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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o3.
Published online 2007 December 6. doi:  10.1107/S1600536807062320
PMCID: PMC2914893

3,5-Dibromo-2-hydroxy­benzoic acid

Abstract

The title compound, C7H4Br2O3, has an intra­molecular O—H(...)O=C hydrogen bond and aggregates to form hydrogen-bonded dimers via O—H(...)O inter­actions. The formation of zigzag one-dimensional mol­ecular tapes via C—H(...)Br inter­actions and π–π stacking inter­actions (inter­planar separation = 3.42 Å) completes the crystal structure.

Related literature

For related literature, see: Chiari et al. (1981 [triangle]); Jin & Xiao (2005 [triangle]).

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Object name is e-64-000o3-scheme1.jpg

Experimental

Crystal data

  • C7H4Br2O3
  • M r = 295.92
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-000o3-efi1.jpg
  • a = 10.770 (3) Å
  • b = 11.082 (3) Å
  • c = 14.879 (4) Å
  • β = 105.606 (3)°
  • V = 1710.4 (8) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 9.44 mm−1
  • T = 293 (2) K
  • 0.50 × 0.31 × 0.21 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.088, T max = 0.243 (expected range = 0.050–0.138)
  • 6362 measured reflections
  • 1599 independent reflections
  • 1286 reflections with I > 2σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.031
  • wR(F 2) = 0.061
  • S = 1.79
  • 1599 reflections
  • 111 parameters
  • H-atom parameters constrained
  • Δρmax = 0.82 e Å−3
  • Δρmin = −0.81 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1998 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: SHELXTL (Bruker, 1998 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807062320/gg2052sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062320/gg2052Isup2.hkl

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

Acknowledgments

This work was supported by the National Natural Science Foundation of China (grant No. 20662007).

supplementary crystallographic information

Comment

The compound 2-hydroxybenzoic acid (salicylic acid) and its derivatives have been widely studied as medicines or important active pharmaceutical intermediates (Chiari et al., 1981; Jin & Xiao, 2005). Herein, we report the crystal structure of the title compound, (I).

In (I) (Fig. 1), the atoms O1, O2, O3, Br1, Br2, C1 and aromatic ring {C2,···,C7} are essentially coplanar with a mean deviation of 0.014 Å. The crystal packing is stabilized by intramolecular and intermolecular O—H···O and C—H···Br hydrogen bonds (Table 1).

Experimental

Crystals appropriate for data collection were obtained by recrystallization from ethanol (m.p. 500–501 K).

Refinement

The hydroxyl H atom and the carboxylate H atom were located from difference Fourier map but were refined using the riding model with O—H distance restrained to 0.82Å and Uiso(H) = 1.5Ueq(O); while all other H atoms were placed at geometrical idealized positions with C—H = 0.93Å and Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound depicted with 30% probability displacement ellipsoids.

Crystal data

C7H4Br2O3F000 = 1120
Mr = 295.92Dx = 2.298 Mg m3
Monoclinic, C2/cMelting point: 500 K
Hall symbol: -C 2ycMo Kα radiation λ = 0.71073 Å
a = 10.770 (3) ÅCell parameters from 2346 reflections
b = 11.082 (3) Åθ = 2.7–26.3º
c = 14.879 (4) ŵ = 9.44 mm1
β = 105.606 (3)ºT = 293 (2) K
V = 1710.4 (8) Å3Block, light-yellow
Z = 80.50 × 0.31 × 0.21 mm

Data collection

Bruker SMART CCD diffractometer1599 independent reflections
Radiation source: fine-focus sealed tube1286 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.032
T = 293(2) Kθmax = 25.5º
[var phi] and ω scansθmin = 2.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −13→13
Tmin = 0.088, Tmax = 0.243k = −13→13
6362 measured reflectionsl = −17→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.061  w = 1/[σ2(Fo2)] where P = (Fo2 + 2Fc2)/3
S = 1.79(Δ/σ)max = 0.001
1599 reflectionsΔρmax = 0.82 e Å3
111 parametersΔρmin = −0.81 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

xyzUiso*/Ueq
Br11.06441 (4)0.35585 (3)0.42603 (3)0.07017 (19)
Br20.68570 (4)0.02983 (4)0.22295 (3)0.05891 (17)
O11.2480 (2)−0.0861 (2)0.49804 (18)0.0543 (7)
H11.2875−0.14640.52190.081*
O21.1105 (2)−0.2248 (2)0.41973 (16)0.0545 (7)
O30.8866 (2)−0.1506 (2)0.31093 (18)0.0560 (7)
H30.9422−0.20050.33410.084*
C11.1390 (3)−0.1185 (3)0.4393 (2)0.0422 (9)
C21.0523 (3)−0.0171 (3)0.3998 (2)0.0376 (8)
C31.0907 (3)0.1018 (3)0.4246 (2)0.0403 (9)
H3A1.17120.11720.46540.048*
C41.0092 (3)0.1959 (3)0.3885 (2)0.0412 (9)
C50.8890 (3)0.1766 (3)0.3280 (2)0.0414 (9)
H50.83490.24100.30400.050*
C60.8509 (3)0.0593 (3)0.3040 (2)0.0395 (9)
C70.9306 (3)−0.0390 (3)0.3386 (2)0.0387 (8)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0482 (3)0.0329 (2)0.1040 (4)−0.00311 (18)−0.0233 (2)0.0025 (2)
Br20.0371 (2)0.0526 (3)0.0726 (3)−0.00593 (18)−0.0101 (2)−0.0044 (2)
O10.0511 (16)0.0353 (14)0.0606 (17)0.0064 (12)−0.0126 (13)0.0036 (12)
O20.0583 (17)0.0327 (15)0.0596 (17)0.0041 (12)−0.0064 (13)−0.0017 (12)
O30.0514 (16)0.0348 (15)0.0690 (18)−0.0019 (12)−0.0056 (13)−0.0074 (13)
C10.039 (2)0.043 (2)0.041 (2)0.0019 (17)0.0051 (17)0.0040 (17)
C20.040 (2)0.033 (2)0.037 (2)0.0013 (16)0.0032 (17)0.0044 (15)
C30.0332 (19)0.037 (2)0.043 (2)−0.0024 (16)−0.0032 (16)0.0013 (16)
C40.041 (2)0.0296 (19)0.047 (2)−0.0045 (15)0.0024 (18)0.0026 (16)
C50.0325 (19)0.036 (2)0.050 (2)0.0017 (16)0.0011 (17)0.0028 (17)
C60.0326 (19)0.041 (2)0.041 (2)−0.0032 (16)0.0026 (16)−0.0023 (16)
C70.042 (2)0.035 (2)0.037 (2)−0.0032 (17)0.0082 (17)−0.0017 (16)

Geometric parameters (Å, °)

Br1—C41.905 (3)C2—C31.401 (4)
Br2—C61.890 (3)C2—C71.402 (5)
O1—C11.311 (4)C3—C41.375 (5)
O1—H10.8200C3—H3A0.9300
O2—C11.233 (4)C4—C51.381 (5)
O3—C71.348 (4)C5—C61.380 (4)
O3—H30.8200C5—H50.9300
C1—C21.478 (5)C6—C71.397 (5)
C1—O1—H1109.5C3—C4—Br1118.3 (3)
C7—O3—H3109.5C5—C4—Br1119.9 (3)
O2—C1—O1122.7 (3)C6—C5—C4118.4 (3)
O2—C1—C2122.9 (3)C6—C5—H5120.8
O1—C1—C2114.4 (3)C4—C5—H5120.8
C3—C2—C7119.5 (3)C5—C6—C7122.0 (3)
C3—C2—C1120.0 (3)C5—C6—Br2119.4 (3)
C7—C2—C1120.4 (3)C7—C6—Br2118.6 (3)
C4—C3—C2119.9 (3)O3—C7—C6118.2 (3)
C4—C3—H3A120.1O3—C7—C2123.2 (3)
C2—C3—H3A120.1C6—C7—C2118.5 (3)
C3—C4—C5121.7 (3)
O2—C1—C2—C3−179.7 (3)C4—C5—C6—C7−0.5 (5)
O1—C1—C2—C31.3 (5)C4—C5—C6—Br2179.0 (3)
O2—C1—C2—C71.2 (6)C5—C6—C7—O3−179.3 (3)
O1—C1—C2—C7−177.8 (3)Br2—C6—C7—O31.2 (4)
C7—C2—C3—C4−0.3 (5)C5—C6—C7—C20.5 (5)
C1—C2—C3—C4−179.3 (3)Br2—C6—C7—C2−179.0 (2)
C2—C3—C4—C50.2 (5)C3—C2—C7—O3179.7 (3)
C2—C3—C4—Br1178.9 (2)C1—C2—C7—O3−1.2 (5)
C3—C4—C5—C60.2 (5)C3—C2—C7—C6−0.1 (5)
Br1—C4—C5—C6−178.5 (2)C1—C2—C7—C6179.0 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.821.872.684 (3)175
O3—H3···O20.821.932.648 (3)145
C3—H3A···Br1ii0.932.893.810 (3)172

Symmetry codes: (i) −x+5/2, −y−1/2, −z+1; (ii) −x+5/2, −y+1/2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GG2052).

References

  • Bruker (1998). SHELXTL, SAINT and SMART (Version 5.0). Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chiari, G., Fronczek, F. R., Davis, S. T. & Gandour, R. D. (1981). Acta Cryst. B37, 1623–1625.
  • Jin, L.-F. & Xiao, F.-P. (2005). Acta Cryst. E61, o1198–o1199.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.

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