2,3-Dibromo-3-phenyl-propionic acid.

In the crystal of the title compound, C(9)H(8)Br(2)O(2), inversion dimers linked by two O-H⋯O hydrogen bonds occur. All of the carbon and oxygen atoms are disordered over two sets of sites in a 2:1 ratio.

Related literature

For threo-1,2-diphenyl-2,3-difluoro­propionate, see: O’Hagan et al. (2006 ▶). For R-methyl 3-bromo-2-chloro-3-phenyl­propionate, see: Shaw et al. (1995 ▶).

Experimental

Crystal data

C9H8Br2O2

M = 307.97

Orthorhombic,

a = 7.0278 (1) Å

b = 9.7105 (1) Å

c = 29.2970 (4) Å

V = 1999.33 (4) Å3

Z = 8

Mo Kα radiation

μ = 8.07 mm−1

T = 100 (2) K

0.28 × 0.22 × 0.14 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.211, T max = 0.398 (expected range = 0.171–0.323)

17420 measured reflections

2303 independent reflections

2056 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.066

S = 1.06

2303 reflections

127 parameters

83 restraints

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −0.62 e Å−3

Data collection: APEX2 (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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802919X/tk2304sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802919X/tk2304Isup2.hkl

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

C9H8Br2O2	F(000) = 1184
Mr = 307.97	Dx = 2.046 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8127 reflections
a = 7.0278 (1) Å	θ = 2.2–28.2°
b = 9.7105 (1) Å	µ = 8.07 mm−1
c = 29.2970 (4) Å	T = 100 K
V = 1999.33 (4) Å3	Block, colorless
Z = 8	0.28 × 0.22 × 0.14 mm

Bruker SMART APEX diffractometer	2303 independent reflections
Radiation source: fine-focus sealed tube	2056 reflections with I > 2σ(I)
graphite	Rint = 0.027
ω scans	θmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.211, Tmax = 0.398	k = −12→12
17420 measured reflections	l = −37→38

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0337P)2 + 3.2334P] where P = (Fo2 + 2Fc2)/3
2303 reflections	(Δ/σ)max = 0.001
127 parameters	Δρmax = 0.61 e Å−3
83 restraints	Δρmin = −0.62 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1	0.48392 (4)	0.31033 (3)	0.364350 (9)	0.02208 (9)
Br2	−0.06355 (4)	0.45596 (3)	0.436758 (9)	0.03094 (10)
O1	0.4216 (6)	0.3279 (4)	0.48256 (13)	0.0308 (10)	0.67
H1O	0.4765	0.3569	0.5061	0.046*	0.67
O2	0.4214 (10)	0.5338 (5)	0.4476 (3)	0.0209 (10)	0.67
C1	0.3847 (4)	0.4118 (4)	0.44922 (12)	0.0189 (8)	0.67
C2	0.2859 (5)	0.3388 (4)	0.40959 (12)	0.0176 (7)	0.67
H2	0.2344	0.2480	0.4200	0.021*	0.67
C3	0.1313 (5)	0.4223 (4)	0.38839 (12)	0.0183 (7)	0.67
H3	0.1859	0.5130	0.3790	0.022*	0.67
C4	0.0358 (4)	0.3575 (5)	0.34721 (14)	0.0133 (8)	0.67
C5	−0.0307 (8)	0.2228 (5)	0.3486 (3)	0.0186 (11)	0.67
H5	−0.0167	0.1697	0.3756	0.022*	0.67
C6	−0.1176 (9)	0.1657 (9)	0.3104 (4)	0.0224 (6)	0.67
H6	−0.1631	0.0736	0.3114	0.027*	0.67
C7	−0.1381 (9)	0.2433 (15)	0.2709 (3)	0.0181 (8)	0.67
H7	−0.1976	0.2043	0.2448	0.022*	0.67
C8	−0.0716 (13)	0.3781 (14)	0.26947 (16)	0.0206 (7)	0.67
H8	−0.0856	0.4311	0.2424	0.025*	0.67
C9	0.0154 (11)	0.4352 (8)	0.3076 (2)	0.0183 (9)	0.67
H9	0.0608	0.5273	0.3067	0.022*	0.67
O1'	0.3463 (14)	0.3474 (10)	0.4912 (3)	0.0308 (10)	0.33
H1'O	0.4202	0.3715	0.5122	0.046*	0.33
O2'	0.380 (2)	0.5445 (11)	0.4542 (7)	0.0209 (10)	0.33
C1'	0.3118 (9)	0.4305 (9)	0.4576 (2)	0.0189 (8)	0.33
C2'	0.1737 (9)	0.3684 (7)	0.4228 (2)	0.0176 (7)	0.33
H2'	0.1633	0.2666	0.4274	0.021*	0.33
C3'	0.2239 (9)	0.3993 (8)	0.3748 (2)	0.0183 (7)	0.33
H3'	0.2355	0.5012	0.3709	0.022*	0.33
C4'	0.0862 (9)	0.3432 (12)	0.3394 (3)	0.0133 (8)	0.33
C5'	0.0090 (19)	0.2117 (12)	0.3425 (6)	0.0186 (11)	0.33
H5'	0.0421	0.1536	0.3674	0.022*	0.33
C6'	−0.1164 (19)	0.165 (2)	0.3092 (8)	0.0224 (6)	0.33
H6'	−0.1692	0.0754	0.3113	0.027*	0.33
C7'	−0.1648 (18)	0.250 (3)	0.2729 (6)	0.0181 (8)	0.33
H7'	−0.2505	0.2185	0.2501	0.022*	0.33
C8'	−0.088 (3)	0.382 (3)	0.2698 (4)	0.0206 (7)	0.33
H8'	−0.1207	0.4398	0.2449	0.025*	0.33
C9'	0.038 (2)	0.4282 (17)	0.3031 (5)	0.0183 (9)	0.33
H9'	0.0906	0.5181	0.3010	0.022*	0.33

	U11	U22	U33	U12	U13	U23
Br1	0.02081 (14)	0.02271 (15)	0.02272 (15)	−0.00251 (10)	−0.00187 (10)	−0.00479 (10)
Br2	0.03118 (17)	0.04015 (19)	0.02150 (15)	0.00134 (13)	0.00331 (11)	−0.00921 (12)
O1	0.055 (3)	0.0188 (16)	0.0182 (18)	−0.0063 (19)	−0.0143 (18)	0.0006 (13)
O2	0.034 (3)	0.0169 (12)	0.012 (3)	0.0006 (16)	−0.0033 (18)	−0.0032 (12)
C1	0.023 (2)	0.0199 (18)	0.0139 (17)	−0.0030 (19)	−0.0010 (16)	−0.0003 (14)
C2	0.0211 (17)	0.0149 (15)	0.0166 (16)	−0.0017 (14)	0.0007 (13)	−0.0010 (12)
C3	0.021 (2)	0.0159 (16)	0.0175 (17)	−0.0033 (15)	0.0002 (14)	−0.0028 (13)
C4	0.007 (2)	0.0153 (17)	0.017 (2)	0.0062 (19)	0.0015 (16)	−0.0077 (14)
C5	0.016 (3)	0.0174 (16)	0.023 (3)	0.0023 (17)	−0.002 (2)	−0.0009 (15)
C6	0.0180 (12)	0.0183 (13)	0.0310 (15)	−0.0018 (10)	−0.0052 (11)	−0.0067 (11)
C7	0.009 (2)	0.0239 (19)	0.0215 (14)	0.006 (2)	−0.0035 (16)	−0.0106 (11)
C8	0.0169 (19)	0.0259 (15)	0.0190 (12)	0.0082 (15)	0.0007 (11)	−0.0025 (10)
C9	0.017 (2)	0.0167 (14)	0.0211 (18)	0.0027 (13)	0.0015 (14)	−0.0037 (14)
O1'	0.055 (3)	0.0188 (16)	0.0182 (18)	−0.0063 (19)	−0.0143 (18)	0.0006 (13)
O2'	0.034 (3)	0.0169 (12)	0.012 (3)	0.0006 (16)	−0.0033 (18)	−0.0032 (12)
C1'	0.023 (2)	0.0199 (18)	0.0139 (17)	−0.0030 (19)	−0.0010 (16)	−0.0003 (14)
C2'	0.0211 (17)	0.0149 (15)	0.0166 (16)	−0.0017 (14)	0.0007 (13)	−0.0010 (12)
C3'	0.021 (2)	0.0159 (16)	0.0175 (17)	−0.0033 (15)	0.0002 (14)	−0.0028 (13)
C4'	0.007 (2)	0.0153 (17)	0.017 (2)	0.0062 (19)	0.0015 (16)	−0.0077 (14)
C5'	0.016 (3)	0.0174 (16)	0.023 (3)	0.0023 (17)	−0.002 (2)	−0.0009 (15)
C6'	0.0180 (12)	0.0183 (13)	0.0310 (15)	−0.0018 (10)	−0.0052 (11)	−0.0067 (11)
C7'	0.009 (2)	0.0239 (19)	0.0215 (14)	0.006 (2)	−0.0035 (16)	−0.0106 (11)
C8'	0.0169 (19)	0.0259 (15)	0.0190 (12)	0.0082 (15)	0.0007 (11)	−0.0025 (10)
C9'	0.017 (2)	0.0167 (14)	0.0211 (18)	0.0027 (13)	0.0015 (14)	−0.0037 (14)

Br1—C2	1.942 (4)	C8—H8	0.9500
Br1—C3'	2.044 (6)	C9—H9	0.9500
Br2—C2'	1.916 (6)	O1'—C1'	1.295 (8)
Br2—C3	1.997 (3)	O1'—H1'O	0.8400
O1—C1	1.298 (4)	O2'—C1'	1.212 (8)
O1—H1O	0.8400	C1'—C2'	1.533 (8)
O2—C1	1.213 (5)	C2'—C3'	1.480 (7)
C1—C2	1.527 (5)	C2'—H2'	1.0000
C2—C3	1.491 (5)	C3'—C4'	1.518 (7)
C2—H2	1.0000	C3'—H3'	1.0000
C3—C4	1.517 (4)	C4'—C5'	1.3900
C3—H3	1.0000	C4'—C9'	1.3900
C4—C5	1.3900	C5'—C6'	1.3900
C4—C9	1.3900	C5'—H5'	0.9500
C5—C6	1.3900	C6'—C7'	1.3900
C5—H5	0.9500	C6'—H6'	0.9500
C6—C7	1.3900	C7'—C8'	1.3900
C6—H6	0.9500	C7'—H7'	0.9500
C7—C8	1.3900	C8'—C9'	1.3900
C7—H7	0.9500	C8'—H8'	0.9500
C8—C9	1.3900	C9'—H9'	0.9500
C1—O1—H1O	120.0	C1'—O1'—H1'O	120.0
O2—C1—O1	126.8 (6)	O2'—C1'—O1'	124.0 (13)
O2—C1—C2	121.4 (6)	O2'—C1'—C2'	123.8 (13)
O1—C1—C2	111.8 (4)	O1'—C1'—C2'	112.3 (8)
C3—C2—C1	113.3 (3)	C3'—C2'—C1'	113.7 (6)
C3—C2—Br1	108.4 (2)	C3'—C2'—Br2	108.7 (4)
C1—C2—Br1	105.0 (2)	C1'—C2'—Br2	103.5 (4)
C3—C2—H2	110.0	C3'—C2'—H2'	110.2
C1—C2—H2	110.0	C1'—C2'—H2'	110.2
Br1—C2—H2	110.0	Br2—C2'—H2'	110.2
C2—C3—C4	115.4 (3)	C2'—C3'—C4'	115.0 (6)
C2—C3—Br2	107.0 (2)	C2'—C3'—Br1	105.6 (4)
C4—C3—Br2	109.20 (19)	C4'—C3'—Br1	108.5 (4)
C2—C3—H3	108.3	C2'—C3'—H3'	109.2
C4—C3—H3	108.3	C4'—C3'—H3'	109.2
Br2—C3—H3	108.3	Br1—C3'—H3'	109.2
C5—C4—C9	120.0	C5'—C4'—C9'	120.0
C5—C4—C3	121.0 (5)	C5'—C4'—C3'	122.3 (11)
C9—C4—C3	119.0 (5)	C9'—C4'—C3'	117.7 (11)
C4—C5—C6	120.0	C4'—C5'—C6'	120.0
C4—C5—H5	120.0	C4'—C5'—H5'	120.0
C6—C5—H5	120.0	C6'—C5'—H5'	120.0
C7—C6—C5	120.0	C7'—C6'—C5'	120.0
C7—C6—H6	120.0	C7'—C6'—H6'	120.0
C5—C6—H6	120.0	C5'—C6'—H6'	120.0
C6—C7—C8	120.0	C6'—C7'—C8'	120.0
C6—C7—H7	120.0	C6'—C7'—H7'	120.0
C8—C7—H7	120.0	C8'—C7'—H7'	120.0
C7—C8—C9	120.0	C7'—C8'—C9'	120.0
C7—C8—H8	120.0	C7'—C8'—H8'	120.0
C9—C8—H8	120.0	C9'—C8'—H8'	120.0
C8—C9—C4	120.0	C8'—C9'—C4'	120.0
C8—C9—H9	120.0	C8'—C9'—H9'	120.0
C4—C9—H9	120.0	C4'—C9'—H9'	120.0
O2—C1—C2—C3	−40.3 (4)	O2'—C1'—C2'—Br2	−77.8 (5)
O1—C1—C2—C3	140.0 (3)	O1'—C1'—C2'—Br2	102.1 (5)
O2—C1—C2—Br1	77.8 (3)	C3—Br2—C2'—C3'	0.9 (4)
O1—C1—C2—Br1	−101.9 (2)	C3—Br2—C2'—C1'	122.1 (7)
C1—C2—C3—C4	176.8 (3)	C1'—C2'—C3'—C4'	−178.0 (6)
Br1—C2—C3—C4	60.7 (4)	Br2—C2'—C3'—C4'	−63.3 (7)
C1—C2—C3—Br2	−61.5 (3)	C1'—C2'—C3'—Br1	62.4 (6)
Br1—C2—C3—Br2	−177.59 (16)	Br2—C2'—C3'—Br1	177.1 (3)
C2—C3—C4—C5	49.8 (4)	C2—Br1—C3'—C2'	0.1 (3)
Br2—C3—C4—C5	−70.8 (3)	C2—Br1—C3'—C4'	−123.7 (8)
C2—C3—C4—C9	−130.2 (4)	C2'—C3'—C4'—C5'	−42.3 (8)
Br2—C3—C4—C9	109.2 (3)	Br1—C3'—C4'—C5'	75.6 (6)
C9—C4—C5—C6	0.0	C2'—C3'—C4'—C9'	137.7 (8)
C3—C4—C5—C6	−179.99 (8)	Br1—C3'—C4'—C9'	−104.3 (6)
C4—C5—C6—C7	0.0	C9'—C4'—C5'—C6'	0.0
C5—C6—C7—C8	0.0	C3'—C4'—C5'—C6'	−179.96 (9)
C6—C7—C8—C9	0.0	C4'—C5'—C6'—C7'	0.0
C7—C8—C9—C4	0.0	C5'—C6'—C7'—C8'	0.0
C5—C4—C9—C8	0.0	C6'—C7'—C8'—C9'	0.0
C3—C4—C9—C8	179.99 (8)	C7'—C8'—C9'—C4'	0.0
O2'—C1'—C2'—C3'	40.0 (6)	C5'—C4'—C9'—C8'	0.0
O1'—C1'—C2'—C3'	−140.1 (6)	C3'—C4'—C9'—C8'	179.96 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O2i	0.84	1.86	2.68 (1)	165
O1'—H1'o···O2i	0.84	1.86	2.69 (1)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯O2i	0.84	1.86	2.68 (1)	165
O1′—H1′o⋯O2i	0.84	1.86	2.69 (1)	166

Symmetry code: (i) .