organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

2,5-Dihy­dr­oxy­terephthalic acid dihydrate

aDepartment of Chemistry, Chung-Yuan Christian University, Chung-Li 320, Taiwan
*Correspondence e-mail: chiaher@cycu.edu.tw

(Received 25 June 2010; accepted 30 June 2010; online 7 July 2010)

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[Kitagawa, S., Kitaura, R. & Noro, S. (2004). Angew. Chem. Int. Ed. 43, 2334-2338. ]).

[Scheme 1]

Experimental

Crystal data
  • C8H6O6·2H2O

  • Mr = 234.16

  • Monoclinic, P 21 /c

  • 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[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.945, Tmax = 0.963

  • 4475 measured reflections

  • 1208 independent reflections

  • 589 reflections with I > 2σ(I)

  • Rint = 0.080

Refinement
  • R[F2 > 2σ(F2)] = 0.061

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1A⋯O3i 0.82 1.88 2.597 (3) 146
O2—H2B⋯O1Wii 0.82 1.74 2.561 (3) 177
O1W—H1WB⋯O1iii 0.85 1.94 2.786 (3) 175.0
O1W—H1WA⋯O3iv 0.85 2.04 2.809 (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+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Related literature top

For background, see: Kitagawa et al. (2004).

Experimental top

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 top

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).

Structure description top

For background, see: Kitagawa et al. (2004).

Computing details top

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

Figures top
[Figure 1] 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].
[Figure 2] Fig. 2. Crystal structure of title compound with view along a-axis. Hydrogen bonding is shown as blue dashed lines.
2,5-dihydroxybenzene-1,4-dicarboxylic acid dihydrate top
Crystal data top
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 top
Bruker APEXII CCD
diffractometer
1208 independent reflections
Radiation source: fine-focus sealed tube589 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.080
Detector resolution: 8.3333 pixels mm-1θmax = 28.4°, θmin = 2.3°
φ and ω scansh = 56
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 2323
Tmin = 0.945, Tmax = 0.963l = 74
4475 measured 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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.193H-atom parameters constrained
S = 1.02 w = 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
Crystal data top
C8H6O6·2H2OV = 487.68 (17) Å3
Mr = 234.16Z = 2
Monoclinic, P21/cMo Kα radiation
a = 5.1883 (10) ŵ = 0.15 mm1
b = 17.545 (4) ÅT = 295 K
c = 5.4990 (12) Å0.25 × 0.20 × 0.20 mm
β = 103.03 (1)°
Data collection top
Bruker APEXII CCD
diffractometer
1208 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
589 reflections with I > 2σ(I)
Tmin = 0.945, Tmax = 0.963Rint = 0.080
4475 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0610 restraints
wR(F2) = 0.193H-atom parameters constrained
S = 1.02Δρmax = 0.36 e Å3
1208 reflectionsΔρmin = 0.32 e Å3
73 parameters
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
O10.0253 (5)0.35101 (13)0.8449 (4)0.0561 (7)
H1A0.06150.32310.91530.084*
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) top
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, º) top
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 code: (i) x, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
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, z1; (iii) x+1, y+1, z+2; (iv) x, y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC8H6O6·2H2O
Mr234.16
Crystal system, space groupMonoclinic, P21/c
Temperature (K)295
a, b, c (Å)5.1883 (10), 17.545 (4), 5.4990 (12)
β (°) 103.03 (1)
V3)487.68 (17)
Z2
Radiation typeMo Kα
µ (mm1)0.15
Crystal size (mm)0.25 × 0.20 × 0.20
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.945, 0.963
No. of measured, independent and
observed [I > 2σ(I)] reflections
4475, 1208, 589
Rint0.080
(sin θ/λ)max1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.193, 1.02
No. of reflections1208
No. of parameters73
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.36, 0.32

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O3i0.821.882.597 (3)146.0
O2—H2B···O1Wii0.821.742.561 (3)177.4
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, z1; (iii) x+1, y+1, z+2; (iv) x, y+3/2, z+1/2.
 

Acknowledgements

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).

References

First citationBruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationKitagawa, S., Kitaura, R. & Noro, S. (2004). Angew. Chem. Int. Ed. 43, 2334–2338.   Web of Science CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
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