Acta Cryst. (2009). E65, o1293 [ doi:10.1107/S1600536809016110 ]
In the title compound, C8H12O4, the two carboxyl groups are on the same side of the cyclohexane ring and the ring adopts a chair conformation. Adjacent molecules related by an inversion centre are linked by pairs of O-H
O hydrogen bonds, forming a zigzag chain along [1
].
C8H12O4 (1 mmol, 172 mg; mixture of trans- and cis-ACROS) was disloved into 50 ml of CD3OD. The solution was stirring and refluxing for 12 h, and the clear solution was allowed to evaporate slowly in the inert atmosphere. Nice plate crystals of the title compound were obtained after 5 days. The crystals were filtered, washed by cool EtOH and dried in the air.
H atoms on O atoms were located in a difference Fourier map and were refined freely. Other H atoms were refined as riding, with C—H = 0.97 or 0.98 Å, and with Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); 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]](./is2399fig1thm.gif)
| Fig. 1. Molecular structure showing 50% probability displacement ellipsoids. |
![[Figure 2]](./is2399fig2thm.gif)
| Fig. 2. Packing diagram viewed down the b axis, The H-bonds are shown as dotted lines. |
| C8H12O4 | Z = 2 |
| Mr = 172.18 | F000 = 184 |
| Triclinic, P1 | Dx = 1.350 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation λ = 0.71073 Å |
| a = 5.2912 (6) Å | Cell parameters from 3560 reflections |
| b = 6.2611 (6) Å | θ = 2.6–26.9º |
| c = 13.1851 (18) Å | µ = 0.11 mm−1 |
| α = 82.505 (10)º | T = 296 K |
| β = 80.309 (11)º | Plate, colorless |
| γ = 81.875 (10)º | 0.24 × 0.20 × 0.10 mm |
| V = 423.70 (9) Å3 |
| Bruker SMART CCD area-detector diffractometer | 1925 independent reflections |
| Radiation source: fine-focus sealed tube | 1222 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.038 |
| T = 296 K | θmax = 27.5º |
| φ and ω scans | θmin = 3.5º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −6→6 |
| Tmin = 0.979, Tmax = 0.989 | k = −7→8 |
| 9807 measured reflections | l = −17→17 |
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
| R[F2 > 2σ(F2)] = 0.055 | w = 1/[σ2(Fo2) + (0.038P)2 + 0.2496P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.129 | (Δ/σ)max < 0.001 |
| S = 1.05 | Δρmax = 0.27 e Å−3 |
| 1925 reflections | Δρmin = −0.19 e Å−3 |
| 118 parameters | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.057 (12) |
| Secondary atom site location: difference Fourier map |
| C8H12O4 | γ = 81.875 (10)º |
| Mr = 172.18 | V = 423.70 (9) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 5.2912 (6) Å | Mo Kα |
| b = 6.2611 (6) Å | µ = 0.11 mm−1 |
| c = 13.1851 (18) Å | T = 296 K |
| α = 82.505 (10)º | 0.24 × 0.20 × 0.10 mm |
| β = 80.309 (11)º |
| Bruker SMART CCD area-detector diffractometer | 1925 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1222 reflections with I > 2σ(I) |
| Tmin = 0.979, Tmax = 0.989 | Rint = 0.038 |
| 9807 measured reflections |
| R[F2 > 2σ(F2)] = 0.055 | 118 parameters |
| wR(F2) = 0.129 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.05 | Δρmax = 0.27 e Å−3 |
| 1925 reflections | Δρmin = −0.19 e Å−3 |
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 | 0.4359 (3) | 0.5154 (3) | 0.88398 (12) | 0.0583 (5) | |
| O2 | 0.2703 (4) | 0.2964 (3) | 1.01503 (13) | 0.0620 (5) | |
| O3 | 0.7370 (4) | −0.1284 (3) | 0.57741 (15) | 0.0709 (6) | |
| O4 | 0.8260 (3) | 0.2120 (3) | 0.55122 (14) | 0.0632 (5) | |
| C1 | 0.2929 (4) | 0.3798 (3) | 0.91784 (16) | 0.0386 (5) | |
| C2 | 0.1278 (4) | 0.2898 (4) | 0.85544 (16) | 0.0420 (5) | |
| H2 | −0.0488 | 0.3021 | 0.8932 | 0.050* | |
| C3 | 0.2176 (4) | 0.0476 (3) | 0.84796 (17) | 0.0457 (6) | |
| H3A | 0.2410 | −0.0240 | 0.9161 | 0.055* | |
| H3B | 0.0853 | −0.0174 | 0.8242 | 0.055* | |
| C4 | 0.1185 (4) | 0.4153 (4) | 0.74843 (17) | 0.0493 (6) | |
| H4A | −0.0264 | 0.3782 | 0.7208 | 0.059* | |
| H4B | 0.0878 | 0.5694 | 0.7557 | 0.059* | |
| C5 | 0.4695 (4) | 0.0121 (3) | 0.77409 (16) | 0.0411 (5) | |
| H5A | 0.5175 | −0.1420 | 0.7694 | 0.049* | |
| H5B | 0.6056 | 0.0664 | 0.8006 | 0.049* | |
| C6 | 0.3638 (4) | 0.3713 (4) | 0.67093 (17) | 0.0457 (6) | |
| H6A | 0.3350 | 0.4396 | 0.6028 | 0.055* | |
| H6B | 0.5029 | 0.4346 | 0.6907 | 0.055* | |
| C7 | 0.4420 (4) | 0.1286 (3) | 0.66664 (16) | 0.0411 (5) | |
| H7 | 0.3028 | 0.0710 | 0.6423 | 0.049* | |
| C8 | 0.6862 (4) | 0.0769 (4) | 0.59270 (16) | 0.0432 (5) | |
| H1 | 0.369 (7) | 0.355 (6) | 1.048 (3) | 0.106 (12)* | |
| H8 | 0.898 (8) | −0.163 (6) | 0.526 (3) | 0.128 (13)* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0785 (12) | 0.0610 (11) | 0.0431 (9) | −0.0335 (10) | −0.0145 (8) | −0.0002 (8) |
| O2 | 0.0795 (13) | 0.0717 (12) | 0.0413 (10) | −0.0360 (10) | −0.0111 (9) | 0.0020 (8) |
| O3 | 0.0759 (13) | 0.0525 (11) | 0.0741 (13) | −0.0054 (9) | 0.0251 (10) | −0.0191 (9) |
| O4 | 0.0571 (11) | 0.0595 (11) | 0.0685 (12) | −0.0124 (9) | 0.0167 (9) | −0.0190 (9) |
| C1 | 0.0371 (11) | 0.0377 (11) | 0.0396 (12) | −0.0004 (9) | −0.0016 (9) | −0.0091 (9) |
| C2 | 0.0299 (10) | 0.0512 (13) | 0.0452 (12) | −0.0048 (9) | 0.0017 (9) | −0.0163 (10) |
| C3 | 0.0454 (12) | 0.0447 (13) | 0.0476 (13) | −0.0145 (10) | 0.0045 (10) | −0.0131 (10) |
| C4 | 0.0422 (12) | 0.0544 (14) | 0.0531 (14) | 0.0066 (10) | −0.0150 (10) | −0.0168 (11) |
| C5 | 0.0437 (12) | 0.0358 (11) | 0.0422 (12) | −0.0034 (9) | 0.0003 (9) | −0.0084 (9) |
| C6 | 0.0490 (13) | 0.0490 (13) | 0.0378 (12) | 0.0017 (10) | −0.0098 (10) | −0.0038 (10) |
| C7 | 0.0377 (11) | 0.0491 (13) | 0.0383 (11) | −0.0058 (9) | −0.0051 (9) | −0.0122 (9) |
| C8 | 0.0450 (12) | 0.0483 (14) | 0.0366 (11) | −0.0024 (10) | −0.0057 (9) | −0.0097 (10) |
| O1—C1 | 1.209 (2) | C3—H3B | 0.9700 |
| O2—C1 | 1.312 (3) | C4—C6 | 1.527 (3) |
| O2—H1 | 0.88 (4) | C4—H4A | 0.9700 |
| O3—C8 | 1.310 (3) | C4—H4B | 0.9700 |
| O3—H8 | 1.01 (4) | C5—C7 | 1.526 (3) |
| O4—C8 | 1.217 (3) | C5—H5A | 0.9700 |
| C1—C2 | 1.503 (3) | C5—H5B | 0.9700 |
| C2—C4 | 1.528 (3) | C6—C7 | 1.523 (3) |
| C2—C3 | 1.534 (3) | C6—H6A | 0.9700 |
| C2—H2 | 0.9800 | C6—H6B | 0.9700 |
| C3—C5 | 1.520 (3) | C7—C8 | 1.505 (3) |
| C3—H3A | 0.9700 | C7—H7 | 0.9800 |
| C1—O2—H1 | 110 (2) | H4A—C4—H4B | 107.6 |
| C8—O3—H8 | 114 (2) | C3—C5—C7 | 110.71 (18) |
| O1—C1—O2 | 121.6 (2) | C3—C5—H5A | 109.5 |
| O1—C1—C2 | 124.7 (2) | C7—C5—H5A | 109.5 |
| O2—C1—C2 | 113.66 (19) | C3—C5—H5B | 109.5 |
| C1—C2—C4 | 113.11 (18) | C7—C5—H5B | 109.5 |
| C1—C2—C3 | 109.99 (18) | H5A—C5—H5B | 108.1 |
| C4—C2—C3 | 111.41 (17) | C7—C6—C4 | 111.18 (19) |
| C1—C2—H2 | 107.3 | C7—C6—H6A | 109.4 |
| C4—C2—H2 | 107.3 | C4—C6—H6A | 109.4 |
| C3—C2—H2 | 107.3 | C7—C6—H6B | 109.4 |
| C5—C3—C2 | 111.67 (17) | C4—C6—H6B | 109.4 |
| C5—C3—H3A | 109.3 | H6A—C6—H6B | 108.0 |
| C2—C3—H3A | 109.3 | C8—C7—C6 | 113.13 (18) |
| C5—C3—H3B | 109.3 | C8—C7—C5 | 109.85 (18) |
| C2—C3—H3B | 109.3 | C6—C7—C5 | 111.08 (17) |
| H3A—C3—H3B | 107.9 | C8—C7—H7 | 107.5 |
| C6—C4—C2 | 114.13 (18) | C6—C7—H7 | 107.5 |
| C6—C4—H4A | 108.7 | C5—C7—H7 | 107.5 |
| C2—C4—H4A | 108.7 | O4—C8—O3 | 122.7 (2) |
| C6—C4—H4B | 108.7 | O4—C8—C7 | 123.5 (2) |
| C2—C4—H4B | 108.7 | O3—C8—C7 | 113.8 (2) |
| O1—C1—C2—C4 | −10.6 (3) | C2—C4—C6—C7 | 51.0 (2) |
| O2—C1—C2—C4 | 169.74 (18) | C4—C6—C7—C8 | −178.86 (18) |
| O1—C1—C2—C3 | 114.7 (2) | C4—C6—C7—C5 | −54.8 (2) |
| O2—C1—C2—C3 | −65.0 (2) | C3—C5—C7—C8 | −175.50 (17) |
| C1—C2—C3—C5 | −74.0 (2) | C3—C5—C7—C6 | 58.6 (2) |
| C4—C2—C3—C5 | 52.3 (2) | C6—C7—C8—O4 | 9.4 (3) |
| C1—C2—C4—C6 | 74.9 (2) | C5—C7—C8—O4 | −115.3 (2) |
| C3—C2—C4—C6 | −49.6 (2) | C6—C7—C8—O3 | −171.16 (19) |
| C2—C3—C5—C7 | −57.3 (2) | C5—C7—C8—O3 | 64.1 (2) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2—H1···O1i | 0.88 (4) | 1.81 (4) | 2.684 (2) | 178 (4) |
| O3—H8···O4ii | 1.01 (4) | 1.65 (4) | 2.658 (2) | 175 (4) |
| Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+2, −y, −z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2—H1···O1i | 0.88 (4) | 1.81 (4) | 2.684 (2) | 178 (4) |
| O3—H8···O4ii | 1.01 (4) | 1.65 (4) | 2.658 (2) | 175 (4) |
| Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+2, −y, −z+1. |
The authors are grateful for funding support from the National Natural Science Foundation of China (20471015; 20874012) and the Foundation for Key Programs of the Ministry of Education, China (DB—O57).
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According to the literatures, there are a few structures incorporating 1,4-cis-Cyclohexane dicarboxylic acid (Bi et al., 2004). Although the structures of its isomer in trans conformation have been described for more than 40 years (Dunitz & Strickler, 1996; Luger et al., 1972), the structure of the title compound, (I), has only been reported as a co-crystal by Du et al. (2006).
According to the results of single X-ray diffraction analysis, there is one complete molecule in the asymmetric unit, and the molecule is in a general position (Fig. 1). The geometry of the molecule is similar to the one observed by Du et al. (2006). The bond lengths are comparable to those in its isomers in trans conformations (Bi et al., 2003; Chen et al., 2006; Kurmoo et al., 2003, 2006).
Strong hydrogen bonds between two adjacent carboxylate groups link molecules into a zigzag chain along the [111] direction. The zigzag chains are packed into three-dimensional motif (Fig. 2).