Crystal structure of 1-(5-bromo-1-benzo-furan-2-yl)ethanone oxime.

The title compound, C10H8BrNO2, is almost planar (r.m.s. deviation for the non-H atoms = 0.031 Å) and the conformation across the C=N bond is trans. Further, the O atom of the benzo-furan ring is syn to the N atom of the oxime group. In the crystal, inversion dimers linked by pairs of O-H⋯N hydrogen bonds generate R 2 (2)(6) loops. Very weak aromatic π-π stacking inter-actions [centroid-centroid separations = 3.9100 (12) and 3.9447 (12) Å] are also observed.

Related literature

For the various biological activities of the benzo­furan moiety, see: Rida et al. (2006 ▸); Manna et al. (2010 ▸); Patil et al. (2010 ▸); Patel et al. (2006 ▸). For the anti­fungal activity of (benzo­furan-2-yl) ken class="Chemical">oximes, see: Demirayak et al. (2002 ▸). For related structures, see: Aruna Kumar et al. (2014 ▸).

Experimental

Crystal data

C10H8BrNO2

M = 254.08

Monoclinic,

a = 5.9548 (6) Å

b = 9.4897 (10) Å

c = 17.2906 (19) Å

β = 96.943 (6)°

V = 969.91 (18) Å3

Z = 4

Mo Kα radiation

μ = 4.21 mm−1

T = 296 K

0.32 × 0.25 × 0.21 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.294, T max = 0.413

10152 measured reflections

2766 independent reflections

1937 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.096

S = 1.01

2766 reflections

129 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAIn class="Chemical">NT-Plus (Bruker, 2009 ▸); data reduction: SAINT-Plus; 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. DOI: 10.1107/S205698901501751X/hb7505sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901501751X/hb7505Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S205698901501751X/hb7505Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S205698901501751X/hb7505fig1.tif

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

Click here for additional data file.

. DOI: 10.1107/S205698901501751X/hb7505fig2.tif

Crystal packing of the title compound displaying O—H⋯N and π–π inter­actions.

CCDC reference: 1425831

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

C10H8BrNO2	F(000) = 504
Mr = 254.08	Prism
Monoclinic, P21/n	Dx = 1.740 Mg m−3
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 5.9548 (6) Å	Cell parameters from 125 reflections
b = 9.4897 (10) Å	θ = 3.5–29.9°
c = 17.2906 (19) Å	µ = 4.21 mm−1
β = 96.943 (6)°	T = 296 K
V = 969.91 (18) Å3	Prism, colourless
Z = 4	0.32 × 0.25 × 0.21 mm

Bruker APEXII diffractometer	1937 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Graphite monochromator	θmax = 29.9°, θmin = 3.5°
phi and φ scans	h = −8→7
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→10
Tmin = 0.294, Tmax = 0.413	l = −18→24
10152 measured reflections	1 standard reflections every 2 reflections
2766 independent reflections	intensity decay: 0.5%

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0563P)2 + 0.0157P] where P = (Fo2 + 2Fc2)/3
2766 reflections	(Δ/σ)max = 0.001
129 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.33 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
C8	0.5278 (3)	−0.2686 (2)	−0.00305 (11)	0.0391 (4)
C1	0.3056 (3)	0.0480 (2)	0.16815 (12)	0.0447 (5)
C2	0.5215 (3)	0.0179 (2)	0.20434 (11)	0.0492 (5)
H2	0.5745	0.0626	0.2509	0.059*
C3	0.6569 (3)	−0.0767 (2)	0.17233 (12)	0.0492 (5)
H3	0.8014	−0.0979	0.1961	0.059*
C4	0.5691 (3)	−0.1394 (2)	0.10298 (11)	0.0390 (4)
C5	0.3543 (3)	−0.1120 (2)	0.06601 (11)	0.0403 (4)
C6	0.2169 (3)	−0.0159 (2)	0.09927 (12)	0.0470 (5)
H6	0.0714	0.0043	0.0761	0.056*
C7	0.3324 (3)	−0.1982 (2)	−0.00278 (12)	0.0437 (5)
H7	0.2065	−0.2041	−0.0401	0.052*
C9	0.6021 (3)	−0.3724 (2)	−0.05598 (11)	0.0412 (4)
C10	0.4500 (4)	−0.4102 (3)	−0.12802 (12)	0.0513 (5)
H10A	0.4955	−0.3594	−0.1716	0.077*
H10B	0.2969	−0.3859	−0.1215	0.077*
H10C	0.4598	−0.5096	−0.1373	0.077*
N1	0.7969 (3)	−0.42793 (19)	−0.03532 (10)	0.0445 (4)
O1	0.6789 (2)	−0.23533 (16)	0.06169 (8)	0.0440 (3)
O2	0.8582 (2)	−0.52765 (17)	−0.08799 (9)	0.0548 (4)
H2A	0.9720	−0.5695	−0.0688	0.082*
Br1	0.13019 (4)	0.18428 (3)	0.214769 (13)	0.05936 (13)

	U11	U22	U33	U12	U13	U23
C8	0.0409 (10)	0.0392 (10)	0.0356 (10)	−0.0021 (8)	−0.0023 (7)	0.0055 (8)
C1	0.0505 (11)	0.0403 (11)	0.0447 (11)	0.0004 (8)	0.0111 (8)	0.0024 (9)
C2	0.0551 (12)	0.0525 (13)	0.0388 (11)	−0.0044 (10)	0.0009 (8)	−0.0040 (9)
C3	0.0452 (10)	0.0586 (14)	0.0412 (11)	−0.0014 (9)	−0.0058 (8)	−0.0012 (10)
C4	0.0362 (9)	0.0410 (11)	0.0394 (10)	−0.0003 (8)	0.0032 (7)	0.0031 (8)
C5	0.0401 (9)	0.0391 (11)	0.0405 (10)	−0.0005 (8)	0.0002 (7)	0.0062 (8)
C6	0.0442 (10)	0.0492 (12)	0.0464 (12)	0.0043 (9)	0.0010 (8)	0.0035 (9)
C7	0.0391 (10)	0.0498 (13)	0.0403 (11)	0.0035 (8)	−0.0037 (8)	−0.0002 (9)
C9	0.0429 (10)	0.0416 (11)	0.0384 (10)	−0.0034 (8)	0.0028 (8)	0.0051 (9)
C10	0.0520 (11)	0.0552 (14)	0.0444 (12)	0.0022 (10)	−0.0030 (9)	−0.0011 (10)
N1	0.0447 (9)	0.0462 (10)	0.0420 (9)	0.0057 (7)	0.0028 (7)	−0.0024 (7)
O1	0.0379 (7)	0.0496 (8)	0.0420 (7)	0.0041 (6)	−0.0052 (5)	−0.0014 (6)
O2	0.0562 (9)	0.0591 (10)	0.0493 (8)	0.0142 (7)	0.0066 (6)	−0.0069 (7)
Br1	0.0661 (2)	0.05433 (19)	0.06028 (19)	0.00532 (9)	0.01851 (12)	−0.00638 (10)

C8—C7	1.343 (3)	C5—C6	1.394 (3)
C8—O1	1.385 (2)	C5—C7	1.437 (3)
C8—C9	1.449 (3)	C6—H6	0.9300
C1—C6	1.383 (3)	C7—H7	0.9300
C1—C2	1.390 (3)	C9—N1	1.285 (3)
C1—Br1	1.901 (2)	C9—C10	1.493 (3)
C2—C3	1.367 (3)	C10—H10A	0.9600
C2—H2	0.9300	C10—H10B	0.9600
C3—C4	1.383 (3)	C10—H10C	0.9600
C3—H3	0.9300	N1—O2	1.392 (2)
C4—O1	1.371 (2)	O2—H2A	0.8200
C4—C5	1.384 (2)
C7—C8—O1	111.24 (18)	C1—C6—C5	117.40 (17)
C7—C8—C9	132.16 (16)	C1—C6—H6	121.3
O1—C8—C9	116.56 (17)	C5—C6—H6	121.3
C6—C1—C2	122.23 (19)	C8—C7—C5	107.11 (16)
C6—C1—Br1	119.44 (15)	C8—C7—H7	126.4
C2—C1—Br1	118.33 (15)	C5—C7—H7	126.4
C3—C2—C1	120.75 (18)	N1—C9—C8	115.94 (16)
C3—C2—H2	119.6	N1—C9—C10	124.7 (2)
C1—C2—H2	119.6	C8—C9—C10	119.31 (17)
C2—C3—C4	117.00 (18)	C9—C10—H10A	109.5
C2—C3—H3	121.5	C9—C10—H10B	109.5
C4—C3—H3	121.5	H10A—C10—H10B	109.5
O1—C4—C3	125.70 (16)	C9—C10—H10C	109.5
O1—C4—C5	110.89 (16)	H10A—C10—H10C	109.5
C3—C4—C5	123.4 (2)	H10B—C10—H10C	109.5
C4—C5—C6	119.22 (18)	C9—N1—O2	113.35 (16)
C4—C5—C7	105.18 (17)	C4—O1—C8	105.58 (15)
C6—C5—C7	135.61 (16)	N1—O2—H2A	109.5
C6—C1—C2—C3	0.5 (3)	C9—C8—C7—C5	178.2 (2)
Br1—C1—C2—C3	−178.43 (16)	C4—C5—C7—C8	−0.3 (2)
C1—C2—C3—C4	0.2 (3)	C6—C5—C7—C8	179.5 (2)
C2—C3—C4—O1	179.3 (2)	C7—C8—C9—N1	−174.5 (2)
C2—C3—C4—C5	−0.6 (3)	O1—C8—C9—N1	3.3 (3)
O1—C4—C5—C6	−179.65 (18)	C7—C8—C9—C10	3.9 (4)
C3—C4—C5—C6	0.3 (3)	O1—C8—C9—C10	−178.38 (19)
O1—C4—C5—C7	0.2 (2)	C8—C9—N1—O2	179.41 (17)
C3—C4—C5—C7	−179.9 (2)	C10—C9—N1—O2	1.1 (3)
C2—C1—C6—C5	−0.9 (3)	C3—C4—O1—C8	−179.9 (2)
Br1—C1—C6—C5	178.09 (15)	C5—C4—O1—C8	0.0 (2)
C4—C5—C6—C1	0.4 (3)	C7—C8—O1—C4	−0.3 (2)
C7—C5—C6—C1	−179.3 (2)	C9—C8—O1—C4	−178.48 (16)
O1—C8—C7—C5	0.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N1i	0.82	2.13	2.808 (2)	140

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O2H2AN1i	0.82	2.13	2.808(2)	140

Symmetry code: (i) .