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

Arunakumar, D.B.; Nivedita, R.D.; Sreenivasa, S.; Madan Kumar, S.; Lokanath, N.K.; Suchetan, P.A.

doi:10.1107/S1600536813033102

organic compounds

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Volume 70| Part 1| January 2014| Page o40

https://doi.org/10.1107/S1600536813033102

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

D. B. Arunakumar,^a R. Desai Nivedita,^a S. Sreenivasa,^a S. Madan Kumar,^b N. K. Lokanath ^b and P. A. Suchetan ^c ^*

^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.

CCDC reference: 975717

Related literature

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

Crystal data

C₁₀H₉NO₂
M_r = 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 ) T_min = 0.772, T_max = 0.839
2478 measured reflections
1333 independent reflections
1199 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.146
S = 1.07
1333 reflections
120 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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); 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.

Supporting information

CCDC reference: 975717

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S1600536813033102/hb7169sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813033102/hb7169Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813033102/hb7169Isup3.cml

checkCIF report

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.

Structure description 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).

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

	Fig. 1. Molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level.
	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

C₁₀H₉NO₂	Prism
M_r = 175.18	D_x = 1.378 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 473 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54178 Å
a = 9.5727 (12) Å	Cell parameters from 1331 reflections
b = 4.7303 (8) Å	θ = 4.7–64.6°
c = 18.756 (2) Å	µ = 0.80 mm⁻¹
β = 96.178 (6)°	T = 293 K
V = 844.4 (2) Å³	Prism, colourless
Z = 4	0.35 × 0.27 × 0.22 mm
F(000) = 368

Data collection top

Bruker APEXII CCD diffractometer	1333 independent reflections
Radiation source: fine-focus sealed tube	1199 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
φ and ω scans	θ_max = 64.6°, θ_min = 4.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→10
T_min = 0.772, T_max = 0.839	k = −5→2
2478 measured reflections	l = −20→21

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.1028P)² + 0.2023P] where P = (F_o² + 2F_c²)/3
1333 reflections	(Δ/σ)_max < 0.001
120 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₀H₉NO₂	V = 844.4 (2) Å³
M_r = 175.18	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 9.5727 (12) Å	µ = 0.80 mm⁻¹
b = 4.7303 (8) Å	T = 293 K
c = 18.756 (2) Å	0.35 × 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)
T_min = 0.772, T_max = 0.839	R_int = 0.019
2478 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.07	Δρ_max = 0.22 e Å⁻³
1333 reflections	Δρ_min = −0.40 e Å⁻³
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

	x	y	z	U_iso*/U_eq
C1	1.04643 (18)	0.3538 (4)	0.41182 (10)	0.0348 (5)
C2	1.06183 (18)	0.5553 (4)	0.35964 (10)	0.0354 (5)
C3	1.1963 (2)	0.6670 (5)	0.35443 (12)	0.0458 (6)
H3	1.2109	0.8023	0.3200	0.055*
C4	1.3051 (2)	0.5706 (5)	0.40151 (12)	0.0464 (6)
H4	1.3950	0.6408	0.3985	0.056*
C5	1.2848 (2)	0.3703 (5)	0.45370 (12)	0.0473 (6)
H5	1.3612	0.3125	0.4851	0.057*
C6	1.1547 (2)	0.2556 (5)	0.46007 (12)	0.0464 (6)
H6	1.1406	0.1206	0.4946	0.056*
C7	0.92452 (19)	0.5946 (4)	0.32240 (10)	0.0377 (5)
H7	0.9003	0.7176	0.2844	0.045*
C8	0.83702 (18)	0.4191 (4)	0.35294 (9)	0.0318 (5)
C9	0.68805 (17)	0.3508 (4)	0.34237 (9)	0.0312 (5)
C10	0.63408 (19)	0.1283 (5)	0.38897 (11)	0.0402 (5)
H10A	0.5356	0.0996	0.3752	0.060*
H10B	0.6482	0.1879	0.4381	0.060*
H10C	0.6838	−0.0453	0.3835	0.060*
N1	0.59615 (15)	0.4690 (3)	0.29671 (8)	0.0351 (4)
O1	0.90954 (12)	0.2666 (3)	0.40845 (7)	0.0375 (4)
O2	0.65313 (13)	0.6771 (3)	0.25538 (7)	0.0417 (4)
H2	0.5897	0.7764	0.2361	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0229 (9)	0.0405 (11)	0.0394 (10)	−0.0014 (7)	−0.0031 (7)	−0.0013 (8)
C2	0.0281 (9)	0.0408 (11)	0.0362 (9)	−0.0008 (7)	−0.0014 (7)	−0.0015 (8)
C3	0.0338 (10)	0.0546 (14)	0.0491 (12)	−0.0073 (9)	0.0052 (8)	0.0056 (10)
C4	0.0256 (9)	0.0568 (14)	0.0560 (12)	−0.0056 (8)	0.0009 (8)	−0.0058 (10)
C5	0.0294 (10)	0.0572 (14)	0.0526 (12)	0.0018 (9)	−0.0084 (8)	−0.0023 (10)
C6	0.0316 (11)	0.0553 (14)	0.0497 (12)	−0.0009 (9)	−0.0075 (8)	0.0113 (10)
C7	0.0312 (10)	0.0441 (11)	0.0361 (9)	−0.0003 (8)	−0.0036 (7)	0.0064 (8)
C8	0.0275 (9)	0.0341 (10)	0.0318 (9)	0.0022 (7)	−0.0059 (7)	−0.0009 (7)
C9	0.0255 (9)	0.0332 (10)	0.0332 (9)	0.0006 (7)	−0.0041 (7)	−0.0045 (7)
C10	0.0317 (10)	0.0418 (12)	0.0455 (11)	−0.0051 (8)	−0.0034 (8)	0.0028 (8)
N1	0.0286 (8)	0.0373 (10)	0.0376 (8)	−0.0004 (6)	−0.0043 (6)	−0.0024 (6)
O1	0.0254 (7)	0.0431 (9)	0.0417 (8)	−0.0027 (5)	−0.0068 (5)	0.0092 (6)
O2	0.0326 (7)	0.0471 (9)	0.0432 (8)	0.0027 (6)	−0.0059 (6)	0.0107 (6)

Geometric parameters (Å, º) top

C1—O1	1.369 (2)	C7—C8	1.350 (3)
C1—C6	1.381 (3)	C7—H7	0.9300
C1—C2	1.385 (3)	C8—O1	1.390 (2)
C2—C3	1.404 (3)	C8—C9	1.455 (2)
C2—C7	1.433 (3)	C9—N1	1.288 (2)
C3—C4	1.370 (3)	C9—C10	1.495 (3)
C3—H3	0.9300	C10—H10A	0.9600
C4—C5	1.391 (3)	C10—H10B	0.9600
C4—H4	0.9300	C10—H10C	0.9600
C5—C6	1.375 (3)	N1—O2	1.400 (2)
C5—H5	0.9300	O2—H2	0.8200
C6—H6	0.9300

O1—C1—C6	125.18 (18)	C8—C7—C2	106.98 (17)
O1—C1—C2	110.42 (15)	C8—C7—H7	126.5
C6—C1—C2	124.40 (17)	C2—C7—H7	126.5
C1—C2—C3	118.42 (17)	C7—C8—O1	110.76 (15)
C1—C2—C7	105.77 (16)	C7—C8—C9	136.28 (17)
C3—C2—C7	135.81 (19)	O1—C8—C9	112.96 (15)
C4—C3—C2	118.0 (2)	N1—C9—C8	125.71 (18)
C4—C3—H3	121.0	N1—C9—C10	116.12 (15)
C2—C3—H3	121.0	C8—C9—C10	118.16 (15)
C3—C4—C5	121.75 (18)	C9—C10—H10A	109.5
C3—C4—H4	119.1	C9—C10—H10B	109.5
C5—C4—H4	119.1	H10A—C10—H10B	109.5
C6—C5—C4	121.77 (19)	C9—C10—H10C	109.5
C6—C5—H5	119.1	H10A—C10—H10C	109.5
C4—C5—H5	119.1	H10B—C10—H10C	109.5
C5—C6—C1	115.7 (2)	C9—N1—O2	113.26 (14)
C5—C6—H6	122.2	C1—O1—C8	106.06 (14)
C1—C6—H6	122.2	N1—O2—H2	109.5

O1—C1—C2—C3	−179.18 (17)	C2—C7—C8—O1	0.1 (2)
C6—C1—C2—C3	0.6 (3)	C2—C7—C8—C9	−179.9 (2)
O1—C1—C2—C7	0.5 (2)	C7—C8—C9—N1	−3.0 (4)
C6—C1—C2—C7	−179.7 (2)	O1—C8—C9—N1	177.02 (16)
C1—C2—C3—C4	−0.1 (3)	C7—C8—C9—C10	178.2 (2)
C7—C2—C3—C4	−179.7 (2)	O1—C8—C9—C10	−1.7 (2)
C2—C3—C4—C5	−0.6 (3)	C8—C9—N1—O2	0.6 (3)
C3—C4—C5—C6	1.0 (4)	C10—C9—N1—O2	179.33 (15)
C4—C5—C6—C1	−0.5 (3)	C6—C1—O1—C8	179.8 (2)
O1—C1—C6—C5	179.47 (19)	C2—C1—O1—C8	−0.4 (2)
C2—C1—C6—C5	−0.3 (3)	C7—C8—O1—C1	0.2 (2)
C1—C2—C7—C8	−0.3 (2)	C9—C8—O1—C1	−179.84 (14)
C3—C2—C7—C8	179.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1ⁱ	0.82	2.03	2.838 (2)	166

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1ⁱ	0.82	2.03	2.838 (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

Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Demirayak, S., Ucucu, U., Benkli, K., Gundogdu, K. N. & Karaburun, A. C. (2002). II Farmaco, 57, 609–612. Web of Science CrossRef CAS Google Scholar
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. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Mehnaz, K., Shakya, A. K. & Jawaid, T. (2011). IJMPS, 3, 1–15. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar