Acta Cryst. (2008). E64, o1719 [ doi:10.1107/S160053680802504X ]
Molecules of the title compound, C10H10O4, are connected through O-H
O hydrogen-bonding interactions into chains running along the c axis.
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.
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).
Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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).
![[Figure 1]](./bt2762fig1thm.gif)
| Fig. 1. The structure of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. |
| C10H10O4 | F000 = 408 |
| Mr = 194.18 | Dx = 1.391 Mg m−3 |
| Orthorhombic, P212121 | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: P 2ac 2ab | Cell parameters from 1094 reflections |
| a = 4.9506 (9) Å | θ = 1.1–26.1º |
| b = 10.0840 (17) Å | µ = 0.11 mm−1 |
| c = 18.576 (3) Å | T = 293 (2) K |
| V = 927.3 (3) Å3 | Block, colorless |
| Z = 4 | 0.31 × 0.21 × 0.19 mm |
| Bruker SMART APEX CCD area-detector diffractometer | 1094 independent reflections |
| Radiation source: fine-focus sealed tube | 970 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.020 |
| T = 293(2) K | θmax = 26.1º |
| φ and ω scans | θmin = 2.2º |
| Absorption correction: multi-scan (SAINT; Bruker, 1998) | h = −6→5 |
| Tmin = 0.965, Tmax = 0.981 | k = −10→12 |
| 5569 measured reflections | l = −22→22 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.044 | H-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 reflections | Δρmax = 0.21 e Å−3 |
| 127 parameters | Δρmin = −0.12 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| C10H10O4 | V = 927.3 (3) Å3 |
| Mr = 194.18 | Z = 4 |
| Orthorhombic, P212121 | Mo Kα |
| a = 4.9506 (9) Å | µ = 0.11 mm−1 |
| b = 10.0840 (17) Å | T = 293 (2) K |
| c = 18.576 (3) Å | 0.31 × 0.21 × 0.19 mm |
| Bruker SMART APEX CCD area-detector diffractometer | 1094 independent reflections |
| Absorption correction: multi-scan (SAINT; Bruker, 1998) | 970 reflections with I > 2σ(I) |
| Tmin = 0.965, Tmax = 0.981 | Rint = 0.020 |
| 5569 measured reflections |
| R[F2 > 2σ(F2)] = 0.044 | Δρmax = 0.21 e Å−3 |
| wR(F2) = 0.121 | Δρmin = −0.12 e Å−3 |
| S = 1.06 | Absolute structure: ? |
| 1094 reflections | Flack parameter: ? |
| 127 parameters | Rogers parameter: ? |
| H-atom parameters constrained |
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. |
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.6445 (5) | 1.3039 (2) | 0.89747 (14) | 0.0773 (7) | |
| O4 | 0.4524 (5) | 0.53787 (19) | 0.85467 (15) | 0.0880 (8) | |
| H4A | 0.5318 | 0.4677 | 0.8616 | 0.132* | |
| O2 | 1.0157 (5) | 1.3432 (2) | 0.83572 (13) | 0.0805 (7) | |
| H2 | 0.9320 | 1.4113 | 0.8265 | 0.121* | |
| O3 | 0.8315 (5) | 0.5825 (3) | 0.79804 (15) | 0.0910 (8) | |
| C8 | 0.7293 (5) | 0.9447 (2) | 0.85307 (14) | 0.0504 (6) | |
| H8 | 0.8198 | 0.9542 | 0.8095 | 0.060* | |
| C1 | 0.8739 (6) | 1.2698 (2) | 0.87529 (15) | 0.0524 (7) | |
| C7 | 0.5408 (5) | 0.8441 (2) | 0.86027 (14) | 0.0503 (6) | |
| C3 | 0.7872 (6) | 1.0315 (2) | 0.90849 (15) | 0.0542 (7) | |
| C2 | 0.9924 (6) | 1.1399 (3) | 0.89799 (18) | 0.0668 (8) | |
| H2A | 1.0900 | 1.1526 | 0.9427 | 0.080* | |
| H2B | 1.1216 | 1.1116 | 0.8619 | 0.080* | |
| C10 | 0.5972 (6) | 0.6126 (3) | 0.81796 (15) | 0.0557 (7) | |
| C9 | 0.4895 (7) | 0.7476 (3) | 0.79898 (15) | 0.0626 (8) | |
| H9A | 0.2971 | 0.7418 | 0.7897 | 0.075* | |
| H9B | 0.5771 | 0.7794 | 0.7556 | 0.075* | |
| C6 | 0.4047 (6) | 0.8332 (3) | 0.92448 (16) | 0.0642 (8) | |
| H6 | 0.2743 | 0.7676 | 0.9300 | 0.077* | |
| C5 | 0.4588 (7) | 0.9185 (3) | 0.98098 (17) | 0.0751 (10) | |
| H5 | 0.3660 | 0.9098 | 1.0242 | 0.090* | |
| C4 | 0.6514 (7) | 1.0169 (3) | 0.97298 (15) | 0.0669 (8) | |
| H4 | 0.6895 | 1.0735 | 1.0112 | 0.080* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0676 (14) | 0.0528 (11) | 0.1114 (17) | 0.0114 (11) | 0.0163 (14) | 0.0152 (11) |
| O4 | 0.0761 (15) | 0.0466 (10) | 0.141 (2) | 0.0002 (11) | 0.0161 (15) | 0.0274 (13) |
| O2 | 0.0756 (14) | 0.0531 (11) | 0.1130 (17) | 0.0032 (12) | 0.0200 (13) | 0.0085 (12) |
| O3 | 0.0769 (16) | 0.0728 (15) | 0.123 (2) | 0.0130 (14) | 0.0221 (15) | 0.0279 (14) |
| C8 | 0.0480 (13) | 0.0394 (12) | 0.0637 (15) | 0.0030 (11) | 0.0000 (12) | 0.0093 (11) |
| C1 | 0.0520 (14) | 0.0367 (12) | 0.0684 (16) | −0.0057 (12) | −0.0130 (14) | −0.0069 (12) |
| C7 | 0.0445 (13) | 0.0378 (12) | 0.0686 (16) | 0.0017 (10) | −0.0042 (13) | 0.0142 (11) |
| C3 | 0.0507 (15) | 0.0343 (11) | 0.0775 (17) | 0.0080 (11) | −0.0106 (13) | 0.0041 (12) |
| C2 | 0.0531 (16) | 0.0452 (14) | 0.102 (2) | −0.0005 (13) | −0.0150 (17) | −0.0032 (15) |
| C10 | 0.0578 (16) | 0.0420 (13) | 0.0674 (16) | −0.0084 (13) | −0.0140 (14) | 0.0039 (12) |
| C9 | 0.0645 (17) | 0.0489 (15) | 0.0745 (17) | −0.0043 (14) | −0.0209 (16) | 0.0103 (13) |
| C6 | 0.0559 (17) | 0.0465 (14) | 0.090 (2) | 0.0036 (14) | 0.0103 (16) | 0.0181 (14) |
| C5 | 0.090 (2) | 0.0599 (18) | 0.0756 (19) | 0.0226 (19) | 0.0233 (18) | 0.0163 (15) |
| C4 | 0.083 (2) | 0.0498 (15) | 0.0682 (17) | 0.0193 (17) | −0.0042 (16) | −0.0023 (14) |
| O1—C1 | 1.256 (4) | C3—C4 | 1.382 (4) |
| O4—C10 | 1.244 (4) | C3—C2 | 1.505 (4) |
| O4—H4A | 0.8200 | C2—H2A | 0.9700 |
| O2—C1 | 1.258 (3) | C2—H2B | 0.9700 |
| O2—H2 | 0.8200 | C10—C9 | 1.503 (4) |
| O3—C10 | 1.255 (4) | C9—H9A | 0.9700 |
| C8—C3 | 1.381 (3) | C9—H9B | 0.9700 |
| C8—C7 | 1.385 (3) | C6—C5 | 1.383 (4) |
| C8—H8 | 0.9300 | C6—H6 | 0.9300 |
| C1—C2 | 1.496 (4) | C5—C4 | 1.384 (5) |
| C7—C6 | 1.375 (4) | C5—H5 | 0.9300 |
| C7—C9 | 1.519 (4) | C4—H4 | 0.9300 |
| C10—O4—H4A | 109.5 | H2A—C2—H2B | 107.6 |
| C1—O2—H2 | 109.5 | O4—C10—O3 | 123.2 (3) |
| C3—C8—C7 | 122.1 (2) | O4—C10—C9 | 118.2 (3) |
| C3—C8—H8 | 118.9 | O3—C10—C9 | 118.6 (3) |
| C7—C8—H8 | 118.9 | C10—C9—C7 | 110.2 (2) |
| O1—C1—O2 | 122.3 (3) | C10—C9—H9A | 109.6 |
| O1—C1—C2 | 120.2 (3) | C7—C9—H9A | 109.6 |
| O2—C1—C2 | 117.5 (3) | C10—C9—H9B | 109.6 |
| C6—C7—C8 | 118.2 (3) | C7—C9—H9B | 109.6 |
| C6—C7—C9 | 121.1 (3) | H9A—C9—H9B | 108.1 |
| C8—C7—C9 | 120.6 (2) | C7—C6—C5 | 120.9 (3) |
| C8—C3—C4 | 118.5 (3) | C7—C6—H6 | 119.5 |
| C8—C3—C2 | 120.2 (3) | C5—C6—H6 | 119.5 |
| C4—C3—C2 | 121.2 (3) | C6—C5—C4 | 119.9 (3) |
| C1—C2—C3 | 114.1 (2) | C6—C5—H5 | 120.1 |
| C1—C2—H2A | 108.7 | C4—C5—H5 | 120.1 |
| C3—C2—H2A | 108.7 | C3—C4—C5 | 120.3 (3) |
| C1—C2—H2B | 108.7 | C3—C4—H4 | 119.8 |
| C3—C2—H2B | 108.7 | C5—C4—H4 | 119.8 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O4—H4A···O1i | 0.82 | 1.87 | 2.665 (3) | 165 |
| O2—H2···O3ii | 0.82 | 1.87 | 2.673 (3) | 165 |
| Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O4—H4A···O1i | 0.82 | 1.87 | 2.665 (3) | 165 |
| O2—H2···O3ii | 0.82 | 1.87 | 2.673 (3) | 165 |
| Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z. |
Bruker (1998). SMART and SAINT. 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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
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.