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Acta Crystallogr E Crystallogr Commun

Acta Cryst. E

Acta Crystallographica Section E: Crystallographic Communications

2056-9890

International Union of Crystallography

26594472

4647387

hb7505

10.1107/S205698901501751X

ACSECI

S205698901501751X

Data Reports

Crystal structure of 1-(5-bromo-1-benzofuran-2-yl)ethanone oxime

C₁₀H₈BrNO₂

Krishnaswamy

aKrishna Murthy

aNivedita Desai

aSuchetan

P. A.

a‡Aruna Kumar

D. B.

a*‡aDept. of Studies and Research in Chemistry, University College of Science, Tumkur University, Tumkur 572103, India

Correspondence e-mail: nirmaldb@rediffmail.com‡

These authors contributed equally.

01102015

2692015

71Pt 10

e151000

o773o77414920151892015

2015

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

A full version of this article is available from Crystallography Journals Online.

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 benzofuran 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 interactions [centroid–centroid separations = 3.9100 (12) and 3.9447 (12) Å] are also observed.

crystal structure1-(5-bromobenzofuran-2-yl) ethanone oximehydrogen bondingπ–π stacking interactions

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) keoximes, see: Demirayak et al. (2002 ▸). For related structures, see: Aruna Kumar et al. (2014 ▸).

Experimental Crystal data

C₁₀H₈BrNO₂

M _r = 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

Δρ_max = 0.29 e Å⁻³

Δρ_min = −0.33 e Å⁻³

Data collection: <italic>APEX2</italic> (Bruker, 2009<xref ref-type="bibr" rid="bb2"> ▸</xref>); cell refinement: <italic>SAINT-Plus</italic> (Bruker, 2009<xref ref-type="bibr" rid="bb2"> ▸</xref>); data reduction: <italic>SAINT-Plus</italic>; program(s) used to solve structure: <italic>SHELXS97</italic> (Sheldrick, 2008<xref ref-type="bibr" rid="bb9"> ▸</xref>); program(s) used to refine structure: <italic>SHELXL97</italic> (Sheldrick, 2008<xref ref-type="bibr" rid="bb9"> ▸</xref>); molecular graphics: <italic>Mercury</italic> (Macrae <italic>et al.</italic>, 2008<xref ref-type="bibr" rid="bb4"> ▸</xref>); software used to prepare material for publication: <italic>SHELXL97</italic>.</sec></sec><sec sec-type="supplementary-material"><title>Supplementary Material

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

Supporting information for this paper is available from the IUCr electronic archives (Reference: HB7505).

The authors are thankful to the Department of Science and Technology, New Delhi, Government of India for providing financial assistance under the DST FAST TRACK [SR/FT/CS-81/2010 (G)] scheme, and also thank Tumkur University for the administrative support to carry out the project.

supplementary crystallographic informationS1. Chemical context

The literature indicates that compounds having benzofuran nucleus possesses versatile pharmacological activities like anifungal, antiarrythmic, uricisuric, vasodilator and antimigraine agent (Rida et al., 2006; Manna et al., 2010; Patil et al., 2010; Patel et al., 2006). Further, (Benzofuran-2-yl) keoxime derivatives are known to show good antifungal activities (Demirayak et al., 2002). In view of the above and in continuation of our efforts to study the crystal structures of benzofuran moities (Aruna Kumar et al., 2014), the title compound was synthesized and its crystal structure was determined.

S2. Structural commentary

The title compound (I), 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 in (I) (Figure 1). In contrast to this, the conformation across the C=N bond is syn in (1Z)-1-(1-Benzofuran-2-yl)ethanone oxime (II) (Aruna Kumar et al., 2014). Further, the O atom of the benzofuran ring is trans to the CH₃ group in the side chain of (I), where as, in (II) (Aruna Kumar et al., 2014), it is syn. The torsions in the side chain of (I) have values: O1—C8—C9—N1 = 3.3 (3)^o, C8—C9—N1—O2 = 179.41 (17)^o and C7—C8—C9—C10 = 3.9 (4)^o. The corresponding torsions in (II) have values 177.02 (16)^o, 0.6 (3)^o and 178.2 (2)^o respectively (Aruna Kumar et al., 2014).

S3. Supramolecular features

The crystal structure features strong O2—H2A···N1 hydrogen bonds leading into R₂²(6) dimers, and these dimers are further interconnected via two π···π interactions, namely cg1···cg1 and cg1···cg2 (where cg1 is the centroid of the furan ring C4/C5/C7/C8/O1 and cg2 is the centroid of the aryl ring C1—C6) (Figure 2, Table 2), the centroid-centroid separations being 3.9447 (12) Å and 3.9100 (12) Å respectively.

S4. Synthesis and crystallization

5-bromo-2-acetylbenzofuran (1 g, 0.0062 mmol), hydroxylamine hydrochloride (0.65 g, 0.0093 mmol) and anhydrous K₂CO₃ (1.29 g, 0.0093 mmol) were taken in EtOH: H₂O (3:1, 10 mL) and refluxed for 3 h. After the completion of the reaction, the reaction mixture was poured into ice cold water. The separated white solid was filtered, washed with water and dried. It was recrystallized from EtOH.

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

S5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. 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 parametersfor all H atoms were set to 1.2 times Ueq(Caromatic) and 1.5 times Ueq(Cmethyl, O).

FiguresFig. 1.

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

Fig. 2.

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

Crystal data

C₁₀H₈BrNO₂	F(000) = 504
M_r = 254.08	Prism
Monoclinic, P2₁/n	D_x = 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

Data collection

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

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0563P)² + 0.0157P] where P = (F_o² + 2F_c²)/3
2766 reflections	(Δ/σ)_max = 0.001
129 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.33 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 (Å2)

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å2)

	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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

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

Symmetry code: (i) −x+2, −y−1, −z.

References

Arunakumar, D. B., Nivedita, R. D., Sreenivasa, S., Madan Kumar, S., Lokanath, N. K. & Suchetan, P. A. (2014). Acta Cryst. E70, o40.

Bruker (2009). APEX2, SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.

Demirayak, S., Ucucu, U., Benkli, K., Gundogdu-Karaburun, N. & Karaburun, A. C. (2002). II Farmaco, 57, 609–612.

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.

Manna, K. U. & Agrawal, Y. K. (2010). Eur. J. Med. Chem. 45, 3831–3839.

Patel, H. J., Sarra, J., Caruso, F., Rossi, M., Doshi, U. & Stephani, R. A. (2006). Bioorg. Med. Chem. Lett. 16, 4644–4647.

Patil, S. L., Bhalgat, C. M., Burli, S. & Chithale, S. K. (2010). J. Chem. Sci Appl. 1, 42–49.

Rida, S. M., El-Hawash, S. A. M., Fahmy, H. T., Hazzaa, A. A. & El-Meligy, M. M. M. (2006). Arch. Pharm. Res. 29, 826–833.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Table 1Hydrogen-bond geometry (, )

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

Symmetry code: (i) .