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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1293.
Published online 2009 May 14. doi:  10.1107/S1600536809016110
PMCID: PMC2969648

cis-Cyclo­hexane-1,4-dicarboxylic acid

Abstract

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 [1An external file that holds a picture, illustration, etc.
Object name is e-65-o1293-efi1.jpg An external file that holds a picture, illustration, etc.
Object name is e-65-o1293-efi1.jpg].

Related literature

For related structures, see: Bi et al. (2003 [triangle], 2004 [triangle]); Chen et al. (2006 [triangle]); Du et al. (2006 [triangle]); Dunitz & Strickler (1966 [triangle]); Kurmoo et al. (2003 [triangle], 2006 [triangle]); Luger et al. (1972 [triangle]).

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Object name is e-65-o1293-scheme1.jpg

Experimental

Crystal data

  • C8H12O4
  • M r = 172.18
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1293-efi3.jpg
  • a = 5.2912 (6) Å
  • b = 6.2611 (6) Å
  • c = 13.1851 (18) Å
  • α = 82.505 (10)°
  • β = 80.309 (11)°
  • γ = 81.875 (10)°
  • V = 423.70 (9) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 296 K
  • 0.24 × 0.20 × 0.10 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.979, T max = 0.989
  • 9807 measured reflections
  • 1925 independent reflections
  • 1222 reflections with I > 2σ(I)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 0.129
  • S = 1.05
  • 1925 reflections
  • 118 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2007 [triangle]); cell refinement: SAINT-Plus (Bruker, 2007 [triangle]); data reduction: SAINT-Plus; 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/S1600536809016110/is2399sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016110/is2399Isup2.hkl

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

Acknowledgments

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).

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

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).

Figures

Fig. 1.
Molecular structure showing 50% probability displacement ellipsoids.
Fig. 2.
Packing diagram viewed down the b axis, The H-bonds are shown as dotted lines.

Crystal data

C8H12O4Z = 2
Mr = 172.18F(000) = 184
Triclinic, P1Dx = 1.350 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.2912 (6) ÅCell parameters from 3560 reflections
b = 6.2611 (6) Åθ = 2.6–26.9°
c = 13.1851 (18) ŵ = 0.11 mm1
α = 82.505 (10)°T = 296 K
β = 80.309 (11)°Plate, colorless
γ = 81.875 (10)°0.24 × 0.20 × 0.10 mm
V = 423.70 (9) Å3

Data collection

Bruker SMART CCD area-detector diffractometer1925 independent reflections
Radiation source: fine-focus sealed tube1222 reflections with I > 2σ(I)
graphiteRint = 0.038
[var phi] and ω scansθmax = 27.5°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −6→6
Tmin = 0.979, Tmax = 0.989k = −7→8
9807 measured reflectionsl = −17→17

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.129w = 1/[σ2(Fo2) + (0.038P)2 + 0.2496P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
1925 reflectionsΔρmax = 0.27 e Å3
118 parametersΔρmin = −0.19 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.057 (12)

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
O10.4359 (3)0.5154 (3)0.88398 (12)0.0583 (5)
O20.2703 (4)0.2964 (3)1.01503 (13)0.0620 (5)
O30.7370 (4)−0.1284 (3)0.57741 (15)0.0709 (6)
O40.8260 (3)0.2120 (3)0.55122 (14)0.0632 (5)
C10.2929 (4)0.3798 (3)0.91784 (16)0.0386 (5)
C20.1278 (4)0.2898 (4)0.85544 (16)0.0420 (5)
H2−0.04880.30210.89320.050*
C30.2176 (4)0.0476 (3)0.84796 (17)0.0457 (6)
H3A0.2410−0.02400.91610.055*
H3B0.0853−0.01740.82420.055*
C40.1185 (4)0.4153 (4)0.74843 (17)0.0493 (6)
H4A−0.02640.37820.72080.059*
H4B0.08780.56940.75570.059*
C50.4695 (4)0.0121 (3)0.77409 (16)0.0411 (5)
H5A0.5175−0.14200.76940.049*
H5B0.60560.06640.80060.049*
C60.3638 (4)0.3713 (4)0.67093 (17)0.0457 (6)
H6A0.33500.43960.60280.055*
H6B0.50290.43460.69070.055*
C70.4420 (4)0.1286 (3)0.66664 (16)0.0411 (5)
H70.30280.07100.64230.049*
C80.6862 (4)0.0769 (4)0.59270 (16)0.0432 (5)
H10.369 (7)0.355 (6)1.048 (3)0.106 (12)*
H80.898 (8)−0.163 (6)0.526 (3)0.128 (13)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0785 (12)0.0610 (11)0.0431 (9)−0.0335 (10)−0.0145 (8)−0.0002 (8)
O20.0795 (13)0.0717 (12)0.0413 (10)−0.0360 (10)−0.0111 (9)0.0020 (8)
O30.0759 (13)0.0525 (11)0.0741 (13)−0.0054 (9)0.0251 (10)−0.0191 (9)
O40.0571 (11)0.0595 (11)0.0685 (12)−0.0124 (9)0.0167 (9)−0.0190 (9)
C10.0371 (11)0.0377 (11)0.0396 (12)−0.0004 (9)−0.0016 (9)−0.0091 (9)
C20.0299 (10)0.0512 (13)0.0452 (12)−0.0048 (9)0.0017 (9)−0.0163 (10)
C30.0454 (12)0.0447 (13)0.0476 (13)−0.0145 (10)0.0045 (10)−0.0131 (10)
C40.0422 (12)0.0544 (14)0.0531 (14)0.0066 (10)−0.0150 (10)−0.0168 (11)
C50.0437 (12)0.0358 (11)0.0422 (12)−0.0034 (9)0.0003 (9)−0.0084 (9)
C60.0490 (13)0.0490 (13)0.0378 (12)0.0017 (10)−0.0098 (10)−0.0038 (10)
C70.0377 (11)0.0491 (13)0.0383 (11)−0.0058 (9)−0.0051 (9)−0.0122 (9)
C80.0450 (12)0.0483 (14)0.0366 (11)−0.0024 (10)−0.0057 (9)−0.0097 (10)

Geometric parameters (Å, °)

O1—C11.209 (2)C3—H3B0.9700
O2—C11.312 (3)C4—C61.527 (3)
O2—H10.88 (4)C4—H4A0.9700
O3—C81.310 (3)C4—H4B0.9700
O3—H81.01 (4)C5—C71.526 (3)
O4—C81.217 (3)C5—H5A0.9700
C1—C21.503 (3)C5—H5B0.9700
C2—C41.528 (3)C6—C71.523 (3)
C2—C31.534 (3)C6—H6A0.9700
C2—H20.9800C6—H6B0.9700
C3—C51.520 (3)C7—C81.505 (3)
C3—H3A0.9700C7—H70.9800
C1—O2—H1110 (2)H4A—C4—H4B107.6
C8—O3—H8114 (2)C3—C5—C7110.71 (18)
O1—C1—O2121.6 (2)C3—C5—H5A109.5
O1—C1—C2124.7 (2)C7—C5—H5A109.5
O2—C1—C2113.66 (19)C3—C5—H5B109.5
C1—C2—C4113.11 (18)C7—C5—H5B109.5
C1—C2—C3109.99 (18)H5A—C5—H5B108.1
C4—C2—C3111.41 (17)C7—C6—C4111.18 (19)
C1—C2—H2107.3C7—C6—H6A109.4
C4—C2—H2107.3C4—C6—H6A109.4
C3—C2—H2107.3C7—C6—H6B109.4
C5—C3—C2111.67 (17)C4—C6—H6B109.4
C5—C3—H3A109.3H6A—C6—H6B108.0
C2—C3—H3A109.3C8—C7—C6113.13 (18)
C5—C3—H3B109.3C8—C7—C5109.85 (18)
C2—C3—H3B109.3C6—C7—C5111.08 (17)
H3A—C3—H3B107.9C8—C7—H7107.5
C6—C4—C2114.13 (18)C6—C7—H7107.5
C6—C4—H4A108.7C5—C7—H7107.5
C2—C4—H4A108.7O4—C8—O3122.7 (2)
C6—C4—H4B108.7O4—C8—C7123.5 (2)
C2—C4—H4B108.7O3—C8—C7113.8 (2)
O1—C1—C2—C4−10.6 (3)C2—C4—C6—C751.0 (2)
O2—C1—C2—C4169.74 (18)C4—C6—C7—C8−178.86 (18)
O1—C1—C2—C3114.7 (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—C658.6 (2)
C4—C2—C3—C552.3 (2)C6—C7—C8—O49.4 (3)
C1—C2—C4—C674.9 (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—O364.1 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H1···O1i0.88 (4)1.81 (4)2.684 (2)178 (4)
O3—H8···O4ii1.01 (4)1.65 (4)2.658 (2)175 (4)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2399).

References

  • Bi, W., Cao, R., Sun, D., Yuan, D., Li, X. & Hong, M. (2003). Inorg. Chem. Commun.6, 1426–1428.
  • Bi, W., Cao, R., Sun, D., Yuan, D., Li, X., Wang, Y., Li, X. & Hong, M. (2004). Chem. Commun. pp. 2104–2105. [PubMed]
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  • Chen, B., Fronczek, F. R., Courtney, B. H. & Zapata, F. (2006). Cryst. Growth Des.6, 825–828.
  • Du, M., Zhang, Z. & Zhao, X. (2006). Cryst. Growth Des.6, 390–396.
  • Dunitz, J. D. & Strickler, P. (1966). Helv. Chim. Acta, 49, 2505–2515.
  • Kurmoo, M., Kumagai, H., Akita-Tanaka, M., Inoue, K. & Takagi, S. (2006). Inorg. Chem.45, 1627–1637. [PubMed]
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