1-(5-Bromo-1-benzofuran-2-yl)ethanone

Fun, H.-K.; Quah, C.K.; Abdel-Aziz, H.A.

doi:10.1107/S160053681201985X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1682

doi:10.1107/S160053681201985X

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1-(5-Bromo-1-benzofuran-2-yl)ethanone

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah ^a § and Hatem A. Abdel-Aziz ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia
^*Correspondence e-mail: hkfun@usm.my

(Received 30 April 2012; accepted 3 May 2012; online 12 May 2012)

The title compound, C₁₀H₇BrO₂, is approximately planar (r.m.s. deviation = 0.057 Å for the 13 non-H atoms). In the crystal, molecules are linked via C—H⋯O hydrogen bonds into C(5) chains propagating in [100].

Related literature

For general background to and the biological activity of benzofuran derivatives, see: Abdel-Aziz et al. (2009 ); Abdel-Aziz & Mekawey (2009 ); Bhovi et al. (2009 ); Abdel-Wahab et al. (2009 ); Csaba et al. (2003 ); Bevinakatti & Badiger (1982 ). For reference bond lengths, see: Allen et al. (1987 ). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₀H₇BrO₂
M_r = 239.07
Orthorhombic, P b c a
a = 10.8301 (2) Å
b = 7.4630 (1) Å
c = 21.7213 (3) Å
V = 1755.62 (5) Å³
Z = 8
Mo Kα radiation
μ = 4.64 mm⁻¹
T = 100 K
0.26 × 0.19 × 0.18 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.377, T_max = 0.482
43601 measured reflections
3331 independent reflections
2689 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.058
S = 1.04
3331 reflections
119 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O2ⁱ	0.95	2.45	3.3495 (16)	158
Symmetry code: (i) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681201985X/hb6772sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201985X/hb6772Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681201985X/hb6772Isup3.cml

checkCIF report

Comment top

Benzofuran derivatives have useful biological activities, such as anticonvulsant, anti-infammatory, antitumor and antihistaminic activities. They were also found to be useful as antifungal, anthelmintic and antihyper-glycemic agents (Abdel-Aziz et al., 2009; Abdel-Aziz & Mekawey, 2009; Bhovi et al., 2009). Due to their considerable biological activities and in continuation of our interests in the chemistry and biological activities of benzofurans (Abdel-Aziz et al., 2009; Abdel-Aziz & Mekawey, 2009; Abdel-Wahab et al., 2009), the title compound (I) was synthesized to study the structure activity relationships with other benzofurans.

The title compound, Fig. 1, is approximately planar (r.m.s. deviation = 0.057 Å for the 13 non-H atoms). Bond lengths (Allen et al., 1987) and angles are within normal ranges.

In the crystal (Fig.2), molecules are linked via C7–H7A···O2 hydrogen bonds (Table 1) into chains propagating in [100].

Related literature top

For general background to and the biological activity of benzofuran derivatives, see: Abdel-Aziz et al. (2009); Abdel-Aziz & Mekawey (2009); Bhovi et al. (2009); Abdel-Wahab et al. (2009). For [what subject?], see: Csaba et al. (2003); Bevinakatti & Badiger (1982). For refererence bond lengths, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986).

Experimental top

The title compound was prepared by heating of 5-bromo-salicylaldehyde with chloroacetone in the presence of potassium hydroxide in methanol for 2 h (Csaba et al., 2003; Bevinakatti & Badiger, 1982). Colourless blocks were obtained by slow evaporation from EtOH/DMF solution.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The crystal structure of the title compound, viewed along the b axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

1-(5-Bromo-1-benzofuran-2-yl)ethanone top

Crystal data top

C₁₀H₇BrO₂	F(000) = 944
M_r = 239.07	D_x = 1.809 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9929 reflections
a = 10.8301 (2) Å	θ = 2.7–33.1°
b = 7.4630 (1) Å	µ = 4.64 mm⁻¹
c = 21.7213 (3) Å	T = 100 K
V = 1755.62 (5) Å³	Block, colourless
Z = 8	0.26 × 0.19 × 0.18 mm

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	3331 independent reflections
Radiation source: fine-focus sealed tube	2689 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ϕ and ω scans	θ_max = 33.1°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→16
T_min = 0.377, T_max = 0.482	k = −11→10
43601 measured reflections	l = −33→33

Refinement top

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.058	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0251P)² + 1.0553P] where P = (F_o² + 2F_c²)/3
3331 reflections	(Δ/σ)_max = 0.002
119 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₀H₇BrO₂	V = 1755.62 (5) Å³
M_r = 239.07	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 10.8301 (2) Å	µ = 4.64 mm⁻¹
b = 7.4630 (1) Å	T = 100 K
c = 21.7213 (3) Å	0.26 × 0.19 × 0.18 mm

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	3331 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2689 reflections with I > 2σ(I)
T_min = 0.377, T_max = 0.482	R_int = 0.038
43601 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	0 restraints
wR(F²) = 0.058	H-atom parameters constrained
S = 1.04	Δρ_max = 0.47 e Å⁻³
3331 reflections	Δρ_min = −0.28 e Å⁻³
119 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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

	x	y	z	U_iso*/U_eq
Br1	0.176439 (12)	0.162250 (19)	0.544115 (6)	0.01904 (5)
O1	0.36814 (9)	−0.10002 (14)	0.30247 (4)	0.01671 (18)
O2	0.36732 (9)	−0.25959 (15)	0.18927 (5)	0.0228 (2)
C1	0.33614 (11)	−0.03183 (18)	0.35866 (6)	0.0153 (2)
C2	0.41792 (12)	0.03133 (19)	0.40293 (6)	0.0177 (3)
H2A	0.5045	0.0339	0.3961	0.021*
C3	0.36627 (13)	0.09040 (19)	0.45760 (6)	0.0176 (2)
H3A	0.4182	0.1340	0.4895	0.021*
C4	0.23784 (12)	0.08646 (19)	0.46632 (6)	0.0163 (2)
C5	0.15642 (12)	0.02766 (19)	0.42185 (6)	0.0169 (2)
H5A	0.0697	0.0287	0.4285	0.020*
C6	0.20783 (12)	−0.03389 (18)	0.36629 (6)	0.0151 (2)
C7	0.15886 (12)	−0.10978 (19)	0.31084 (6)	0.0165 (2)
H7A	0.0743	−0.1294	0.3013	0.020*
C8	0.25797 (12)	−0.14821 (19)	0.27452 (6)	0.0161 (2)
C9	0.26702 (12)	−0.23368 (19)	0.21372 (6)	0.0171 (2)
C10	0.14699 (13)	−0.2835 (2)	0.18369 (7)	0.0214 (3)
H10D	0.1630	−0.3645	0.1491	0.032*
H10A	0.1059	−0.1750	0.1686	0.032*
H10B	0.0937	−0.3436	0.2138	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02043 (7)	0.02101 (8)	0.01568 (7)	0.00053 (5)	0.00383 (5)	0.00000 (5)
O1	0.0123 (4)	0.0231 (5)	0.0147 (4)	−0.0003 (4)	0.0008 (3)	−0.0005 (4)
O2	0.0171 (4)	0.0314 (6)	0.0200 (5)	0.0005 (4)	0.0031 (4)	−0.0025 (4)
C1	0.0133 (5)	0.0173 (6)	0.0152 (5)	0.0004 (4)	0.0014 (4)	0.0025 (5)
C2	0.0133 (5)	0.0216 (7)	0.0180 (6)	0.0002 (5)	−0.0002 (5)	0.0007 (5)
C3	0.0157 (5)	0.0190 (6)	0.0183 (6)	0.0003 (5)	−0.0021 (5)	0.0011 (5)
C4	0.0179 (6)	0.0168 (6)	0.0141 (5)	0.0006 (5)	0.0029 (4)	0.0020 (5)
C5	0.0144 (6)	0.0182 (6)	0.0182 (6)	−0.0003 (5)	0.0019 (4)	0.0018 (5)
C6	0.0136 (5)	0.0168 (6)	0.0149 (5)	−0.0002 (5)	0.0008 (4)	0.0028 (5)
C7	0.0134 (5)	0.0192 (6)	0.0170 (6)	−0.0004 (5)	−0.0008 (4)	0.0022 (5)
C8	0.0132 (5)	0.0183 (6)	0.0167 (5)	−0.0005 (5)	−0.0008 (4)	0.0031 (5)
C9	0.0169 (6)	0.0178 (6)	0.0167 (6)	0.0002 (5)	−0.0003 (5)	0.0028 (5)
C10	0.0176 (6)	0.0277 (7)	0.0187 (6)	0.0001 (6)	−0.0028 (5)	−0.0001 (6)

Geometric parameters (Å, º) top

Br1—C4	1.9020 (13)	C5—C6	1.4062 (18)
O1—C1	1.3669 (16)	C5—H5A	0.9500
O1—C8	1.3862 (16)	C6—C7	1.4327 (19)
O2—C9	1.2245 (17)	C7—C8	1.3626 (18)
C1—C2	1.3898 (18)	C7—H7A	0.9500
C1—C6	1.3995 (18)	C8—C9	1.4699 (19)
C2—C3	1.3847 (19)	C9—C10	1.5013 (19)
C2—H2A	0.9500	C10—H10D	0.9800
C3—C4	1.4041 (19)	C10—H10A	0.9800
C3—H3A	0.9500	C10—H10B	0.9800
C4—C5	1.3795 (19)

C1—O1—C8	105.63 (10)	C1—C6—C7	105.80 (11)
O1—C1—C2	125.63 (11)	C5—C6—C7	134.76 (12)
O1—C1—C6	110.70 (11)	C8—C7—C6	106.16 (11)
C2—C1—C6	123.67 (12)	C8—C7—H7A	126.9
C3—C2—C1	116.36 (12)	C6—C7—H7A	126.9
C3—C2—H2A	121.8	C7—C8—O1	111.71 (12)
C1—C2—H2A	121.8	C7—C8—C9	131.61 (12)
C2—C3—C4	120.61 (13)	O1—C8—C9	116.66 (11)
C2—C3—H3A	119.7	O2—C9—C8	121.15 (12)
C4—C3—H3A	119.7	O2—C9—C10	122.72 (13)
C5—C4—C3	123.05 (12)	C8—C9—C10	116.12 (12)
C5—C4—Br1	119.55 (10)	C9—C10—H10D	109.5
C3—C4—Br1	117.38 (10)	C9—C10—H10A	109.5
C4—C5—C6	116.86 (12)	H10D—C10—H10A	109.5
C4—C5—H5A	121.6	C9—C10—H10B	109.5
C6—C5—H5A	121.6	H10D—C10—H10B	109.5
C1—C6—C5	119.42 (12)	H10A—C10—H10B	109.5

C8—O1—C1—C2	179.08 (13)	C4—C5—C6—C1	−0.3 (2)
C8—O1—C1—C6	−0.81 (15)	C4—C5—C6—C7	177.41 (15)
O1—C1—C2—C3	−178.27 (13)	C1—C6—C7—C8	0.26 (15)
C6—C1—C2—C3	1.6 (2)	C5—C6—C7—C8	−177.71 (15)
C1—C2—C3—C4	−0.5 (2)	C6—C7—C8—O1	−0.78 (16)
C2—C3—C4—C5	−1.0 (2)	C6—C7—C8—C9	177.28 (14)
C2—C3—C4—Br1	177.76 (11)	C1—O1—C8—C7	1.00 (15)
C3—C4—C5—C6	1.4 (2)	C1—O1—C8—C9	−177.38 (12)
Br1—C4—C5—C6	−177.32 (10)	C7—C8—C9—O2	−178.33 (15)
O1—C1—C6—C5	178.69 (12)	O1—C8—C9—O2	−0.3 (2)
C2—C1—C6—C5	−1.2 (2)	C7—C8—C9—C10	2.6 (2)
O1—C1—C6—C7	0.35 (15)	O1—C8—C9—C10	−179.41 (12)
C2—C1—C6—C7	−179.53 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O2ⁱ	0.95	2.45	3.3495 (16)	158

Symmetry code: (i) x−1/2, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₇BrO₂
M_r	239.07
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	10.8301 (2), 7.4630 (1), 21.7213 (3)
V (Å³)	1755.62 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	4.64
Crystal size (mm)	0.26 × 0.19 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.377, 0.482
No. of measured, independent and observed [I > 2σ(I)] reflections	43601, 3331, 2689
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.769

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.058, 1.04
No. of reflections	3331
No. of parameters	119
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.28

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O2ⁱ	0.95	2.45	3.3495 (16)	158

Symmetry code: (i) x−1/2, y, −z+1/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160) and the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University.

References

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