(1Z)-1-(1-Benzo-furan-2-yl)ethanone oxime.

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 benzo-furan ring is syn to the CH3 group in the side chain. In the crystal, mol-ecules 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 = 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) 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[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 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

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.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813033102/hb7169sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813033102/hb7169Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813033102/hb7169Isup3.cml

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

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

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 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

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.

	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*

	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)

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)

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

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) .