7)0.0295 (6)0.0015 (5)0.0041 (5)0.0012 (5)
C20.0270 (6)0.0289 (6)0.0265 (6)0.0038 (5)0.0012 (5)0.0022 (5)
C30.0264 (6)0.0253 (6)0.0257 (6)0.0028 (5)0.0015 (4)0.0019 (5)
C40.0226 (5)0.0245 (6)0.0285 (6)0.0000 (4)0.0032 (4)0.0043 (5)
C50.0262 (6)0.0246 (6)0.0261 (6)0.0008 (5)0.0029 (4)0.0001 (5)
C60.0243 (6)0.0269 (6)0.0248 (6)0.0023 (5)0.0010 (4)0.0040 (5)
C70.0288 (6)0.0236 (6)0.0303 (6)0.0022 (5)0.0001 (5)0.0025 (5)
C80.0313 (6)0.0232 (6)0.0288 (6)0.0003 (5)0.0018 (5)0.0001 (5)
C90.0276 (6)0.0295 (6)0.0273 (6)0.0010 (5)0.0016 (5)0.0016 (5)
C100.0279 (6)0.0311 (6)0.0296 (6)0.0003 (5)0.0047 (5)0.0010 (5)
C110.0297 (6)0.0418 (7)0.0304 (6)0.0012 (5)0.0018 (5)0.0021 (5)
O10.0324 (5)0.0349 (5)0.0307 (5)0.0012 (4)0.0048 (3)0.0026 (4)
O20.0273 (4)0.0297 (5)0.0316 (4)0.0052 (3)0.0036 (3)0.0019 (3)
O30.0288 (4)0.0298 (4)0.0278 (4)0.0034 (3)0.0046 (3)0.0026 (3)
Geometric parameters (Å, º) top
C1—O21.4489 (14)C6—O31.3631 (13)
C1—C21.5206 (17)C6—C71.4095 (16)
C1—H1A0.99C7—C81.3691 (17)
C1—H1B0.99C7—H70.95
C2—O11.2220 (14)C8—H8A0.95
C2—C31.4481 (16)C9—O31.4396 (14)
C3—C41.3851 (16)C9—C101.4551 (16)
C3—C81.4021 (17)C9—H9A0.99
C4—O21.3661 (14)C9—H9B0.99
C4—C51.3822 (16)C10—C111.1840 (17)
C5—C61.3896 (16)C11—H110.95
C5—H50.95
O2—C1—C2106.42 (9)O3—C6—C7114.37 (10)
O2—C1—H1A110.4C5—C6—C7122.25 (10)
C2—C1—H1A110.4C8—C7—C6120.30 (11)
O2—C1—H1B110.4C8—C7—H7119.8
C2—C1—H1B110.4C6—C7—H7119.8
H1A—C1—H1B108.6C7—C8—C3118.58 (11)
O1—C2—C3129.99 (11)C7—C8—H8A120.7
O1—C2—C1124.96 (11)C3—C8—H8A120.7
C3—C2—C1105.04 (9)O3—C9—C10108.15 (9)
C4—C3—C8119.66 (10)O3—C9—H9A110.1
C4—C3—C2107.53 (10)C10—C9—H9A110.1
C8—C3—C2132.81 (11)O3—C9—H9B110.1
O2—C4—C5122.62 (10)C10—C9—H9B110.1
O2—C4—C3113.91 (10)H9A—C9—H9B108.4
C5—C4—C3123.47 (11)C11—C10—C9178.27 (13)
C4—C5—C6115.74 (11)C10—C11—H11180
C4—C5—H5122.1C4—O2—C1107.09 (9)
C6—C5—H5122.1C6—O3—C9116.64 (9)
O3—C6—C5123.37 (10)
O2—C1—C2—O1177.45 (10)C4—C5—C6—C70.20 (16)
O2—C1—C2—C31.34 (12)O3—C6—C7—C8179.74 (10)
O1—C2—C3—C4177.78 (12)C5—C6—C7—C80.07 (17)
C1—C2—C3—C40.93 (12)C6—C7—C8—C30.23 (17)
O1—C2—C3—C81.2 (2)C4—C3—C8—C70.40 (16)
C1—C2—C3—C8179.91 (12)C2—C3—C8—C7179.28 (11)
C8—C3—C4—O2179.30 (10)C5—C4—O2—C1179.70 (10)
C2—C3—C4—O20.16 (13)C3—C4—O2—C10.73 (12)
C8—C3—C4—C50.27 (17)C2—C1—O2—C41.26 (12)
C2—C3—C4—C5179.41 (10)C5—C6—O3—C92.07 (15)
O2—C4—C5—C6179.56 (10)C7—C6—O3—C9177.74 (9)
C3—C4—C5—C60.03 (16)C10—C9—O3—C6177.25 (9)
C4—C5—C6—O3179.59 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···O1i0.952.243.1676 (15)165
Symmetry code: (i) x1/2, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC11H8O3
Mr188.17
Crystal system, space groupMonoclinic, C2/c
Temperature (K)100
a, b, c (Å)16.8785 (5), 5.4202 (2), 19.6107 (6)
β (°) 91.469 (2)
V3)1793.49 (10)
Z8
Radiation typeCu Kα
µ (mm1)0.85
Crystal size (mm)0.19 × 0.15 × 0.11
Data collection
DiffractometerBruker APEX DUO 4K CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.855, 0.912
No. of measured, independent and
observed [I > 2σ(I)] reflections
10685, 1545, 1451
Rint0.026
(sin θ/λ)max1)0.593
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.076, 1.04
No. of reflections1545
No. of parameters127
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.13

Computer programs: APEX2 (Bruker, 2011), SAINT (Bruker, 2008), SAINT and XPREP (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···O1i0.952.243.1676 (15)164.6
Symmetry code: (i) x1/2, y+1/2, z1/2.
 

Acknowledgements

Support by the research funds of the University of Johannesburg is gratefully acknowledged.

References

First citationBruker (2008). SADABS, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationBruker (2011). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationHoogendoorn, S., Blom, A. E. M., Willems, L. I., Van der Marel, G. A. & Overkleeft, H. S. (2011). Org. Lett. 13, 5656–5659.  Web of Science CrossRef CAS PubMed
First citationMorphy, R., Kay, C. & Rankovic, Z. (2004). Drug Discov. Today, 9, 641–651.  Web of Science CrossRef PubMed CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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COMMUNICATIONS
ISSN: 2056-9890
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