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

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ISSN: 2056-9890

(1Z)-1-(1-Benzo­furan-2-yl)ethanone oxime

aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India, bDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore, India, and cDepartment of Studies and Research in Chemistry, U.C.S, Tumkur University, Tumkur, Karnataka 572 103, India
*Correspondence e-mail: pasuchetan@yahoo.co.in

(Received 4 December 2013; accepted 7 December 2013; online 14 December 2013)

The title compound, C10H9NO2, is almost planar (r.m.s. deviation for the non-H atoms = 0.027 Å) and the conformation across the C=N bond is syn. Further, the O atom of the benzo­furan ring is syn to the CH3 group in the side chain. In the crystal, mol­ecules are linked into C(3) chains propagating in [010] by O—H⋯N hydrogen bonds.

Related literature

For the broad range of biological activities of the benzo­furan moiety, see: Mehnaz et al. (2011[Mehnaz, K., Shakya, A. K. & Jawaid, T. (2011). IJMPS, 3, 1-15.]). For the anti­fungal activity of (benzo­furan-2-yl) keoximes, see: Demirayak et al. (2002[Demirayak, S., Ucucu, U., Benkli, K., Gundogdu, K. N. & Karaburun, A. C. (2002). II Farmaco, 57, 609-612.]).

[Scheme 1]

Experimental

Crystal data
  • C10H9NO2

  • Mr = 175.18

  • Monoclinic, P 21 /c

  • a = 9.5727 (12) Å

  • b = 4.7303 (8) Å

  • c = 18.756 (2) Å

  • β = 96.178 (6)°

  • V = 844.4 (2) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 0.80 mm−1

  • T = 293 K

  • 0.35 × 0.27 × 0.22 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.772, Tmax = 0.839

  • 2478 measured reflections

  • 1333 independent reflections

  • 1199 reflections with I > 2σ(I)

  • Rint = 0.019

Refinement
  • R[F2 > 2σ(F2)] = 0.062

  • wR(F2) = 0.146

  • S = 1.07

  • 1333 reflections

  • 120 parameters

  • H-atom parameters constrained

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.40 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2⋯N1i 0.82 2.03 2.838 (2) 166
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus 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: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Benzofurans are bicyclic ring systems with multiple applications. The literature indicates that compounds having benzofuran nucleus possesses broad range of biological activities like anifungal, antiarrythmic, uricisuric, vasodilator and antimigraine agent (Mehnaz et al., 2011). Further, (benzofuran-2-yl) keoximes shows good antifungal activity (Demirayak et al., 2002). Keeping this thing in mind, the title compound was synthesized and its crystal structure determined.

In the title compound, C10H9NO2, the molecule is almost planar (r.m.s. deviation for the non-H atoms = 0.027 Å) and the conformation across the C=N bond is syn. Further, the oxygen atom of the benzofuran ring is syn to the CH3 group in the side chain. In the crystal structure, the molecules are linked into C(3) chains through O2—H2···N1 hydrogen bonds.

Related literature top

For the broad range of biological activities of the benzofuran moiety, see: Mehnaz et al. (2011). For the antifungal activity of (benzofuran-2-yl) keoximes, see: Demirayak et al. (2002).

Experimental top

2-Acetylbenzofuran (0.0062 mmol), hydroxyaminehydrochloride (0.0093 mmol) and anhydrous potassium carbonate (0.0093 mmol) were taken in a round bottom flask containing ethanol and water taken in the ratio 3:1. The reaction mixture was refluxed for 3 hrs·The progress of the reaction was monitored by thin layer chromatography. The reaction mixture was poured into ice cold water. The title compound separated as white solid. It was filtered, washed with water, dried and recrystallized from ethanol.

Colourless prisms were obtained from the solvent system: ethyl acetate: methanol (4:1) by recrystallisation.

Refinement top

The H atoms were positioned with idealized geometry using a riding model with C—H = 0.93–0.96 Å and O—H = 0.82 Å. The isotropic displacement parameters for all H atoms were set to 1.2 times Ueq (Caromatic) and 1.5 times Ueq (Cmethyl, O)..

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus and XPREP (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Linking of molecules into C(3) chains through O—H···N hydrogen bonds. H-atoms not involved in H-bonding are omitted for clarity purpose.
(1Z)-1-(1-Benzofuran-2-yl)ethanone oxime top
Crystal data top
C10H9NO2Prism
Mr = 175.18Dx = 1.378 Mg m3
Monoclinic, P21/cMelting point: 473 K
Hall symbol: -P 2ybcCu Kα radiation, λ = 1.54178 Å
a = 9.5727 (12) ÅCell parameters from 1331 reflections
b = 4.7303 (8) Åθ = 4.7–64.6°
c = 18.756 (2) ŵ = 0.80 mm1
β = 96.178 (6)°T = 293 K
V = 844.4 (2) Å3Prism, colourless
Z = 40.35 × 0.27 × 0.22 mm
F(000) = 368
Data collection top
Bruker APEXII CCD
diffractometer
1333 independent reflections
Radiation source: fine-focus sealed tube1199 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
ϕ and ω scansθmax = 64.6°, θmin = 4.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1110
Tmin = 0.772, Tmax = 0.839k = 52
2478 measured reflectionsl = 2021
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)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.1028P)2 + 0.2023P]
where P = (Fo2 + 2Fc2)/3
1333 reflections(Δ/σ)max < 0.001
120 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.40 e Å3
Crystal data top
C10H9NO2V = 844.4 (2) Å3
Mr = 175.18Z = 4
Monoclinic, P21/cCu Kα radiation
a = 9.5727 (12) ŵ = 0.80 mm1
b = 4.7303 (8) ÅT = 293 K
c = 18.756 (2) Å0.35 × 0.27 × 0.22 mm
β = 96.178 (6)°
Data collection top
Bruker APEXII CCD
diffractometer
1333 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
1199 reflections with I > 2σ(I)
Tmin = 0.772, Tmax = 0.839Rint = 0.019
2478 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0620 restraints
wR(F2) = 0.146H-atom parameters constrained
S = 1.07Δρmax = 0.22 e Å3
1333 reflectionsΔρmin = 0.40 e Å3
120 parameters
Special details top

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
C11.04643 (18)0.3538 (4)0.41182 (10)0.0348 (5)
C21.06183 (18)0.5553 (4)0.35964 (10)0.0354 (5)
C31.1963 (2)0.6670 (5)0.35443 (12)0.0458 (6)
H31.21090.80230.32000.055*
C41.3051 (2)0.5706 (5)0.40151 (12)0.0464 (6)
H41.39500.64080.39850.056*
C51.2848 (2)0.3703 (5)0.45370 (12)0.0473 (6)
H51.36120.31250.48510.057*
C61.1547 (2)0.2556 (5)0.46007 (12)0.0464 (6)
H61.14060.12060.49460.056*
C70.92452 (19)0.5946 (4)0.32240 (10)0.0377 (5)
H70.90030.71760.28440.045*
C80.83702 (18)0.4191 (4)0.35294 (9)0.0318 (5)
C90.68805 (17)0.3508 (4)0.34237 (9)0.0312 (5)
C100.63408 (19)0.1283 (5)0.38897 (11)0.0402 (5)
H10A0.53560.09960.37520.060*
H10B0.64820.18790.43810.060*
H10C0.68380.04530.38350.060*
N10.59615 (15)0.4690 (3)0.29671 (8)0.0351 (4)
O10.90954 (12)0.2666 (3)0.40845 (7)0.0375 (4)
O20.65313 (13)0.6771 (3)0.25538 (7)0.0417 (4)
H20.58970.77640.23610.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0229 (9)0.0405 (11)0.0394 (10)0.0014 (7)0.0031 (7)0.0013 (8)
C20.0281 (9)0.0408 (11)0.0362 (9)0.0008 (7)0.0014 (7)0.0015 (8)
C30.0338 (10)0.0546 (14)0.0491 (12)0.0073 (9)0.0052 (8)0.0056 (10)
C40.0256 (9)0.0568 (14)0.0560 (12)0.0056 (8)0.0009 (8)0.0058 (10)
C50.0294 (10)0.0572 (14)0.0526 (12)0.0018 (9)0.0084 (8)0.0023 (10)
C60.0316 (11)0.0553 (14)0.0497 (12)0.0009 (9)0.0075 (8)0.0113 (10)
C70.0312 (10)0.0441 (11)0.0361 (9)0.0003 (8)0.0036 (7)0.0064 (8)
C80.0275 (9)0.0341 (10)0.0318 (9)0.0022 (7)0.0059 (7)0.0009 (7)
C90.0255 (9)0.0332 (10)0.0332 (9)0.0006 (7)0.0041 (7)0.0045 (7)
C100.0317 (10)0.0418 (12)0.0455 (11)0.0051 (8)0.0034 (8)0.0028 (8)
N10.0286 (8)0.0373 (10)0.0376 (8)0.0004 (6)0.0043 (6)0.0024 (6)
O10.0254 (7)0.0431 (9)0.0417 (8)0.0027 (5)0.0068 (5)0.0092 (6)
O20.0326 (7)0.0471 (9)0.0432 (8)0.0027 (6)0.0059 (6)0.0107 (6)
Geometric parameters (Å, º) top
C1—O11.369 (2)C7—C81.350 (3)
C1—C61.381 (3)C7—H70.9300
C1—C21.385 (3)C8—O11.390 (2)
C2—C31.404 (3)C8—C91.455 (2)
C2—C71.433 (3)C9—N11.288 (2)
C3—C41.370 (3)C9—C101.495 (3)
C3—H30.9300C10—H10A0.9600
C4—C51.391 (3)C10—H10B0.9600
C4—H40.9300C10—H10C0.9600
C5—C61.375 (3)N1—O21.400 (2)
C5—H50.9300O2—H20.8200
C6—H60.9300
O1—C1—C6125.18 (18)C8—C7—C2106.98 (17)
O1—C1—C2110.42 (15)C8—C7—H7126.5
C6—C1—C2124.40 (17)C2—C7—H7126.5
C1—C2—C3118.42 (17)C7—C8—O1110.76 (15)
C1—C2—C7105.77 (16)C7—C8—C9136.28 (17)
C3—C2—C7135.81 (19)O1—C8—C9112.96 (15)
C4—C3—C2118.0 (2)N1—C9—C8125.71 (18)
C4—C3—H3121.0N1—C9—C10116.12 (15)
C2—C3—H3121.0C8—C9—C10118.16 (15)
C3—C4—C5121.75 (18)C9—C10—H10A109.5
C3—C4—H4119.1C9—C10—H10B109.5
C5—C4—H4119.1H10A—C10—H10B109.5
C6—C5—C4121.77 (19)C9—C10—H10C109.5
C6—C5—H5119.1H10A—C10—H10C109.5
C4—C5—H5119.1H10B—C10—H10C109.5
C5—C6—C1115.7 (2)C9—N1—O2113.26 (14)
C5—C6—H6122.2C1—O1—C8106.06 (14)
C1—C6—H6122.2N1—O2—H2109.5
O1—C1—C2—C3179.18 (17)C2—C7—C8—O10.1 (2)
C6—C1—C2—C30.6 (3)C2—C7—C8—C9179.9 (2)
O1—C1—C2—C70.5 (2)C7—C8—C9—N13.0 (4)
C6—C1—C2—C7179.7 (2)O1—C8—C9—N1177.02 (16)
C1—C2—C3—C40.1 (3)C7—C8—C9—C10178.2 (2)
C7—C2—C3—C4179.7 (2)O1—C8—C9—C101.7 (2)
C2—C3—C4—C50.6 (3)C8—C9—N1—O20.6 (3)
C3—C4—C5—C61.0 (4)C10—C9—N1—O2179.33 (15)
C4—C5—C6—C10.5 (3)C6—C1—O1—C8179.8 (2)
O1—C1—C6—C5179.47 (19)C2—C1—O1—C80.4 (2)
C2—C1—C6—C50.3 (3)C7—C8—O1—C10.2 (2)
C1—C2—C7—C80.3 (2)C9—C8—O1—C1179.84 (14)
C3—C2—C7—C8179.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N1i0.822.032.838 (2)166
Symmetry code: (i) x+1, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N1i0.822.032.838 (2)166
Symmetry code: (i) x+1, y+1/2, z+1/2.
 

Acknowledgements

The authors acknowledge the IOE X-ray diffractometer Facility, University of Mysore, Mysore, for the data collection.

References

First citationBruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationDemirayak, S., Ucucu, U., Benkli, K., Gundogdu, K. N. & Karaburun, A. C. (2002). II Farmaco, 57, 609–612.  Web of Science CrossRef CAS
First citationMacrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.  Web of Science CrossRef CAS IUCr Journals
First citationMehnaz, K., Shakya, A. K. & Jawaid, T. (2011). IJMPS, 3, 1–15.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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ISSN: 2056-9890
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