PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o1928.
Published online 2010 July 7. doi:  10.1107/S1600536810025766
PMCID: PMC3007543

2,5-Dihy­droxy­terephthalic acid dihydrate

Abstract

The title compound, C8H6O6·2H2O, was obtained by accident within a project on the synthesis of metal–organic coordination polymers by the reaction of LiOH with 2,5-dihy­droxy­terephthalic acid under solvothermal conditions. The asymmetric unit consists of half a 2,5-dihy­droxy­terephthalic acid mol­ecule located on a centre of inversion and one solvent water mol­ecule that occupies a general position. The 2,5-dihy­droxy­terephthalic acid mol­ecules are connected to the water mol­ecules via O—H(...)O hydrogen bonding to form a layer in the ab plane.

Related literature

For genernal background to supramolecular assembly and crystal engineering, see: Kitagawa et al. (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1928-scheme1.jpg

Experimental

Crystal data

  • C8H6O6·2H2O
  • M r = 234.16
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1928-efi1.jpg
  • a = 5.1883 (10) Å
  • b = 17.545 (4) Å
  • c = 5.4990 (12) Å
  • β = 103.03 (1)°
  • V = 487.68 (17) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.15 mm−1
  • T = 295 K
  • 0.25 × 0.20 × 0.20 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.945, T max = 0.963
  • 4475 measured reflections
  • 1208 independent reflections
  • 589 reflections with I > 2σ(I)
  • R int = 0.080

Refinement

  • R[F 2 > 2σ(F 2)] = 0.061
  • wR(F 2) = 0.193
  • S = 1.02
  • 1208 reflections
  • 73 parameters
  • H-atom parameters constrained
  • Δρmax = 0.36 e Å−3
  • Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810025766/nc2191sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025766/nc2191Isup2.hkl

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

Acknowledgments

The authors gratefully acknowledge financial support from the National Science Council, Taiwan, and also funding as a CYCU Distinctive Research Area project (grant No. CYCU-98-CR-CH).

supplementary crystallographic information

Experimental

The solvothermal reactions were carried out in Teflon-lined digestion bombs (internal volume of 23 ml) under autogenously pressure by heating the reaction mixtures followed by slow cooling at 6 K h-1 to room temperature. Crystals of the title compound were obtained from the reaction of 2,5-dihydroxyterephthalic acid (C8H4O6, 0.198 g, 1.0 mmol) with Li(OH) (0.048 g, 2.0 mmol) in H2O (10.0 ml). The mixture was heated at 363 K for 3 d. On cooling light-yellow crystals had formed.

Refinement

The H atoms of the benzene rings were placed in idealized positions and constrained to ride on their parent atoms, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C). The hydroxyl H atoms of the carboxyl groups were placed in ideal positions with the O—H bond trans to the longest bond of the adjacent atom (O—H = 0.82 Å) and refined using a riding model. One H atom of the water molecule were located in difference map, the other placed in an ideal position in order that reasonable hydrogen bonding is found. Finally they were refined using a riding model with O—H = 0.85 Å. All O—H H atoms were refined with Uiso(H) = 1.2Ueq(O).

Figures

Fig. 1.
The molecular structure view of the title compound with labelling and displacement ellipsoids drawn at the 50% probability level. [symmetry codes: (i) -x, 1 - y, 2 - z].
Fig. 2.
Crystal structure of title compound with view along a-axis. Hydrogen bonding is shown as blue dashed lines.

Crystal data

C8H6O6·2H2OF(000) = 244
Mr = 234.16Dx = 1.595 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 5.1883 (10) ÅCell parameters from 760 reflections
b = 17.545 (4) Åθ = 2.3–22.5°
c = 5.4990 (12) ŵ = 0.15 mm1
β = 103.03 (1)°T = 295 K
V = 487.68 (17) Å3Tablular, light-yellow
Z = 20.25 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer1208 independent reflections
Radiation source: fine-focus sealed tube589 reflections with I > 2σ(I)
graphiteRint = 0.080
Detector resolution: 8.3333 pixels mm-1θmax = 28.4°, θmin = 2.3°
[var phi] and ω scansh = −5→6
Absorption correction: multi-scan (SADABS; Bruker, 2009)k = −23→23
Tmin = 0.945, Tmax = 0.963l = −7→4
4475 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.193H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0851P)2] where P = (Fo2 + 2Fc2)/3
1208 reflections(Δ/σ)max = 0.009
73 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = −0.32 e Å3

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
O10.0253 (5)0.35101 (13)0.8449 (4)0.0561 (7)
H1A−0.06150.32310.91530.084*
O20.4188 (5)0.59034 (13)0.6391 (4)0.0488 (7)
H2B0.49150.62610.58570.073*
O30.2796 (5)0.68281 (14)0.8554 (4)0.0536 (7)
O1W0.6537 (4)0.69917 (13)1.4663 (4)0.0524 (7)
H1WA0.53990.72881.37960.079*
H1WB0.74860.68111.37240.079*
C10.0087 (6)0.42428 (18)0.9234 (5)0.0371 (8)
C20.1432 (6)0.48027 (18)0.8263 (5)0.0394 (9)
H2A0.23940.46710.70890.047*
C30.2843 (6)0.61572 (19)0.7961 (5)0.0378 (8)
C40.1382 (6)0.55608 (17)0.9001 (5)0.0337 (8)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0761 (17)0.0361 (15)0.0720 (15)−0.0063 (12)0.0504 (14)−0.0070 (12)
O20.0610 (15)0.0415 (15)0.0545 (14)−0.0033 (11)0.0352 (12)0.0004 (11)
O30.0678 (17)0.0402 (15)0.0639 (16)−0.0083 (12)0.0380 (13)−0.0066 (12)
O1W0.0646 (16)0.0461 (16)0.0575 (14)0.0068 (12)0.0371 (13)0.0091 (12)
C10.0391 (18)0.037 (2)0.0386 (16)0.0007 (14)0.0155 (14)−0.0015 (14)
C20.0412 (19)0.043 (2)0.0399 (17)0.0012 (15)0.0208 (15)−0.0001 (15)
C30.0377 (18)0.041 (2)0.0366 (17)−0.0011 (15)0.0131 (14)0.0051 (15)
C40.0338 (17)0.0363 (19)0.0324 (15)0.0026 (13)0.0105 (13)0.0015 (13)

Geometric parameters (Å, °)

O1—C11.365 (4)C1—C21.380 (4)
O1—H1A0.8200C1—C4i1.405 (4)
O2—C31.305 (3)C2—C41.393 (4)
O2—H2B0.8200C2—H2A0.9300
O3—C31.223 (4)C3—C41.480 (4)
O1W—H1WA0.8485C4—C1i1.406 (4)
O1W—H1WB0.8511
C1—O1—H1A109.5C4—C2—H2A119.2
C3—O2—H2B109.5O3—C3—O2123.4 (3)
H1WA—O1W—H1WB108.2O3—C3—C4122.3 (3)
O1—C1—C2118.3 (3)O2—C3—C4114.3 (3)
O1—C1—C4i122.1 (3)C2—C4—C1i119.0 (3)
C2—C1—C4i119.5 (3)C2—C4—C3121.2 (3)
C1—C2—C4121.5 (3)C1i—C4—C3119.9 (3)
C1—C2—H2A119.2

Symmetry codes: (i) −x, −y+1, −z+2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1A···O3i0.821.882.597 (3)146
O2—H2B···O1Wii0.821.742.561 (3)177
O1W—H1WB···O1iii0.851.942.786 (3)175.0
O1W—H1WA···O3iv0.852.042.809 (3)150.4

Symmetry codes: (i) −x, −y+1, −z+2; (ii) x, y, z−1; (iii) −x+1, −y+1, −z+2; (iv) x, −y+3/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2191).

References

  • Bruker (2009). APEX2, SADABS and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Kitagawa, S., Kitaura, R. & Noro, S. (2004). Angew. Chem. Int. Ed.43, 2334–2338. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography