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Single crystals of 2-bromo­fumaric acid, C4H3BrO4, were obtained from an aqueous solution of racemic 2,3-dibromo­succinic acid and (−)-quinine. The title compound crystallizes with two mol­ecules in the asymmetric unit. The structure is stabilized by O—H...O hydrogen bonds forming alternating chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680603368X/sj2110sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680603368X/sj2110Isup2.hkl
Contains datablock I

CCDC reference: 621507

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.037
  • wR factor = 0.072
  • Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.42 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.44 PLAT701_ALERT_1_C Bond Calc 1.865(3), Rep 1.861(3), Dev.. 1.33 Sigma BR1 -C2 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: maXus (Mackay et al., 1999).

2-Bromofumaric acid top
Crystal data top
C4H3BrO4Z = 4
Mr = 194.97F(000) = 376
Triclinic, P1Dx = 2.188 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.8290 (4) ÅCell parameters from 60 reflections
b = 8.3791 (4) Åθ = 4.3–22.0°
c = 10.2443 (3) ŵ = 6.88 mm1
α = 69.572 (4)°T = 299 K
β = 70.383 (3)°Fragment, colourless
γ = 79.963 (4)°0.30 × 0.30 × 0.30 mm
V = 591.97 (5) Å3
Data collection top
Bruker Nonius KappaCCD area-detector
diffractometer
1821 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.052
φ and ω scansθmax = 27.5°, θmin = 4.5°
Absorption correction: numerical
(Herrendorf & Bärnighausen, 1997)
h = 1010
Tmin = 0.581, Tmax = 0.661k = 1010
11936 measured reflectionsl = 1312
2701 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.072 w = 1/[σ2(Fo2) + (0.0231P)2 + 0.495P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2701 reflectionsΔρmax = 0.33 e Å3
167 parametersΔρmin = 0.44 e Å3
0 restraints
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br20.65543 (6)0.05029 (6)0.59519 (4)0.06076 (16)
Br10.56894 (5)0.50250 (5)0.68940 (4)0.05132 (14)
O80.7533 (4)0.1438 (3)0.2636 (3)0.0534 (7)
C20.4980 (4)0.3307 (4)0.8676 (3)0.0342 (8)
C40.2319 (5)0.2437 (5)0.8299 (4)0.0372 (8)
O70.9082 (4)0.3746 (4)0.1279 (3)0.0559 (7)
C80.8514 (5)0.2514 (5)0.2480 (4)0.0402 (8)
C30.3572 (4)0.2377 (4)0.9116 (4)0.0358 (8)
O60.8979 (3)0.1258 (3)0.7387 (2)0.0482 (7)
O40.1034 (4)0.1408 (4)0.9054 (3)0.0553 (7)
O10.7273 (4)0.4053 (3)0.9363 (3)0.0523 (7)
C50.9442 (5)0.2002 (5)0.6086 (4)0.0369 (8)
C60.8569 (5)0.1816 (4)0.5055 (4)0.0369 (8)
O20.5820 (4)0.1726 (4)1.0752 (3)0.0620 (8)
C70.9219 (5)0.2552 (5)0.3632 (4)0.0393 (8)
O51.0728 (4)0.3031 (4)0.5434 (3)0.0639 (8)
C10.6154 (5)0.3058 (5)0.9637 (4)0.0376 (8)
O30.2492 (4)0.3336 (4)0.7044 (3)0.0615 (8)
H7O0.86240.37200.06750.084*
H30.32960.15371.00680.043*
H40.04090.14320.85450.083*
H20.64740.16551.12530.093*
H71.02730.31660.33770.047*
H51.12560.30060.60110.096*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br20.0524 (3)0.0857 (4)0.0506 (2)0.0289 (2)0.01035 (19)0.0224 (2)
Br10.0495 (2)0.0573 (3)0.0433 (2)0.01669 (19)0.01746 (18)0.00144 (18)
O80.0680 (18)0.0545 (17)0.0518 (15)0.0154 (15)0.0354 (14)0.0115 (13)
C20.0372 (19)0.040 (2)0.0298 (16)0.0034 (16)0.0118 (15)0.0135 (15)
C40.0379 (19)0.043 (2)0.0383 (19)0.0073 (17)0.0154 (16)0.0160 (17)
O70.0632 (18)0.076 (2)0.0339 (13)0.0234 (15)0.0233 (13)0.0058 (14)
C80.038 (2)0.050 (2)0.039 (2)0.0019 (18)0.0176 (16)0.0172 (18)
C30.0385 (19)0.039 (2)0.0351 (17)0.0064 (16)0.0147 (15)0.0124 (15)
O60.0477 (15)0.0671 (18)0.0335 (13)0.0155 (13)0.0165 (11)0.0104 (12)
O40.0502 (16)0.0739 (19)0.0502 (15)0.0276 (15)0.0230 (13)0.0106 (14)
O10.0561 (16)0.0621 (18)0.0481 (14)0.0235 (14)0.0271 (13)0.0080 (13)
C50.0360 (19)0.044 (2)0.0365 (18)0.0016 (17)0.0176 (16)0.0139 (16)
C60.0355 (19)0.040 (2)0.0421 (19)0.0028 (16)0.0172 (16)0.0158 (16)
O20.084 (2)0.0598 (19)0.0561 (17)0.0280 (16)0.0477 (16)0.0023 (14)
C70.040 (2)0.049 (2)0.0375 (19)0.0053 (17)0.0203 (16)0.0136 (17)
O50.074 (2)0.087 (2)0.0383 (14)0.0440 (18)0.0270 (14)0.0014 (14)
C10.040 (2)0.043 (2)0.0349 (18)0.0065 (17)0.0130 (15)0.0149 (16)
O30.0688 (19)0.077 (2)0.0478 (16)0.0343 (16)0.0315 (14)0.0025 (15)
Geometric parameters (Å, º) top
Br2—C61.860 (3)O1—C11.210 (4)
Br1—C21.861 (3)C5—O51.284 (4)
O8—C81.217 (4)C5—C61.497 (4)
C2—C31.320 (4)C6—C71.321 (5)
C2—C11.500 (4)O2—C11.274 (4)
C4—O31.216 (4)O7—H7O0.8200
C4—O41.290 (4)C3—H30.9600
C4—C31.472 (4)O4—H40.8200
O7—C81.295 (4)O2—H20.8200
C8—C71.472 (4)C7—H70.9601
O6—C51.212 (4)O5—H50.8200
C3—C2—C1120.9 (3)C7—C6—Br2124.7 (3)
C3—C2—Br1125.3 (2)C5—C6—Br2114.5 (2)
C1—C2—Br1113.8 (2)C6—C7—C8127.6 (3)
O3—C4—O4123.7 (3)O1—C1—O2124.9 (3)
O3—C4—C3123.8 (3)O1—C1—C2122.1 (3)
O4—C4—C3112.5 (3)O2—C1—C2112.9 (3)
O8—C8—O7124.3 (3)C8—O7—H7O109.5
O8—C8—C7123.9 (3)C2—C3—H3119.2
O7—C8—C7111.9 (3)C4—C3—H3113.2
C2—C3—C4127.5 (3)C4—O4—H4109.5
O6—C5—O5124.3 (3)C1—O2—H2109.5
O6—C5—C6123.3 (3)C6—C7—H7112.5
O5—C5—C6112.4 (3)C8—C7—H7119.9
C7—C6—C5120.8 (3)C5—O5—H5109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O7—H7O···O1i0.821.892.702 (3)168
O4—H4···O6ii0.821.932.752 (3)175
O2—H2···O8iii0.821.812.621 (3)169
O5—H5···O3iv0.821.762.574 (3)170
Symmetry codes: (i) x, y, z1; (ii) x1, y, z; (iii) x, y, z+1; (iv) x+1, y, z.
 

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