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ISSN: 2056-9890
Volume 71| Part 10| October 2015| Pages o773-o774

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

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aDept. of Studies and Research in Chemistry, University College of Science, Tumkur University, Tumkur 572103, India
*Correspondence e-mail: nirmaldb@rediffmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 14 September 2015; accepted 18 September 2015; online 26 September 2015)

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 R22(6) loops. Very weak aromatic ππ stacking inter­actions [centroid–centroid separations = 3.9100 (12) and 3.9447 (12) Å] are also observed.

1. Related literature

For the various biological activities of the benzo­furan moiety, see: Rida et al. (2006[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.]); Manna et al. (2010[Manna, K. U. & Agrawal, Y. K. (2010). Eur. J. Med. Chem. 45, 3831-3839.]); Patil et al. (2010[Patil, S. L., Bhalgat, C. M., Burli, S. & Chithale, S. K. (2010). J. Chem. Sci Appl. 1, 42-49.]); Patel et al. (2006[Patel, H. J., Sarra, J., Caruso, F., Rossi, M., Doshi, U. & Stephani, R. A. (2006). Bioorg. Med. Chem. Lett. 16, 4644-4647.]). For the anti­fungal activity of (benzo­furan-2-yl) keoximes, see: Demirayak et al. (2002[Demirayak, S., Ucucu, U., Benkli, K., Gundogdu-Karaburun, N. & Karaburun, A. C. (2002). II Farmaco, 57, 609-612.]). For related structures, see: Aruna Kumar et al. (2014[Arunakumar, D. B., Nivedita, R. D., Sreenivasa, S., Madan Kumar, S., Lokanath, N. K. & Suchetan, P. A. (2014). Acta Cryst. E70, o40.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C10H8BrNO2

  • Mr = 254.08

  • Monoclinic, P 21 /n

  • 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

2.2. Data collection

  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.294, Tmax = 0.413

  • 10152 measured reflections

  • 2766 independent reflections

  • 1937 reflections with I > 2σ(I)

  • Rint = 0.023

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.033

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2A⋯N1i 0.82 2.13 2.808 (2) 140
Symmetry code: (i) -x+2, -y-1, -z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2008[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.]); software used to prepare material for publication: SHELXL97.

Supporting information


Chemical context top

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.

Structural commentary top

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).

Supra­molecular features top

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.

Synthesis and crystallization top

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.

Refinement top

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).

Related literature top

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).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus (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
[Figure 1] Fig. 1. Molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Crystal packing of the title compound displaying O—H···N and ππ interactions.
1-(5-Bromo-1-benzofuran-2-yl)ethanone oxime top
Crystal data top
C10H8BrNO2F(000) = 504
Mr = 254.08Prism
Monoclinic, P21/nDx = 1.740 Mg m3
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 5.9548 (6) ÅCell parameters from 125 reflections
b = 9.4897 (10) Åθ = 3.5–29.9°
c = 17.2906 (19) ŵ = 4.21 mm1
β = 96.943 (6)°T = 296 K
V = 969.91 (18) Å3Prism, colourless
Z = 40.32 × 0.25 × 0.21 mm
Data collection top
Bruker APEXII
diffractometer
1937 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 29.9°, θmin = 3.5°
phi and φ scansh = 87
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1310
Tmin = 0.294, Tmax = 0.413l = 1824
10152 measured reflections1 standard reflections every 2 reflections
2766 independent reflections intensity decay: 0.5%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H-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 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.33 e Å3
Crystal data top
C10H8BrNO2V = 969.91 (18) Å3
Mr = 254.08Z = 4
Monoclinic, P21/nMo Kα radiation
a = 5.9548 (6) ŵ = 4.21 mm1
b = 9.4897 (10) ÅT = 296 K
c = 17.2906 (19) Å0.32 × 0.25 × 0.21 mm
β = 96.943 (6)°
Data collection top
Bruker APEXII
diffractometer
1937 reflections with I > 2σ(I)
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
Rint = 0.023
Tmin = 0.294, Tmax = 0.4131 standard reflections every 2 reflections
10152 measured reflections intensity decay: 0.5%
2766 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.096H-atom parameters constrained
S = 1.01Δρmax = 0.29 e Å3
2766 reflectionsΔρmin = 0.33 e Å3
129 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
xyzUiso*/Ueq
C80.5278 (3)0.2686 (2)0.00305 (11)0.0391 (4)
C10.3056 (3)0.0480 (2)0.16815 (12)0.0447 (5)
C20.5215 (3)0.0179 (2)0.20434 (11)0.0492 (5)
H20.57450.06260.25090.059*
C30.6569 (3)0.0767 (2)0.17233 (12)0.0492 (5)
H30.80140.09790.19610.059*
C40.5691 (3)0.1394 (2)0.10298 (11)0.0390 (4)
C50.3543 (3)0.1120 (2)0.06601 (11)0.0403 (4)
C60.2169 (3)0.0159 (2)0.09927 (12)0.0470 (5)
H60.07140.00430.07610.056*
C70.3324 (3)0.1982 (2)0.00278 (12)0.0437 (5)
H70.20650.20410.04010.052*
C90.6021 (3)0.3724 (2)0.05598 (11)0.0412 (4)
C100.4500 (4)0.4102 (3)0.12802 (12)0.0513 (5)
H10A0.49550.35940.17160.077*
H10B0.29690.38590.12150.077*
H10C0.45980.50960.13730.077*
N10.7969 (3)0.42793 (19)0.03532 (10)0.0445 (4)
O10.6789 (2)0.23533 (16)0.06169 (8)0.0440 (3)
O20.8582 (2)0.52765 (17)0.08799 (9)0.0548 (4)
H2A0.97200.56950.06880.082*
Br10.13019 (4)0.18428 (3)0.214769 (13)0.05936 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C80.0409 (10)0.0392 (10)0.0356 (10)0.0021 (8)0.0023 (7)0.0055 (8)
C10.0505 (11)0.0403 (11)0.0447 (11)0.0004 (8)0.0111 (8)0.0024 (9)
C20.0551 (12)0.0525 (13)0.0388 (11)0.0044 (10)0.0009 (8)0.0040 (9)
C30.0452 (10)0.0586 (14)0.0412 (11)0.0014 (9)0.0058 (8)0.0012 (10)
C40.0362 (9)0.0410 (11)0.0394 (10)0.0003 (8)0.0032 (7)0.0031 (8)
C50.0401 (9)0.0391 (11)0.0405 (10)0.0005 (8)0.0002 (7)0.0062 (8)
C60.0442 (10)0.0492 (12)0.0464 (12)0.0043 (9)0.0010 (8)0.0035 (9)
C70.0391 (10)0.0498 (13)0.0403 (11)0.0035 (8)0.0037 (8)0.0002 (9)
C90.0429 (10)0.0416 (11)0.0384 (10)0.0034 (8)0.0028 (8)0.0051 (9)
C100.0520 (11)0.0552 (14)0.0444 (12)0.0022 (10)0.0030 (9)0.0011 (10)
N10.0447 (9)0.0462 (10)0.0420 (9)0.0057 (7)0.0028 (7)0.0024 (7)
O10.0379 (7)0.0496 (8)0.0420 (7)0.0041 (6)0.0052 (5)0.0014 (6)
O20.0562 (9)0.0591 (10)0.0493 (8)0.0142 (7)0.0066 (6)0.0069 (7)
Br10.0661 (2)0.05433 (19)0.06028 (19)0.00532 (9)0.01851 (12)0.00638 (10)
Geometric parameters (Å, º) top
C8—C71.343 (3)C5—C61.394 (3)
C8—O11.385 (2)C5—C71.437 (3)
C8—C91.449 (3)C6—H60.9300
C1—C61.383 (3)C7—H70.9300
C1—C21.390 (3)C9—N11.285 (3)
C1—Br11.901 (2)C9—C101.493 (3)
C2—C31.367 (3)C10—H10A0.9600
C2—H20.9300C10—H10B0.9600
C3—C41.383 (3)C10—H10C0.9600
C3—H30.9300N1—O21.392 (2)
C4—O11.371 (2)O2—H2A0.8200
C4—C51.384 (2)
C7—C8—O1111.24 (18)C1—C6—C5117.40 (17)
C7—C8—C9132.16 (16)C1—C6—H6121.3
O1—C8—C9116.56 (17)C5—C6—H6121.3
C6—C1—C2122.23 (19)C8—C7—C5107.11 (16)
C6—C1—Br1119.44 (15)C8—C7—H7126.4
C2—C1—Br1118.33 (15)C5—C7—H7126.4
C3—C2—C1120.75 (18)N1—C9—C8115.94 (16)
C3—C2—H2119.6N1—C9—C10124.7 (2)
C1—C2—H2119.6C8—C9—C10119.31 (17)
C2—C3—C4117.00 (18)C9—C10—H10A109.5
C2—C3—H3121.5C9—C10—H10B109.5
C4—C3—H3121.5H10A—C10—H10B109.5
O1—C4—C3125.70 (16)C9—C10—H10C109.5
O1—C4—C5110.89 (16)H10A—C10—H10C109.5
C3—C4—C5123.4 (2)H10B—C10—H10C109.5
C4—C5—C6119.22 (18)C9—N1—O2113.35 (16)
C4—C5—C7105.18 (17)C4—O1—C8105.58 (15)
C6—C5—C7135.61 (16)N1—O2—H2A109.5
C6—C1—C2—C30.5 (3)C9—C8—C7—C5178.2 (2)
Br1—C1—C2—C3178.43 (16)C4—C5—C7—C80.3 (2)
C1—C2—C3—C40.2 (3)C6—C5—C7—C8179.5 (2)
C2—C3—C4—O1179.3 (2)C7—C8—C9—N1174.5 (2)
C2—C3—C4—C50.6 (3)O1—C8—C9—N13.3 (3)
O1—C4—C5—C6179.65 (18)C7—C8—C9—C103.9 (4)
C3—C4—C5—C60.3 (3)O1—C8—C9—C10178.38 (19)
O1—C4—C5—C70.2 (2)C8—C9—N1—O2179.41 (17)
C3—C4—C5—C7179.9 (2)C10—C9—N1—O21.1 (3)
C2—C1—C6—C50.9 (3)C3—C4—O1—C8179.9 (2)
Br1—C1—C6—C5178.09 (15)C5—C4—O1—C80.0 (2)
C4—C5—C6—C10.4 (3)C7—C8—O1—C40.3 (2)
C7—C5—C6—C1179.3 (2)C9—C8—O1—C4178.48 (16)
O1—C8—C7—C50.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···N1i0.822.132.808 (2)140
Symmetry code: (i) x+2, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···N1i0.822.132.808 (2)140
Symmetry code: (i) x+2, y1, z.
 

Footnotes

These authors contributed equally.

Acknowledgements

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.

References

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COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 10| October 2015| Pages o773-o774
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