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Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): o835.
Published online 2009 March 25. doi:  10.1107/S1600536809009970
PMCID: PMC2968855

Butane-1,2,3,4-tetra­carboxylic acid dihydrate

Abstract

The asymmetric unit of the title compound, C8H10O8·2H2O, contains one half-mol­ecule of butane-1,2,3,4-tetra­carboxylic acid and a water mol­ecule, with the complete tetra-acid generated by crystallographic inversion symmetry. Inter­molecular O—H(...)O hydrogen bonds form an extensive three-dimensional network, which consolidates the crystal packing.

Related literature

For applications of butane-1,2,3,4-tetra­carboxylic acid in metal -organic coordination polymers, see: Delgado et al. (2007 [triangle]); Liu et al. (2008 [triangle]). For related crystal structures, see: McKee et al. (2007 [triangle]); Najafpour et al. (2008 [triangle]).

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Object name is e-65-0o835-scheme1.jpg

Experimental

Crystal data

  • C8H10O8·2H2O
  • M r = 270.19
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o835-efi1.jpg
  • a = 7.4668 (15) Å
  • b = 9.3385 (19) Å
  • c = 8.8406 (18) Å
  • β = 109.60 (3)°
  • V = 580.7 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.15 mm−1
  • T = 293 K
  • 0.55 × 0.46 × 0.26 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.921, T max = 0.965
  • 5478 measured reflections
  • 1327 independent reflections
  • 960 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.116
  • S = 1.17
  • 1327 reflections
  • 82 parameters
  • H-atom parameters constrained
  • Δρmax = 0.26 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 [triangle]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 [triangle]); 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: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809009970/cv2528sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009970/cv2528Isup2.hkl

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

Acknowledgments

This project was sponsored by the K. C. Wong Magna Fund of Ningbo University and supported by the Expert Project for Key Basic Research of the Ministry of Science and Technology of China (grant No. 2003CCA00800), the Zhejiang Provincial Natural Science Foundation (grant No. Z203067) and the Ningbo Municipal Natural Science Foundation (grant No. 2006 A610061).

supplementary crystallographic information

Comment

A search of the Cambridge Structural Database (Version 5.30, February 2009) showed that most of literature dealing with butane-1,2,3,4-tetracarboxylic acid mainly concentrated in the metal organic coordination polymers (Delgado et al., 2007; Liu et al., 2008). In this paper, we report the crystal structure of butane–1,2,3,4–tetracarboxylic acid dihydrate (Fig. 1).

The asymmetric unit of the title compound contains a half of the butane-1,2,3,4-tetracarboxylic acid molecule and one water molecule. The carboxylic acid group with C1 and C4 atoms are gauche with the C1—C2—C3—C4 torsion angle being 62.13 (1)°, which match well with that in the reported structures (McKee et al., 2007; Najafpour et al., 2008). Intermolecular O—H···O hydrogen bonds (Table 1) form an extensive three-dimensional hydrogen-bonding network, which consolidate the crystal packing.

Experimental

Zn(NO3)2.6H2O (0.1461 g, 1.0 mmol) was added to a stirred aqueous solution of butane-1,2,3,4-tetracarboxylic acid (0.1176 g, 0.50 mmol) in 15 ml H2O, the resulting mixture was stirred for 20 min and then was filtered out. Colorless crystals were obtained from the filtrate (pH=2.80) after standing at room temperature for three months.

Refinement

H atoms bonded to C atoms were palced in geometrically calculated position and were refined using a riding model, with Uiso(H) = 1.2 Ueq(C). H atoms attached to O atoms were found in a difference Fourier synthesis and were refined using a riding model, with the O—H distances fixed as initially found and with Uiso(H) values set at 1.5 Ueq(O).

Figures

Fig. 1.
View of the title compound showing the atomic numbering and 45% probability dispalcement ellipsoids [symmetry code: (i) -x + 1, -y + 1, -z]. H atoms omitted for clarity.

Crystal data

C8H10O8·2H2OF(000) = 284
Mr = 270.19Dx = 1.545 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5478 reflections
a = 7.4668 (15) Åθ = 3.3–27.4°
b = 9.3385 (19) ŵ = 0.15 mm1
c = 8.8406 (18) ÅT = 293 K
β = 109.60 (3)°Platelet, colorless
V = 580.7 (2) Å30.55 × 0.46 × 0.26 mm
Z = 2

Data collection

Rigaku R-AXIS RAPID diffractometer1327 independent reflections
Radiation source: fine-focus sealed tube960 reflections with I > 2σ(I)
graphiteRint = 0.027
Detector resolution: 0 pixels mm-1θmax = 27.4°, θmin = 3.3°
ω scansh = −9→9
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)k = −12→12
Tmin = 0.921, Tmax = 0.965l = −11→11
5478 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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 1.17w = 1/[σ2(Fo2) + (0.0345P)2 + 0.3695P] where P = (Fo2 + 2Fc2)/3
1327 reflections(Δ/σ)max < 0.001
82 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = −0.23 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
O10.1296 (3)0.38628 (19)0.1509 (2)0.0561 (5)
O20.0636 (2)0.20225 (18)−0.0167 (2)0.0494 (5)
H2C−0.01320.18080.03270.074*
C10.1546 (3)0.3207 (2)0.0422 (2)0.0319 (5)
C20.2916 (3)0.3636 (2)−0.0416 (2)0.0371 (5)
H2A0.22010.3991−0.14790.044*
H2B0.36130.2795−0.05470.044*
C30.4336 (3)0.4784 (2)0.0479 (2)0.0294 (4)
H3A0.36400.56300.06330.035*
C40.5554 (3)0.4210 (2)0.2107 (2)0.0299 (4)
O30.6322 (3)0.30568 (17)0.23027 (19)0.0510 (5)
O40.5724 (2)0.50976 (17)0.33017 (16)0.0454 (4)
H4A0.64700.47370.41860.068*
O50.8064 (2)0.09678 (15)0.10900 (16)0.0369 (4)
H5A0.76390.16160.15180.055*
H5B0.83210.03090.17250.055*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0693 (12)0.0600 (11)0.0536 (10)−0.0267 (9)0.0398 (9)−0.0219 (8)
O20.0483 (9)0.0517 (10)0.0578 (10)−0.0243 (8)0.0303 (8)−0.0182 (8)
C10.0289 (10)0.0377 (11)0.0272 (9)−0.0048 (8)0.0069 (8)0.0003 (8)
C20.0337 (10)0.0477 (13)0.0309 (10)−0.0117 (9)0.0124 (8)−0.0073 (9)
C30.0267 (9)0.0347 (11)0.0286 (9)−0.0025 (8)0.0116 (8)−0.0012 (8)
C40.0275 (9)0.0348 (11)0.0294 (9)−0.0040 (8)0.0122 (8)−0.0023 (8)
O30.0669 (11)0.0366 (9)0.0451 (9)0.0151 (8)0.0126 (8)−0.0019 (7)
O40.0549 (10)0.0470 (9)0.0278 (7)0.0170 (7)0.0054 (7)−0.0057 (6)
O50.0434 (8)0.0352 (8)0.0358 (7)−0.0005 (6)0.0182 (6)0.0018 (6)

Geometric parameters (Å, °)

O1—C11.206 (2)C3—C3i1.559 (3)
O2—C11.311 (2)C3—H3A0.9800
O2—H2C0.8523C4—O31.205 (2)
C1—C21.505 (3)C4—O41.315 (2)
C2—C31.528 (3)O4—H4A0.8618
C2—H2A0.9700O5—H5A0.8314
C2—H2B0.9700O5—H5B0.8111
C3—C41.518 (3)
C1—O2—H2C110.1C4—C3—C3i108.55 (18)
O1—C1—O2123.13 (18)C2—C3—C3i110.94 (19)
O1—C1—C2124.71 (18)C4—C3—H3A109.3
O2—C1—C2112.15 (17)C2—C3—H3A109.3
C1—C2—C3113.57 (16)C3i—C3—H3A109.3
C1—C2—H2A108.9O3—C4—O4122.30 (18)
C3—C2—H2A108.9O3—C4—C3123.80 (18)
C1—C2—H2B108.9O4—C4—C3113.89 (17)
C3—C2—H2B108.9C4—O4—H4A110.0
H2A—C2—H2B107.7H5A—O5—H5B105.9
C4—C3—C2109.54 (16)

Symmetry codes: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2C···O5ii0.851.872.707 (2)167
O4—H4A···O5iii0.861.832.689 (2)178
O5—H5A···O30.831.932.754 (2)172
O5—H5B···O1iv0.812.012.814 (2)170

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2528).

References

  • Delgado, L. C., Fabelo, O., Pasàn, J., Delgado, F. S., Lloret, F., Julve, M. & Ruiz-Pérez, C. (2007). Inorg. Chem.46, 7458–7465. [PubMed]
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Liu, Y. Y., Ma, J. F., Yang, J., Ma, J. C. & Su, Z. M. (2008). CrystEngComm, 10, 894–904.
  • McKee, V. & Najafpour, M. M. (2007). Acta Cryst. E63, o741–o743.
  • Najafpour, M. M., Hołyńska, M. & Lis, T. (2008). Acta Cryst. E64, o985. [PMC free article] [PubMed]
  • Rigaku (1998). RAPID-AUTO Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2004). CrystalStructure Rigaku/MSC Inc., The Woodlands, Texas, USA.
  • 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