2,4-Dibromo-2,3-dihydro-1H-inden-1-yl acetate.

In the title compound, C(11)H(10)Br(2)O(2), the cyclo-pentene ring fused to the benzene ring adopts an envelope conformation, with the C atom attached to the Br atom as the flap. The crystal structure does not exhibit any classical hydrogen bonds. The mol-ecular packing is stabilized by van der Waals forces and π-π stacking inter-actions with a centroid-centroid distance of 3.811 (4) Å.

Related literature

For bromination of hydro­carbons, see: Catto et al. (2010 ▶); Erenler & Çakmak (2004 ▶); Erenler et al. (2006 ▶); McClure et al. (2011 ▶); Mitrochkine et al. (1995 ▶); Snyder & Brill (2011 ▶); Wu (2006 ▶); Çakmak et al. (2006 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C11H10Br2O2

M = 333.99

Triclinic,

a = 8.1423 (7) Å

b = 8.6891 (9) Å

c = 9.0028 (8) Å

α = 76.163 (8)°

β = 68.105 (7)°

γ = 86.397 (8)°

V = 573.60 (10) Å3

Z = 2

Mo Kα radiation

μ = 7.04 mm−1

T = 296 K

0.43 × 0.35 × 0.28 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.152, T max = 0.243

6542 measured reflections

2635 independent reflections

1958 reflections with I > 2σ(I)

R int = 0.110

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.178

S = 1.02

2635 reflections

137 parameters

H-atom parameters constrained

Δρmax = 1.20 e Å−3

Δρmin = −1.42 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812023173/fj2559sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023173/fj2559Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812023173/fj2559Isup3.cml

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

C11H10Br2O2	Z = 2
Mr = 333.99	F(000) = 324
Triclinic, P1	Dx = 1.934 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1423 (7) Å	Cell parameters from 9714 reflections
b = 8.6891 (9) Å	θ = 2.4–28.1°
c = 9.0028 (8) Å	µ = 7.04 mm−1
α = 76.163 (8)°	T = 296 K
β = 68.105 (7)°	Prism, colourless
γ = 86.397 (8)°	0.43 × 0.35 × 0.28 mm
V = 573.60 (10) Å3

Stoe IPDS 2 diffractometer	2635 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1958 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.110
Detector resolution: 6.67 pixels mm-1	θmax = 27.5°, θmin = 2.5°
ω scans	h = −10→10
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −11→10
Tmin = 0.152, Tmax = 0.243	l = −11→11
6542 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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.1053P)2] where P = (Fo2 + 2Fc2)/3
2635 reflections	(Δ/σ)max < 0.001
137 parameters	Δρmax = 1.20 e Å−3
0 restraints	Δρmin = −1.42 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
Br1	0.22277 (8)	0.18390 (9)	1.10206 (9)	0.0641 (3)
Br2	0.91526 (9)	0.24936 (9)	0.49626 (8)	0.0579 (3)
O1	0.9902 (5)	0.1989 (5)	0.8133 (5)	0.0464 (11)
O2	1.2454 (6)	0.3332 (6)	0.6377 (6)	0.0625 (16)
C1	0.7425 (7)	0.3340 (6)	0.9593 (7)	0.0433 (17)
C2	0.7505 (8)	0.3703 (7)	1.0998 (8)	0.0495 (17)
C3	0.6006 (10)	0.3485 (8)	1.2402 (8)	0.0549 (19)
C4	0.4421 (9)	0.2927 (8)	1.2408 (8)	0.0527 (19)
C5	0.4366 (8)	0.2609 (7)	1.1011 (8)	0.0497 (17)
C6	0.5867 (7)	0.2826 (7)	0.9560 (7)	0.0438 (17)
C7	0.6106 (7)	0.2538 (7)	0.7923 (7)	0.0472 (17)
C8	0.7877 (7)	0.3406 (7)	0.6838 (7)	0.0446 (17)
C9	0.8911 (7)	0.3415 (6)	0.7950 (7)	0.0425 (14)
C10	1.1652 (8)	0.2097 (8)	0.7179 (8)	0.0488 (17)
C11	1.2441 (10)	0.0501 (9)	0.7271 (11)	0.065 (3)
H2	0.85540	0.40870	1.09820	0.0590*
H3	0.60410	0.37060	1.33510	0.0660*
H4	0.34100	0.27740	1.33620	0.0630*
H7A	0.51600	0.29880	0.75610	0.0570*
H7B	0.61690	0.14150	0.79440	0.0570*
H8	0.76310	0.45080	0.64130	0.0530*
H9	0.96600	0.43760	0.75890	0.0510*
H11A	1.18960	−0.01350	0.68340	0.0970*
H11B	1.22470	−0.00010	0.83970	0.0970*
H11C	1.36900	0.06100	0.66390	0.0970*

	U11	U22	U33	U12	U13	U23
Br1	0.0461 (4)	0.0769 (5)	0.0653 (5)	−0.0077 (3)	−0.0103 (3)	−0.0237 (4)
Br2	0.0559 (4)	0.0717 (5)	0.0471 (4)	0.0049 (3)	−0.0153 (3)	−0.0228 (3)
O1	0.045 (2)	0.0381 (19)	0.056 (2)	0.0031 (15)	−0.0190 (17)	−0.0109 (17)
O2	0.051 (2)	0.061 (3)	0.067 (3)	−0.006 (2)	−0.014 (2)	−0.010 (2)
C1	0.048 (3)	0.036 (3)	0.046 (3)	0.001 (2)	−0.016 (2)	−0.012 (2)
C2	0.054 (3)	0.042 (3)	0.059 (3)	0.001 (2)	−0.026 (3)	−0.015 (3)
C3	0.070 (4)	0.051 (3)	0.053 (3)	0.013 (3)	−0.029 (3)	−0.022 (3)
C4	0.061 (4)	0.051 (3)	0.043 (3)	0.012 (3)	−0.015 (3)	−0.015 (3)
C5	0.051 (3)	0.043 (3)	0.052 (3)	0.008 (2)	−0.016 (2)	−0.012 (2)
C6	0.046 (3)	0.043 (3)	0.043 (3)	0.006 (2)	−0.018 (2)	−0.010 (2)
C7	0.040 (3)	0.052 (3)	0.049 (3)	−0.002 (2)	−0.014 (2)	−0.014 (3)
C8	0.046 (3)	0.045 (3)	0.045 (3)	0.005 (2)	−0.019 (2)	−0.012 (2)
C9	0.040 (2)	0.033 (2)	0.053 (3)	0.0027 (19)	−0.017 (2)	−0.008 (2)
C10	0.042 (3)	0.056 (3)	0.055 (3)	0.007 (2)	−0.022 (2)	−0.020 (3)
C11	0.062 (4)	0.058 (4)	0.086 (5)	0.012 (3)	−0.031 (4)	−0.034 (4)

Br1—C5	1.900 (7)	C7—C8	1.528 (9)
Br2—C8	1.946 (6)	C8—C9	1.531 (8)
O1—C9	1.446 (7)	C10—C11	1.489 (11)
O1—C10	1.357 (8)	C2—H2	0.9300
O2—C10	1.210 (9)	C3—H3	0.9300
C1—C2	1.400 (9)	C4—H4	0.9300
C1—C6	1.384 (9)	C7—H7A	0.9700
C1—C9	1.512 (8)	C7—H7B	0.9700
C2—C3	1.374 (10)	C8—H8	0.9800
C3—C4	1.405 (11)	C9—H9	0.9800
C4—C5	1.368 (9)	C11—H11A	0.9600
C5—C6	1.399 (9)	C11—H11B	0.9600
C6—C7	1.493 (8)	C11—H11C	0.9600
C9—O1—C10	116.4 (5)	C1—C2—H2	121.00
C2—C1—C6	121.9 (6)	C3—C2—H2	121.00
C2—C1—C9	128.1 (6)	C2—C3—H3	120.00
C6—C1—C9	110.0 (5)	C4—C3—H3	120.00
C1—C2—C3	118.9 (6)	C3—C4—H4	120.00
C2—C3—C4	120.1 (6)	C5—C4—H4	120.00
C3—C4—C5	120.0 (6)	C6—C7—H7A	112.00
Br1—C5—C4	120.1 (5)	C6—C7—H7B	111.00
Br1—C5—C6	118.7 (5)	C8—C7—H7A	112.00
C4—C5—C6	121.3 (6)	C8—C7—H7B	112.00
C1—C6—C5	117.8 (6)	H7A—C7—H7B	109.00
C1—C6—C7	112.1 (5)	Br2—C8—H8	108.00
C5—C6—C7	130.1 (6)	C7—C8—H8	108.00
C6—C7—C8	101.3 (5)	C9—C8—H8	108.00
Br2—C8—C7	112.1 (4)	O1—C9—H9	112.00
Br2—C8—C9	113.7 (4)	C1—C9—H9	112.00
C7—C8—C9	107.2 (5)	C8—C9—H9	112.00
O1—C9—C1	106.8 (4)	C10—C11—H11A	109.00
O1—C9—C8	111.9 (5)	C10—C11—H11B	109.00
C1—C9—C8	101.4 (5)	C10—C11—H11C	109.00
O1—C10—O2	124.1 (6)	H11A—C11—H11B	109.00
O1—C10—C11	110.8 (6)	H11A—C11—H11C	109.00
O2—C10—C11	125.0 (7)	H11B—C11—H11C	109.00
C9—O1—C10—C11	−170.2 (6)	C2—C3—C4—C5	−0.4 (11)
C10—O1—C9—C1	−150.4 (5)	C3—C4—C5—C6	0.1 (10)
C10—O1—C9—C8	99.5 (6)	C3—C4—C5—Br1	179.5 (5)
C9—O1—C10—O2	10.3 (9)	Br1—C5—C6—C7	−0.3 (9)
C9—C1—C2—C3	−177.0 (6)	C4—C5—C6—C1	1.4 (9)
C2—C1—C6—C5	−2.7 (9)	C4—C5—C6—C7	179.2 (6)
C2—C1—C6—C7	179.2 (5)	Br1—C5—C6—C1	−178.0 (4)
C6—C1—C2—C3	2.5 (9)	C1—C6—C7—C8	−15.9 (7)
C6—C1—C9—O1	−99.5 (6)	C5—C6—C7—C8	166.3 (6)
C6—C1—C9—C8	17.8 (6)	C6—C7—C8—Br2	152.3 (4)
C2—C1—C9—O1	80.1 (7)	C6—C7—C8—C9	26.7 (6)
C9—C1—C6—C5	176.8 (5)	Br2—C8—C9—C1	−152.1 (4)
C9—C1—C6—C7	−1.3 (7)	C7—C8—C9—O1	86.0 (6)
C2—C1—C9—C8	−162.7 (6)	C7—C8—C9—C1	−27.5 (6)
C1—C2—C3—C4	−0.8 (10)	Br2—C8—C9—O1	−38.6 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O2	0.98	2.36	2.704 (8)	100