Ethyl 5-bromo-1-benzofuran-2-carboxyl-ate.

In the title compound, C(11)H(9)BrO(3), the benzofuran fused-ring system is almost planar, with a maximum atomic deviation of 0.024 (5) Å; the carboxyl -CO(2) fragment is aligned at 4.8 (7)° with respect to the fused-ring plane. Weak inter-molecular C-H⋯O hydrogen bonding is present in the crystal structure. π-π stacking is also observed between parallel mol-ecules, the centroid-centroid distance between benzene and furan rings of adjacent mol-ecules being 3.662 (3) Å.

Related literature

For our previous reports of the pharmacological properties of benzofurans, see: Abdel-Aziz & Mekawey (2009 ▶); Abdel-Aziz et al. (2009 ▶). For a related structure, see: Kossakowski et al. (2005 ▶).

Experimental

Crystal data

C11H9BrO3

M = 269.09

Monoclinic,

a = 3.8869 (3) Å

b = 23.780 (2) Å

c = 11.0820 (7) Å

β = 96.905 (8)°

V = 1016.89 (13) Å3

Z = 4

Mo Kα radiation

μ = 4.02 mm−1

T = 100 K

0.30 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.378, T max = 0.689

6060 measured reflections

2250 independent reflections

1843 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.109

S = 1.18

2250 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.97 e Å−3

Δρmin = −0.71 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811005897/xu5164sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811005897/xu5164Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H9BrO3	F(000) = 536
Mr = 269.09	Dx = 1.758 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2599 reflections
a = 3.8869 (3) Å	θ = 2.5–29.3°
b = 23.780 (2) Å	µ = 4.02 mm−1
c = 11.0820 (7) Å	T = 100 K
β = 96.905 (8)°	Prism, colorless
V = 1016.89 (13) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	2250 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1843 reflections with I > 2σ(I)
Mirror	Rint = 0.045
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.5°
ω scans	h = −3→5
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −30→30
Tmin = 0.378, Tmax = 0.689	l = −13→14
6060 measured reflections

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.18	w = 1/[σ2(Fo2) + (0.0086P)2 + 5.1797P] where P = (Fo2 + 2Fc2)/3
2250 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.97 e Å−3
0 restraints	Δρmin = −0.71 e Å−3

	x	y	z	Uiso*/Ueq
Br1	0.84947 (14)	0.52531 (2)	0.18162 (5)	0.02119 (16)
O1	0.2581 (9)	0.32380 (14)	0.4040 (3)	0.0157 (7)
O2	0.0007 (10)	0.25870 (14)	0.5783 (3)	0.0228 (9)
O3	0.1752 (9)	0.32488 (14)	0.7194 (3)	0.0165 (8)
C1	0.3994 (13)	0.3662 (2)	0.3427 (4)	0.0146 (10)
C2	0.4194 (14)	0.3670 (2)	0.2183 (4)	0.0189 (11)
H2	0.3416	0.3363	0.1672	0.023*
C3	0.5588 (15)	0.4150 (2)	0.1733 (4)	0.0216 (12)
H3	0.5746	0.4181	0.0886	0.026*
C4	0.6767 (13)	0.4590 (2)	0.2510 (4)	0.0163 (11)
C5	0.6666 (13)	0.4576 (2)	0.3740 (4)	0.0151 (10)
H5	0.7541	0.4878	0.4248	0.018*
C6	0.5205 (12)	0.4095 (2)	0.4220 (4)	0.0135 (10)
C7	0.4517 (13)	0.3916 (2)	0.5397 (4)	0.0153 (10)
H7	0.5060	0.4113	0.6141	0.018*
C8	0.2932 (14)	0.3408 (2)	0.5243 (4)	0.0161 (11)
C9	0.1403 (13)	0.3029 (2)	0.6073 (4)	0.0157 (10)
C10	0.0273 (14)	0.2924 (2)	0.8131 (4)	0.0202 (11)
H10A	0.1957	0.2639	0.8488	0.024*
H10B	−0.1857	0.2728	0.7775	0.024*
C11	−0.0555 (14)	0.3333 (2)	0.9091 (4)	0.0202 (11)
H11A	−0.1540	0.3130	0.9738	0.030*
H11B	−0.2234	0.3611	0.8728	0.030*
H11C	0.1571	0.3526	0.9433	0.030*

	U11	U22	U33	U12	U13	U23
Br1	0.0225 (3)	0.0210 (3)	0.0205 (3)	−0.0006 (2)	0.0046 (2)	0.0051 (2)
O1	0.020 (2)	0.0151 (17)	0.0107 (15)	−0.0015 (15)	−0.0019 (14)	−0.0010 (14)
O2	0.032 (2)	0.0169 (19)	0.0191 (18)	−0.0038 (17)	0.0022 (17)	−0.0014 (15)
O3	0.019 (2)	0.0196 (18)	0.0108 (15)	−0.0032 (15)	0.0007 (14)	0.0015 (14)
C1	0.015 (3)	0.016 (2)	0.013 (2)	0.003 (2)	−0.0009 (19)	0.0018 (19)
C2	0.021 (3)	0.022 (3)	0.013 (2)	0.002 (2)	−0.001 (2)	−0.002 (2)
C3	0.032 (3)	0.021 (3)	0.013 (2)	0.004 (2)	0.006 (2)	0.002 (2)
C4	0.013 (3)	0.018 (2)	0.019 (2)	0.002 (2)	0.005 (2)	0.007 (2)
C5	0.013 (3)	0.014 (2)	0.018 (2)	0.000 (2)	0.001 (2)	−0.003 (2)
C6	0.008 (2)	0.018 (2)	0.012 (2)	0.001 (2)	−0.0063 (19)	−0.0007 (19)
C7	0.016 (3)	0.016 (2)	0.013 (2)	0.004 (2)	−0.001 (2)	−0.0006 (19)
C8	0.021 (3)	0.016 (2)	0.010 (2)	0.007 (2)	0.000 (2)	0.0000 (19)
C9	0.014 (3)	0.019 (3)	0.013 (2)	0.005 (2)	−0.003 (2)	0.001 (2)
C10	0.023 (3)	0.022 (3)	0.016 (2)	−0.003 (2)	0.004 (2)	0.006 (2)
C11	0.020 (3)	0.027 (3)	0.014 (2)	−0.007 (2)	0.001 (2)	0.003 (2)

Br1—C4	1.912 (5)	C5—C6	1.410 (7)
O1—C1	1.367 (6)	C5—H5	0.9500
O1—C8	1.384 (5)	C6—C7	1.428 (6)
O2—C9	1.208 (6)	C7—C8	1.357 (7)
O3—C9	1.340 (5)	C7—H7	0.9500
O3—C10	1.465 (6)	C8—C9	1.464 (7)
C1—C2	1.390 (6)	C10—C11	1.505 (7)
C1—C6	1.398 (7)	C10—H10A	0.9900
C2—C3	1.382 (7)	C10—H10B	0.9900
C2—H2	0.9500	C11—H11A	0.9800
C3—C4	1.397 (7)	C11—H11B	0.9800
C3—H3	0.9500	C11—H11C	0.9800
C4—C5	1.369 (6)
C1—O1—C8	105.3 (4)	C8—C7—H7	126.8
C9—O3—C10	116.5 (4)	C6—C7—H7	126.8
O1—C1—C2	125.2 (4)	C7—C8—O1	111.9 (4)
O1—C1—C6	110.8 (4)	C7—C8—C9	133.0 (4)
C2—C1—C6	124.0 (5)	O1—C8—C9	115.1 (4)
C3—C2—C1	116.1 (5)	O2—C9—O3	125.3 (5)
C3—C2—H2	121.9	O2—C9—C8	124.9 (4)
C1—C2—H2	121.9	O3—C9—C8	109.8 (4)
C2—C3—C4	120.6 (4)	O3—C10—C11	107.2 (4)
C2—C3—H3	119.7	O3—C10—H10A	110.3
C4—C3—H3	119.7	C11—C10—H10A	110.3
C5—C4—C3	123.4 (5)	O3—C10—H10B	110.3
C5—C4—Br1	118.2 (4)	C11—C10—H10B	110.3
C3—C4—Br1	118.4 (4)	H10A—C10—H10B	108.5
C4—C5—C6	117.1 (4)	C10—C11—H11A	109.5
C4—C5—H5	121.5	C10—C11—H11B	109.5
C6—C5—H5	121.5	H11A—C11—H11B	109.5
C1—C6—C5	118.8 (4)	C10—C11—H11C	109.5
C1—C6—C7	105.6 (4)	H11A—C11—H11C	109.5
C5—C6—C7	135.6 (5)	H11B—C11—H11C	109.5
C8—C7—C6	106.4 (4)
C8—O1—C1—C2	−179.8 (5)	C4—C5—C6—C7	−178.1 (5)
C8—O1—C1—C6	−0.3 (5)	C1—C6—C7—C8	−1.0 (6)
O1—C1—C2—C3	177.3 (5)	C5—C6—C7—C8	177.8 (6)
C6—C1—C2—C3	−2.1 (8)	C6—C7—C8—O1	0.9 (6)
C1—C2—C3—C4	1.2 (8)	C6—C7—C8—C9	−175.5 (5)
C2—C3—C4—C5	0.7 (8)	C1—O1—C8—C7	−0.4 (6)
C2—C3—C4—Br1	−177.6 (4)	C1—O1—C8—C9	176.7 (4)
C3—C4—C5—C6	−1.6 (7)	C10—O3—C9—O2	−0.7 (7)
Br1—C4—C5—C6	176.6 (4)	C10—O3—C9—C8	178.6 (4)
O1—C1—C6—C5	−178.3 (4)	C7—C8—C9—O2	178.6 (6)
C2—C1—C6—C5	1.2 (8)	O1—C8—C9—O2	2.3 (7)
O1—C1—C6—C7	0.8 (5)	C7—C8—C9—O3	−0.7 (8)
C2—C1—C6—C7	−179.7 (5)	O1—C8—C9—O3	−177.1 (4)
C4—C5—C6—C1	0.7 (7)	C9—O3—C10—C11	−154.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2i	0.95	2.57	3.400 (6)	146
C11—H11A···O2ii	0.98	2.53	3.472 (6)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2i	0.95	2.57	3.400 (6)	146
C11—H11A⋯O2ii	0.98	2.53	3.472 (6)	160

Symmetry codes: (i) ; (ii) .