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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1719.
Published online 2008 August 6. doi:  10.1107/S160053680802504X
PMCID: PMC2960595

Benzene-1,3-diacetic acid

Abstract

Mol­ecules of the title compound, C10H10O4, are connected through O—H(...)O hydrogen-bonding inter­actions into chains running along the c axis.

Related literature

For related literature, see Huo et al. (2004 [triangle]); Ma et al. (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1719-scheme1.jpg

Experimental

Crystal data

  • C10H10O4
  • M r = 194.18
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1719-efi1.jpg
  • a = 4.9506 (9) Å
  • b = 10.0840 (17) Å
  • c = 18.576 (3) Å
  • V = 927.3 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 293 (2) K
  • 0.31 × 0.21 × 0.19 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1998 [triangle])T min = 0.965, T max = 0.981
  • 5569 measured reflections
  • 1094 independent reflections
  • 970 reflections with I > 2σ(I)
  • R int = 0.020

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.121
  • S = 1.06
  • 1094 reflections
  • 127 parameters
  • H-atom parameters constrained
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.12 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SMART; data reduction: SAINT (Bruker, 1998 [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: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802504X/bt2762sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802504X/bt2762Isup2.hkl

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

Acknowledgments

The author thanks the Beihua University for supporting this work.

supplementary crystallographic information

Comment

The self-organization of small molecules with O—H···O and other weak intermolecular interactions is used to create one-, two-, and three-dimensional networks in crystalline solids (Huo et al., 2004). Recently, aromatic di- or poly(carboxylic acids) have been investigated in the area of solid state and material science (Ma et al., 2003). The title compound was synthesized from benzene-1,3-diacetic acid. In the crystal, molecules of the title compound are connected through O—H···O H-bonding interactions to chains running along the c-axis.

Experimental

A hot aqueous solution of benzene-1,3-diacetic acid (1 mmol) was stirred until the white solids were dissolved. The clear solution was allowed to cool to room temperature and evaporated in air for 5 days. Then, colourless crystals of the title compound were obtained.

Refinement

In the absence of anomalous scatterers Friedel pairs (714) were merged. H atoms were generated geometrically and refined as riding atoms with O—H= 0.82Å, Caromatic—H= 0.93Å Cmethylene—H= 0.97Å and Uiso(H)= 1.2 times Ueq(C) or Uiso(H)= 1.5 times Ueq(O).

Figures

Fig. 1.
The structure of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C10H10O4F000 = 408
Mr = 194.18Dx = 1.391 Mg m3
Orthorhombic, P212121Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1094 reflections
a = 4.9506 (9) Åθ = 1.1–26.1º
b = 10.0840 (17) ŵ = 0.11 mm1
c = 18.576 (3) ÅT = 293 (2) K
V = 927.3 (3) Å3Block, colorless
Z = 40.31 × 0.21 × 0.19 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer1094 independent reflections
Radiation source: fine-focus sealed tube970 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.020
T = 293(2) Kθmax = 26.1º
[var phi] and ω scansθmin = 2.2º
Absorption correction: multi-scan(SAINT; Bruker, 1998)h = −6→5
Tmin = 0.965, Tmax = 0.981k = −10→12
5569 measured reflectionsl = −22→22

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.121  w = 1/[σ2(Fo2) + (0.0719P)2 + 0.1185P] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
1094 reflectionsΔρmax = 0.21 e Å3
127 parametersΔρmin = −0.12 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
O10.6445 (5)1.3039 (2)0.89747 (14)0.0773 (7)
O40.4524 (5)0.53787 (19)0.85467 (15)0.0880 (8)
H4A0.53180.46770.86160.132*
O21.0157 (5)1.3432 (2)0.83572 (13)0.0805 (7)
H20.93201.41130.82650.121*
O30.8315 (5)0.5825 (3)0.79804 (15)0.0910 (8)
C80.7293 (5)0.9447 (2)0.85307 (14)0.0504 (6)
H80.81980.95420.80950.060*
C10.8739 (6)1.2698 (2)0.87529 (15)0.0524 (7)
C70.5408 (5)0.8441 (2)0.86027 (14)0.0503 (6)
C30.7872 (6)1.0315 (2)0.90849 (15)0.0542 (7)
C20.9924 (6)1.1399 (3)0.89799 (18)0.0668 (8)
H2A1.09001.15260.94270.080*
H2B1.12161.11160.86190.080*
C100.5972 (6)0.6126 (3)0.81796 (15)0.0557 (7)
C90.4895 (7)0.7476 (3)0.79898 (15)0.0626 (8)
H9A0.29710.74180.78970.075*
H9B0.57710.77940.75560.075*
C60.4047 (6)0.8332 (3)0.92448 (16)0.0642 (8)
H60.27430.76760.93000.077*
C50.4588 (7)0.9185 (3)0.98098 (17)0.0751 (10)
H50.36600.90981.02420.090*
C40.6514 (7)1.0169 (3)0.97298 (15)0.0669 (8)
H40.68951.07351.01120.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0676 (14)0.0528 (11)0.1114 (17)0.0114 (11)0.0163 (14)0.0152 (11)
O40.0761 (15)0.0466 (10)0.141 (2)0.0002 (11)0.0161 (15)0.0274 (13)
O20.0756 (14)0.0531 (11)0.1130 (17)0.0032 (12)0.0200 (13)0.0085 (12)
O30.0769 (16)0.0728 (15)0.123 (2)0.0130 (14)0.0221 (15)0.0279 (14)
C80.0480 (13)0.0394 (12)0.0637 (15)0.0030 (11)0.0000 (12)0.0093 (11)
C10.0520 (14)0.0367 (12)0.0684 (16)−0.0057 (12)−0.0130 (14)−0.0069 (12)
C70.0445 (13)0.0378 (12)0.0686 (16)0.0017 (10)−0.0042 (13)0.0142 (11)
C30.0507 (15)0.0343 (11)0.0775 (17)0.0080 (11)−0.0106 (13)0.0041 (12)
C20.0531 (16)0.0452 (14)0.102 (2)−0.0005 (13)−0.0150 (17)−0.0032 (15)
C100.0578 (16)0.0420 (13)0.0674 (16)−0.0084 (13)−0.0140 (14)0.0039 (12)
C90.0645 (17)0.0489 (15)0.0745 (17)−0.0043 (14)−0.0209 (16)0.0103 (13)
C60.0559 (17)0.0465 (14)0.090 (2)0.0036 (14)0.0103 (16)0.0181 (14)
C50.090 (2)0.0599 (18)0.0756 (19)0.0226 (19)0.0233 (18)0.0163 (15)
C40.083 (2)0.0498 (15)0.0682 (17)0.0193 (17)−0.0042 (16)−0.0023 (14)

Geometric parameters (Å, °)

O1—C11.256 (4)C3—C41.382 (4)
O4—C101.244 (4)C3—C21.505 (4)
O4—H4A0.8200C2—H2A0.9700
O2—C11.258 (3)C2—H2B0.9700
O2—H20.8200C10—C91.503 (4)
O3—C101.255 (4)C9—H9A0.9700
C8—C31.381 (3)C9—H9B0.9700
C8—C71.385 (3)C6—C51.383 (4)
C8—H80.9300C6—H60.9300
C1—C21.496 (4)C5—C41.384 (5)
C7—C61.375 (4)C5—H50.9300
C7—C91.519 (4)C4—H40.9300
C10—O4—H4A109.5H2A—C2—H2B107.6
C1—O2—H2109.5O4—C10—O3123.2 (3)
C3—C8—C7122.1 (2)O4—C10—C9118.2 (3)
C3—C8—H8118.9O3—C10—C9118.6 (3)
C7—C8—H8118.9C10—C9—C7110.2 (2)
O1—C1—O2122.3 (3)C10—C9—H9A109.6
O1—C1—C2120.2 (3)C7—C9—H9A109.6
O2—C1—C2117.5 (3)C10—C9—H9B109.6
C6—C7—C8118.2 (3)C7—C9—H9B109.6
C6—C7—C9121.1 (3)H9A—C9—H9B108.1
C8—C7—C9120.6 (2)C7—C6—C5120.9 (3)
C8—C3—C4118.5 (3)C7—C6—H6119.5
C8—C3—C2120.2 (3)C5—C6—H6119.5
C4—C3—C2121.2 (3)C6—C5—C4119.9 (3)
C1—C2—C3114.1 (2)C6—C5—H5120.1
C1—C2—H2A108.7C4—C5—H5120.1
C3—C2—H2A108.7C3—C4—C5120.3 (3)
C1—C2—H2B108.7C3—C4—H4119.8
C3—C2—H2B108.7C5—C4—H4119.8

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O4—H4A···O1i0.821.872.665 (3)165
O2—H2···O3ii0.821.872.673 (3)165

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2762).

References

  • Bruker (1998). SMARTSAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Huo, L.-H., Gao, S., Zhao, H., Zain, S. M. & Ng, S. W. (2004). Acta Cryst. E60, o1394–o1396.
  • Ma, J.-F., Yang, J., Zheng, G.-L., Li, L. & Liu, J.-F. (2003). Inorg. Chem.42, 7531–7534. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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