3-(2-Bromo-eth-oxy)-4-(4-bromo-phen-yl)furan-5(2H)-one.

In the title compound, C(12)H(10)Br(2)O(3), the dihedral angle between the furan-5(2H)-one ring and the benzene ring is 1.2 (3)°. Two intra-molecular C-H⋯O inter-actions occur in the mol-ecule, both of which generate S(6) rings. The bromo-ethyl fragment is disordered over two sets of sites in a 0.773 (8):0.227 (8) ratio. In the crystal, inversion dimers linked by pairs of C-H⋯π inter-actions occur.

Related literature

For background to furan­ones, see: Bailly et al. (2008 ▶); Weber et al. (2005 ▶).

Experimental

Crystal data

C12H10Br2O3

M = 362.02

Monoclinic,

a = 8.6171 (13) Å

b = 10.4434 (16) Å

c = 13.958 (2) Å

β = 95.831 (3)°

V = 1249.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 6.48 mm−1

T = 298 K

0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.357, T max = 0.564

7195 measured reflections

2582 independent reflections

1765 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.187

S = 1.05

2582 reflections

155 parameters

29 restraints

H-atom parameters constrained

Δρmax = 1.37 e Å−3

Δρmin = −1.15 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810044508/hb5720sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044508/hb5720Isup2.hkl

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

C12H10Br2O3	F(000) = 704
Mr = 362.02	Dx = 1.924 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1832 reflections
a = 8.6171 (13) Å	θ = 2.6–26.1°
b = 10.4434 (16) Å	µ = 6.48 mm−1
c = 13.958 (2) Å	T = 298 K
β = 95.831 (3)°	Block, colorless
V = 1249.6 (3) Å3	0.20 × 0.10 × 0.10 mm
Z = 4

Bruker SMART APEX CCD diffractometer	2582 independent reflections
Radiation source: fine-focus sealed tube	1765 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 26.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.357, Tmax = 0.564	k = −6→13
7195 measured reflections	l = −17→17

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.187	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.1008P)2 + 2.0749P] where P = (Fo2 + 2Fc2)/3
2582 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 1.37 e Å−3
29 restraints	Δρmin = −1.15 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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	Occ. (<1)
Br1	0.50480 (10)	0.34315 (8)	0.21873 (6)	0.0737 (4)
Br2A	0.2920 (5)	0.92938 (17)	0.48473 (18)	0.0900 (8)	0.773 (8)
Br2B	0.2207 (13)	0.9329 (7)	0.4681 (7)	0.0900 (8)	0.227 (8)
C1	0.2553 (7)	0.4284 (6)	0.4943 (5)	0.0478 (14)
C2	0.2843 (9)	0.3041 (7)	0.4667 (5)	0.0600 (18)
H2	0.2534	0.2368	0.5041	0.072*
C3	0.3561 (9)	0.2770 (7)	0.3870 (6)	0.0627 (18)
H3	0.3711	0.1923	0.3696	0.075*
C4	0.4069 (8)	0.3750 (7)	0.3319 (5)	0.0516 (15)
C5	0.3815 (9)	0.5002 (6)	0.3576 (5)	0.0562 (17)
H5	0.4147	0.5668	0.3205	0.067*
C6	0.3076 (8)	0.5270 (6)	0.4379 (5)	0.0566 (17)
H6	0.2920	0.6117	0.4549	0.068*
C7	0.1745 (8)	0.4574 (7)	0.5800 (5)	0.0491 (15)
C8	0.1126 (9)	0.3606 (9)	0.6426 (6)	0.067 (2)
C9	0.0595 (10)	0.5553 (9)	0.7061 (5)	0.069 (2)
H9A	0.1208	0.5923	0.7614	0.083*
H9B	−0.0425	0.5954	0.6988	0.083*
C10	0.1405 (8)	0.5708 (7)	0.6165 (5)	0.0548 (16)
C11	0.1273 (12)	0.7904 (7)	0.6271 (7)	0.092 (3)
H11A	0.1406	0.7743	0.6959	0.110*	0.773 (8)
H11B	0.0172	0.8050	0.6085	0.110*	0.773 (8)
H11C	0.2125	0.8202	0.6724	0.110*	0.227 (8)
H11D	0.0412	0.7671	0.6633	0.110*	0.227 (8)
C12A	0.2190 (15)	0.9106 (9)	0.6052 (6)	0.0900 (8)	0.773 (8)
H12A	0.3085	0.9160	0.6532	0.108*	0.773 (8)
H12B	0.1534	0.9840	0.6150	0.108*	0.773 (8)
C12B	0.076 (3)	0.899 (2)	0.5565 (19)	0.0900 (8)	0.227 (8)
H12C	0.0599	0.9763	0.5929	0.108*	0.227 (8)
H12D	−0.0235	0.8763	0.5214	0.108*	0.227 (8)
O1	0.1076 (8)	0.2448 (6)	0.6373 (5)	0.0886 (18)
O2	0.0467 (7)	0.4217 (6)	0.7160 (4)	0.0808 (17)
O3	0.1739 (7)	0.6861 (5)	0.5802 (4)	0.0731 (16)

	U11	U22	U33	U12	U13	U23
Br1	0.0856 (6)	0.0761 (6)	0.0639 (5)	0.0142 (4)	0.0292 (4)	−0.0115 (4)
Br2A	0.102 (2)	0.0635 (7)	0.1132 (11)	−0.0048 (10)	0.0551 (13)	−0.0016 (6)
Br2B	0.102 (2)	0.0635 (7)	0.1132 (11)	−0.0048 (10)	0.0551 (13)	−0.0016 (6)
C1	0.046 (3)	0.045 (4)	0.052 (3)	−0.003 (3)	0.008 (3)	0.007 (3)
C2	0.080 (5)	0.038 (4)	0.064 (4)	−0.003 (3)	0.016 (4)	0.012 (3)
C3	0.076 (5)	0.038 (4)	0.076 (5)	0.008 (3)	0.017 (4)	−0.002 (3)
C4	0.055 (4)	0.049 (4)	0.053 (3)	0.004 (3)	0.015 (3)	−0.008 (3)
C5	0.079 (5)	0.040 (4)	0.054 (4)	−0.005 (3)	0.024 (3)	0.002 (3)
C6	0.076 (5)	0.038 (3)	0.060 (4)	−0.004 (3)	0.028 (3)	0.006 (3)
C7	0.052 (4)	0.054 (4)	0.043 (3)	−0.005 (3)	0.012 (3)	0.005 (3)
C8	0.060 (4)	0.081 (6)	0.061 (4)	−0.002 (4)	0.015 (3)	0.022 (4)
C9	0.074 (5)	0.089 (6)	0.049 (4)	−0.004 (4)	0.026 (3)	0.000 (4)
C10	0.053 (4)	0.068 (5)	0.046 (3)	0.000 (3)	0.018 (3)	0.001 (3)
C11	0.116 (7)	0.071 (5)	0.096 (6)	−0.002 (5)	0.054 (5)	−0.024 (4)
C12A	0.102 (2)	0.0635 (7)	0.1132 (11)	−0.0048 (10)	0.0551 (13)	−0.0016 (6)
C12B	0.102 (2)	0.0635 (7)	0.1132 (11)	−0.0048 (10)	0.0551 (13)	−0.0016 (6)
O1	0.106 (5)	0.067 (4)	0.099 (4)	−0.010 (3)	0.037 (3)	0.031 (3)
O2	0.084 (4)	0.098 (5)	0.067 (3)	−0.003 (3)	0.039 (3)	0.021 (3)
O3	0.111 (4)	0.048 (3)	0.069 (3)	0.000 (3)	0.053 (3)	−0.006 (2)

Br1—C4	1.895 (6)	C8—O2	1.377 (10)
Br2A—C12A	1.864 (5)	C9—O2	1.407 (11)
Br2B—C12B	1.878 (6)	C9—C10	1.501 (9)
C1—C2	1.384 (10)	C9—H9A	0.9700
C1—C6	1.397 (9)	C9—H9B	0.9700
C1—C7	1.476 (9)	C10—O3	1.348 (8)
C2—C3	1.357 (11)	C11—O3	1.352 (9)
C2—H2	0.9300	C11—C12A	1.531 (5)
C3—C4	1.378 (10)	C11—C12B	1.539 (6)
C3—H3	0.9300	C11—H11A	0.9700
C4—C5	1.379 (10)	C11—H11B	0.9700
C5—C6	1.372 (9)	C11—H11C	0.9700
C5—H5	0.9300	C11—H11D	0.9700
C6—H6	0.9300	C12A—H12A	0.9700
C7—C10	1.334 (10)	C12A—H12B	0.9700
C7—C8	1.471 (10)	C12B—H12C	0.9700
C8—O1	1.212 (10)	C12B—H12D	0.9700
C2—C1—C6	117.2 (6)	O3—C11—C12B	111.5 (12)
C2—C1—C7	122.0 (6)	C12A—C11—C12B	52.3 (13)
C6—C1—C7	120.8 (6)	O3—C11—H11A	109.1
C3—C2—C1	122.2 (6)	C12A—C11—H11A	109.1
C3—C2—H2	118.9	C12B—C11—H11A	139.4
C1—C2—H2	118.9	O3—C11—H11B	109.1
C2—C3—C4	120.0 (6)	C12A—C11—H11B	109.1
C2—C3—H3	120.0	C12B—C11—H11B	60.0
C4—C3—H3	120.0	H11A—C11—H11B	107.9
C3—C4—C5	119.4 (6)	O3—C11—H11C	109.3
C3—C4—Br1	121.9 (5)	C12A—C11—H11C	59.7
C5—C4—Br1	118.6 (5)	C12B—C11—H11C	109.3
C6—C5—C4	120.3 (6)	H11A—C11—H11C	53.5
C6—C5—H5	119.9	H11B—C11—H11C	141.2
C4—C5—H5	119.9	O3—C11—H11D	109.3
C5—C6—C1	120.8 (7)	C12A—C11—H11D	138.3
C5—C6—H6	119.6	C12B—C11—H11D	109.3
C1—C6—H6	119.6	H11A—C11—H11D	57.4
C10—C7—C8	106.0 (6)	H11B—C11—H11D	53.1
C10—C7—C1	129.2 (6)	H11C—C11—H11D	108.0
C8—C7—C1	124.8 (7)	C11—C12A—Br2A	119.6 (6)
O1—C8—O2	119.5 (7)	C11—C12A—H12A	107.4
O1—C8—C7	131.4 (8)	Br2A—C12A—H12A	107.4
O2—C8—C7	109.0 (7)	C11—C12A—H12B	107.4
O2—C9—C10	103.7 (6)	Br2A—C12A—H12B	107.4
O2—C9—H9A	111.0	H12A—C12A—H12B	106.9
C10—C9—H9A	111.0	C11—C12B—Br2B	113.0 (7)
O2—C9—H9B	111.0	C11—C12B—H12C	109.0
C10—C9—H9B	111.0	Br2B—C12B—H12C	109.0
H9A—C9—H9B	109.0	C11—C12B—H12D	109.0
C7—C10—O3	125.9 (6)	Br2B—C12B—H12D	109.0
C7—C10—C9	111.1 (6)	H12C—C12B—H12D	107.8
O3—C10—C9	123.0 (6)	C8—O2—C9	110.1 (6)
O3—C11—C12A	112.3 (6)	C10—O3—C11	116.9 (5)
C6—C1—C2—C3	−1.9 (11)	C8—C7—C10—O3	−178.9 (7)
C7—C1—C2—C3	178.8 (7)	C1—C7—C10—O3	0.4 (12)
C1—C2—C3—C4	1.8 (12)	C8—C7—C10—C9	1.8 (8)
C2—C3—C4—C5	−1.1 (11)	C1—C7—C10—C9	−178.9 (7)
C2—C3—C4—Br1	−178.9 (6)	O2—C9—C10—C7	−1.5 (9)
C3—C4—C5—C6	0.5 (11)	O2—C9—C10—O3	179.1 (7)
Br1—C4—C5—C6	178.4 (6)	O3—C11—C12A—Br2A	31.9 (14)
C4—C5—C6—C1	−0.6 (12)	C12B—C11—C12A—Br2A	−68.7 (13)
C2—C1—C6—C5	1.3 (11)	O3—C11—C12B—Br2B	−49 (2)
C7—C1—C6—C5	−179.4 (7)	C12A—C11—C12B—Br2B	53.0 (14)
C2—C1—C7—C10	178.8 (7)	O1—C8—O2—C9	−177.4 (8)
C6—C1—C7—C10	−0.5 (11)	C7—C8—O2—C9	0.4 (8)
C2—C1—C7—C8	−2.0 (11)	C10—C9—O2—C8	0.6 (8)
C6—C1—C7—C8	178.7 (7)	C7—C10—O3—C11	179.0 (8)
C10—C7—C8—O1	176.1 (9)	C9—C10—O3—C11	−1.7 (11)
C1—C7—C8—O1	−3.2 (13)	C12A—C11—O3—C10	158.9 (8)
C10—C7—C8—O2	−1.4 (8)	C12B—C11—O3—C10	−144.3 (13)
C1—C7—C8—O2	179.3 (6)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.93	2.35	3.018 (10)	129
C6—H6···O3	0.93	2.25	2.916 (8)	128
C9—H9B···Cg1i	0.97	2.80	3.632 (9)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1	0.93	2.35	3.018 (10)	129
C6—H6⋯O3	0.93	2.25	2.916 (8)	128
C9—H9B⋯Cg1i	0.97	2.80	3.632 (9)	144

Symmetry code: (i) .