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

Abstract

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 ▶). For the anti­fungal activity of (benzo­furan-2-yl) keoximes, see: Demirayak et al. (2002 ▶).

Experimental  

Crystal data  

• C₁₀H₉NO₂

• M _r = 175.18

• Monoclinic,

• a = 9.5727 (12) Å

• b = 4.7303 (8) Å

• c = 18.756 (2) Å

• β = 96.178 (6)°

• V = 844.4 (2) ų

• 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[F ² > 2σ(F ²)] = 0.062

• wR(F ²) = 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

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.

Supplementary Material

Additional supporting information: crystallographic information; 3D view; checkCIF report

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) .

supplementary crystallographic information

1. Comment

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.

2. Experimental

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.

3. Refinement

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 U_eq (C_aromatic) and 1.5 times U_eq (C_methyl, O)..

Figures

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.

Crystal data

C10H9NO2	Prism
Mr = 175.18	Dx = 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

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

Refinement

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(Fo2) + (0.1028P)2 + 0.2023P] where P = (Fo2 + 2Fc2)/3
1333 reflections	(Δ/σ)max < 0.001
120 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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)

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)

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.