organic compounds
trans-Cyclohex-2-ene-1,4-diyl bis(4-nitrophenyl) dicarbonate
aH. E. J. Research Institute of Chemistry, International Center for Chemical Sciences, University of Karachi, Karachi 75270, Pakistan, and bDepartment of Chemistry, University of Toronto, Toronto, Ontario, M5S 3H6, Canada
*Correspondence e-mail: alough@chem.utoronto.ca
Although the title molecule, C20H16N2O10, does not possess molecular inversion symmetry, it lies on a crystallographic inversion centre which imposes disorder on the central cyclohexene ring. In addition, the cyclohexene ring has non-symmetry-related disorder over two sites, with the ratio of the major and minor components being 0.54:0.46. The overall effect is to produce four disorder components for the atoms of the cyclohexene ring. The side chain is perfectly ordered and the dihedral angle between the atoms of the carbonate group (O=CO2—) and the benzene ring is 72.99 (6)°.
Related literature
For related literature, see: Ali et al. (2008); Ericsson & Hult (1991); Fréchet et al. (1986, 1987).
Experimental
Crystal data
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Data collection: COLLECT (Nonius, 2002); cell DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL/PC (Sheldrick, 2001); molecular graphics: PLATON (Spek, 2003) ; software used to prepare material for publication: SHELXTL/PC.
Supporting information
https://doi.org/10.1107/S1600536807065993/hb2674sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807065993/hb2674Isup2.hkl
A solution of 4-nitrophenylchloroformate (1.41 g, 7.0 mmol) in dry dichloromethane (20 ml) was added dropwise via a 100 ml separating funnel into a solution of cyclohex-2-ene-1,4-diol (trans isomer) (0.40 g, 3.5 mmol) in anhydrous pyridine (0.49 g, 0.5 ml, 6.2 mmol) and dry dichloromethane (10 ml) in a 100 ml round-bottom flask. A white suspension appeared which was allowed to stir gently at room temperature for 12 h. After this time more dry dichloromethane (25 ml) was added, which dissolved the suspension and then the reaction mixture was stirred for another 6 h. Then it was quenched by adding deionized water (30 ml). The reaction mixture was transferred to a separating funnel (250 ml), and the lower organic phase was removed. The aqueous phase was washed with dichloromethane (20 ml × 2), and all the dichloromethane solutions were combined. These were then washed with deionized water (20 ml × 2), a 1.0% solution of acetic acid (30 ml × 2) and once more with deionized water (25 ml × 2), and then dried over anhydrous magnesium sulfate and filtered. After filtration, the solvent was removed by rotary evaporation. The product was dried in air overnight in a fume hood and then in a vacuum oven for 24 h at room temperature (< 1 Torr). The desired product was obtained in good yield (1.35 g, 86.5%) as a white crystalline solid. The product was recrystallized in dichloromethane and colourless needles of (I) were obtained by slow evaporation of solvent at room temperature. In addition to the X-ray
the structure of the crystalline sample was confirmed by Mass and NMR (1H and 13C)Spectroscopy.All the hydrogen atoms were placed in calculated positions with C—H = 0.95 - 1.00 Å and refined as riding with Uiso(H) = 1.2Ueq(C). The components of the two symmetry independent disorder sites refined to 0.2680 (13) and 0.2320 (13). The disorder was modelled by creating two full rings for each component and by using suitable constraints and restraints to give each ring component similar geometries.
The title compound, (I), was synthesized two decades ago (Fréchet et al., 1986) as a mixture of cis and trans isomers starting with a cis and trans mixture of cyclohex-2-ene-1,4-diol to obtain electrophilic character of diols. This compound has been used to obtain a wide variety of thermally and acid labile polymers for a variety of applications (Fréchet et al., 1987; Ericsson & Hult, 1991). We have used the trans isomer of this alcohol for the synthesis of a number of homo and copolycarbonates (Ali et al., 2008).
We report here the
of (I). Figures 1 and 2 show the two non-symmetry related components of disorder for the cyclohexene ring in (I). The crystallograhic inversion related disorder is not shown.For related literature, see: Ali et al. (2008); Ericsson & Hult (1991); Fréchet et al. (1986, 1987); Spek (2003).
Data collection: COLLECT (Nonius, 2002); cell
DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL/PC (Sheldrick, 2001); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 2001).C20H16N2O10 | F(000) = 460 |
Mr = 444.35 | Dx = 1.523 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 9286 reflections |
a = 5.6874 (4) Å | θ = 3–27.5° |
b = 13.4958 (10) Å | µ = 0.13 mm−1 |
c = 12.7017 (5) Å | T = 150 K |
β = 96.453 (4)° | Needle, colourless |
V = 968.76 (11) Å3 | 0.40 × 0.18 × 0.12 mm |
Z = 2 |
Nonius KappaCCD diffractometer | 2222 independent reflections |
Radiation source: fine-focus sealed tube | 1408 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.068 |
Detector resolution: 9 pixels mm-1 | θmax = 27.5°, θmin = 3.0° |
φ scans and ω scans with κ offsets | h = −7→7 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −17→17 |
Tmin = 0.560, Tmax = 0.987 | l = −16→16 |
9286 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.167 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0883P)2 + 0.1379P] where P = (Fo2 + 2Fc2)/3 |
2222 reflections | (Δ/σ)max = 0.001 |
185 parameters | Δρmax = 0.24 e Å−3 |
58 restraints | Δρmin = −0.35 e Å−3 |
C20H16N2O10 | V = 968.76 (11) Å3 |
Mr = 444.35 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 5.6874 (4) Å | µ = 0.13 mm−1 |
b = 13.4958 (10) Å | T = 150 K |
c = 12.7017 (5) Å | 0.40 × 0.18 × 0.12 mm |
β = 96.453 (4)° |
Nonius KappaCCD diffractometer | 2222 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | 1408 reflections with I > 2σ(I) |
Tmin = 0.560, Tmax = 0.987 | Rint = 0.068 |
9286 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 58 restraints |
wR(F2) = 0.167 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.24 e Å−3 |
2222 reflections | Δρmin = −0.35 e Å−3 |
185 parameters |
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 | Occ. (<1) | |
N1 | 0.1105 (3) | 0.66892 (13) | 1.23307 (12) | 0.0413 (4) | |
O1 | 0.2311 (3) | 0.72664 (14) | 1.28816 (11) | 0.0724 (5) | |
O2 | −0.0346 (3) | 0.61480 (13) | 1.26762 (11) | 0.0677 (5) | |
C1 | 0.1364 (3) | 0.66467 (13) | 1.12001 (13) | 0.0337 (4) | |
C2 | −0.0422 (3) | 0.62192 (14) | 1.05264 (14) | 0.0382 (4) | |
H2 | −0.1786 | 0.5955 | 1.0793 | 0.046* | |
C3 | −0.0189 (4) | 0.61836 (14) | 0.94586 (14) | 0.0422 (5) | |
H3 | −0.1399 | 0.5899 | 0.8976 | 0.051* | |
C4 | 0.1818 (4) | 0.65644 (15) | 0.91015 (14) | 0.0431 (5) | |
C5 | 0.3600 (3) | 0.69951 (16) | 0.97755 (15) | 0.0455 (5) | |
H5 | 0.4966 | 0.7254 | 0.9506 | 0.055* | |
C6 | 0.3380 (3) | 0.70468 (15) | 1.08455 (14) | 0.0406 (5) | |
H6 | 0.4573 | 0.7347 | 1.1325 | 0.049* | |
O3 | 0.1941 (3) | 0.65488 (13) | 0.80041 (10) | 0.0582 (4) | |
C7 | 0.3396 (3) | 0.58846 (15) | 0.76418 (14) | 0.0394 (5) | |
O4 | 0.4698 (2) | 0.53485 (11) | 0.81690 (10) | 0.0491 (4) | |
O5 | 0.3066 (3) | 0.59665 (13) | 0.65942 (10) | 0.0551 (4) | |
C8A | 0.4218 (17) | 0.5118 (9) | 0.6065 (8) | 0.0423 (9) | 0.2680 (13) |
H8A | 0.4651 | 0.4583 | 0.6597 | 0.051* | 0.2680 (13) |
C9A | 0.6450 (17) | 0.5568 (7) | 0.5726 (7) | 0.0341 (18) | 0.2680 (13) |
H9A | 0.7567 | 0.5721 | 0.6360 | 0.041* | 0.2680 (13) |
H9B | 0.6059 | 0.6195 | 0.5341 | 0.041* | 0.2680 (13) |
C10A | 0.7618 (16) | 0.4853 (7) | 0.5010 (6) | 0.0509 (19) | 0.2680 (13) |
H10A | 0.9225 | 0.5081 | 0.4897 | 0.061* | 0.2680 (13) |
H10B | 0.7721 | 0.4177 | 0.5314 | 0.061* | 0.2680 (13) |
C11A | 0.5965 (18) | 0.4882 (9) | 0.3987 (9) | 0.0423 (9) | 0.2680 (13) |
H11A | 0.6139 | 0.5519 | 0.3603 | 0.051* | 0.2680 (13) |
C12A | 0.3392 (18) | 0.4672 (7) | 0.4093 (7) | 0.037 (2) | 0.2680 (13) |
H12A | 0.2298 | 0.4543 | 0.3487 | 0.045* | 0.2680 (13) |
C13A | 0.2677 (17) | 0.4674 (6) | 0.5102 (5) | 0.0435 (17) | 0.2680 (13) |
H13A | 0.1188 | 0.4392 | 0.5203 | 0.052* | 0.2680 (13) |
C8B | 0.496 (2) | 0.5532 (8) | 0.6018 (9) | 0.0423 (9) | 0.2320 (13) |
H8B | 0.6551 | 0.5605 | 0.6438 | 0.051* | 0.2320 (13) |
C9B | 0.4298 (19) | 0.4460 (8) | 0.5879 (8) | 0.0341 (18) | 0.2320 (13) |
H9C | 0.2613 | 0.4410 | 0.5587 | 0.041* | 0.2320 (13) |
H9D | 0.4489 | 0.4127 | 0.6578 | 0.041* | 0.2320 (13) |
C10B | 0.5814 (19) | 0.3938 (10) | 0.5141 (8) | 0.0509 (19) | 0.2320 (13) |
H10C | 0.5527 | 0.3214 | 0.5139 | 0.061* | 0.2320 (13) |
H10D | 0.7515 | 0.4062 | 0.5359 | 0.061* | 0.2320 (13) |
C11B | 0.506 (2) | 0.4379 (8) | 0.4055 (9) | 0.0423 (9) | 0.2320 (13) |
H11B | 0.3474 | 0.4124 | 0.3759 | 0.051* | 0.2320 (13) |
C12B | 0.5147 (19) | 0.5479 (9) | 0.3997 (9) | 0.037 (2) | 0.2320 (13) |
H12B | 0.5330 | 0.5814 | 0.3353 | 0.045* | 0.2320 (13) |
C13B | 0.4943 (19) | 0.5999 (9) | 0.4934 (7) | 0.0435 (17) | 0.2320 (13) |
H13B | 0.4777 | 0.6698 | 0.4887 | 0.052* | 0.2320 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0430 (9) | 0.0476 (10) | 0.0351 (8) | −0.0026 (8) | 0.0119 (7) | −0.0027 (7) |
O1 | 0.0743 (11) | 0.1030 (14) | 0.0427 (8) | −0.0408 (10) | 0.0191 (7) | −0.0301 (8) |
O2 | 0.0728 (11) | 0.0881 (13) | 0.0447 (9) | −0.0339 (10) | 0.0181 (7) | 0.0035 (8) |
C1 | 0.0384 (10) | 0.0327 (9) | 0.0311 (9) | 0.0052 (8) | 0.0090 (7) | −0.0006 (7) |
C2 | 0.0388 (10) | 0.0342 (10) | 0.0420 (10) | 0.0021 (8) | 0.0060 (8) | 0.0018 (8) |
C3 | 0.0487 (11) | 0.0407 (11) | 0.0357 (10) | 0.0075 (9) | −0.0021 (8) | −0.0036 (8) |
C4 | 0.0485 (11) | 0.0510 (12) | 0.0305 (9) | 0.0232 (9) | 0.0071 (8) | 0.0028 (8) |
C5 | 0.0383 (11) | 0.0579 (13) | 0.0431 (10) | 0.0087 (9) | 0.0164 (8) | 0.0066 (9) |
C6 | 0.0382 (10) | 0.0470 (11) | 0.0375 (10) | 0.0010 (8) | 0.0080 (7) | −0.0016 (8) |
O3 | 0.0684 (10) | 0.0769 (11) | 0.0302 (7) | 0.0395 (8) | 0.0100 (6) | 0.0045 (6) |
C7 | 0.0377 (10) | 0.0498 (11) | 0.0306 (9) | 0.0040 (9) | 0.0033 (7) | −0.0026 (8) |
O4 | 0.0554 (9) | 0.0584 (9) | 0.0326 (7) | 0.0197 (7) | 0.0006 (6) | −0.0061 (6) |
O5 | 0.0578 (9) | 0.0801 (11) | 0.0278 (7) | 0.0220 (8) | 0.0059 (6) | −0.0007 (6) |
C8A | 0.052 (3) | 0.043 (3) | 0.0314 (14) | −0.0076 (18) | 0.0046 (15) | −0.0078 (17) |
C9A | 0.040 (4) | 0.037 (4) | 0.025 (3) | −0.001 (3) | −0.001 (3) | −0.001 (2) |
C10A | 0.051 (4) | 0.056 (4) | 0.047 (4) | −0.019 (4) | 0.013 (3) | −0.006 (3) |
C11A | 0.052 (3) | 0.043 (3) | 0.0314 (14) | −0.0076 (18) | 0.0046 (15) | −0.0078 (17) |
C12A | 0.037 (4) | 0.041 (4) | 0.032 (4) | 0.002 (3) | −0.002 (3) | 0.004 (3) |
C13A | 0.061 (4) | 0.039 (3) | 0.032 (3) | −0.024 (3) | 0.013 (3) | −0.004 (2) |
C8B | 0.052 (3) | 0.043 (3) | 0.0314 (14) | −0.0076 (18) | 0.0046 (15) | −0.0078 (17) |
C9B | 0.040 (4) | 0.037 (4) | 0.025 (3) | −0.001 (3) | −0.001 (3) | −0.001 (2) |
C10B | 0.051 (4) | 0.056 (4) | 0.047 (4) | −0.019 (4) | 0.013 (3) | −0.006 (3) |
C11B | 0.052 (3) | 0.043 (3) | 0.0314 (14) | −0.0076 (18) | 0.0046 (15) | −0.0078 (17) |
C12B | 0.037 (4) | 0.041 (4) | 0.032 (4) | 0.002 (3) | −0.002 (3) | 0.004 (3) |
C13B | 0.061 (4) | 0.039 (3) | 0.032 (3) | −0.024 (3) | 0.013 (3) | −0.004 (2) |
N1—O1 | 1.208 (2) | C9A—H9A | 0.9900 |
N1—O2 | 1.220 (2) | C10A—C11A | 1.516 (10) |
N1—C1 | 1.461 (2) | C10A—H10A | 0.9900 |
C1—C2 | 1.379 (3) | C10A—H10B | 0.9900 |
C1—C6 | 1.387 (3) | C11A—O5i | 1.500 (10) |
C2—C3 | 1.378 (3) | C11A—C12A | 1.511 (10) |
C2—H2 | 0.9500 | C11A—H11A | 1.0000 |
C3—C4 | 1.374 (3) | C12A—C13A | 1.387 (11) |
C3—H3 | 0.9500 | C12A—H12A | 0.9500 |
C4—C5 | 1.379 (3) | C13A—H13A | 0.9500 |
C4—O3 | 1.403 (2) | C8B—C9B | 1.502 (11) |
C5—C6 | 1.381 (3) | C8B—C13B | 1.513 (10) |
C5—H5 | 0.9500 | C8B—H8B | 1.0000 |
C6—H6 | 0.9500 | C9B—C10B | 1.517 (11) |
O3—C7 | 1.336 (2) | C9B—H9C | 0.9900 |
C7—O4 | 1.187 (2) | C9B—H9D | 0.9900 |
C7—O5 | 1.327 (2) | C10B—C11B | 1.519 (11) |
O5—C8B | 1.491 (10) | C10B—H10C | 0.9900 |
O5—C11Bi | 1.491 (10) | C10B—H10D | 0.9900 |
O5—C11Ai | 1.500 (10) | C11B—C12B | 1.489 (11) |
O5—C8A | 1.515 (9) | C11B—O5i | 1.491 (10) |
C8A—C9A | 1.513 (10) | C11B—H11B | 1.0000 |
C8A—C13A | 1.543 (9) | C12B—C13B | 1.397 (13) |
C8A—H8A | 1.0000 | C12B—H12B | 0.9500 |
C9A—C10A | 1.527 (10) | C13B—H13B | 0.9500 |
O1—N1—O2 | 122.74 (16) | O5i—C11A—C12A | 108.3 (7) |
O1—N1—C1 | 118.76 (16) | O5i—C11A—C10A | 100.1 (7) |
O2—N1—C1 | 118.49 (16) | C12A—C11A—C10A | 115.6 (9) |
C2—C1—C6 | 122.64 (17) | O5i—C11A—H11A | 110.8 |
C2—C1—N1 | 118.54 (16) | C12A—C11A—H11A | 110.8 |
C6—C1—N1 | 118.82 (16) | C10A—C11A—H11A | 110.8 |
C3—C2—C1 | 118.65 (18) | C13A—C12A—C11A | 118.0 (9) |
C3—C2—H2 | 120.7 | C13A—C12A—H12A | 121.0 |
C1—C2—H2 | 120.7 | C11A—C12A—H12A | 121.0 |
C4—C3—C2 | 119.16 (18) | C12A—C13A—C8A | 122.2 (9) |
C4—C3—H3 | 120.4 | C12A—C13A—H13A | 118.9 |
C2—C3—H3 | 120.4 | C8A—C13A—H13A | 118.9 |
C3—C4—C5 | 122.15 (17) | O5—C8B—C9B | 104.4 (9) |
C3—C4—O3 | 117.26 (18) | O5—C8B—C13B | 110.5 (8) |
C5—C4—O3 | 120.50 (19) | C9B—C8B—C13B | 108.5 (10) |
C4—C5—C6 | 119.38 (18) | O5—C8B—H8B | 111.0 |
C4—C5—H5 | 120.3 | C9B—C8B—H8B | 111.0 |
C6—C5—H5 | 120.3 | C13B—C8B—H8B | 111.0 |
C5—C6—C1 | 118.01 (18) | C8B—C9B—C10B | 111.5 (9) |
C5—C6—H6 | 121.0 | C8B—C9B—H9C | 109.3 |
C1—C6—H6 | 121.0 | C10B—C9B—H9C | 109.3 |
C7—O3—C4 | 116.99 (14) | C8B—C9B—H9D | 109.3 |
O4—C7—O5 | 128.71 (18) | C10B—C9B—H9D | 109.3 |
O4—C7—O3 | 125.86 (17) | H9C—C9B—H9D | 108.0 |
O5—C7—O3 | 105.43 (16) | C9B—C10B—C11B | 105.0 (9) |
C7—O5—C8B | 115.5 (5) | C9B—C10B—H10C | 110.7 |
C7—O5—C8A | 111.3 (5) | C11B—C10B—H10C | 110.7 |
C9A—C8A—O5 | 104.0 (8) | C9B—C10B—H10D | 110.7 |
C9A—C8A—C13A | 110.5 (8) | C11B—C10B—H10D | 110.7 |
O5—C8A—C13A | 114.2 (7) | H10C—C10B—H10D | 108.8 |
C9A—C8A—H8A | 109.3 | C12B—C11B—O5i | 104.8 (8) |
O5—C8A—H8A | 109.3 | C12B—C11B—C10B | 115.4 (11) |
C13A—C8A—H8A | 109.3 | O5i—C11B—C10B | 103.6 (8) |
C8A—C9A—C10A | 110.5 (8) | C12B—C11B—H11B | 110.9 |
C8A—C9A—H9A | 109.5 | O5i—C11B—H11B | 110.9 |
C10A—C9A—H9A | 109.5 | C10B—C11B—H11B | 110.9 |
C11A—C10A—C9A | 103.0 (8) | C13B—C12B—C11B | 116.9 (11) |
C11A—C10A—H10A | 111.2 | C13B—C12B—H12B | 121.6 |
C9A—C10A—H10A | 111.2 | C11B—C12B—H12B | 121.6 |
C11A—C10A—H10B | 111.2 | C12B—C13B—C8B | 125.0 (11) |
C9A—C10A—H10B | 111.2 | C12B—C13B—H13B | 117.5 |
H10A—C10A—H10B | 109.1 | C8B—C13B—H13B | 117.5 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C20H16N2O10 |
Mr | 444.35 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 150 |
a, b, c (Å) | 5.6874 (4), 13.4958 (10), 12.7017 (5) |
β (°) | 96.453 (4) |
V (Å3) | 968.76 (11) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.13 |
Crystal size (mm) | 0.40 × 0.18 × 0.12 |
Data collection | |
Diffractometer | Nonius KappaCCD |
Absorption correction | Multi-scan (SORTAV; Blessing, 1995) |
Tmin, Tmax | 0.560, 0.987 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9286, 2222, 1408 |
Rint | 0.068 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.167, 1.05 |
No. of reflections | 2222 |
No. of parameters | 185 |
No. of restraints | 58 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.35 |
Computer programs: COLLECT (Nonius, 2002), DENZO-SMN (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXTL/PC (Sheldrick, 2001), PLATON (Spek, 2003).
Acknowledgements
The authors acknowledge funding from the Higher Education Commission (HEC) of Pakistan, Materials and Manufacturing Ontario (MMO), Canada, NSERC Canada and the University of Toronto.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The title compound, (I), was synthesized two decades ago (Fréchet et al., 1986) as a mixture of cis and trans isomers starting with a cis and trans mixture of cyclohex-2-ene-1,4-diol to obtain electrophilic character of diols. This compound has been used to obtain a wide variety of thermally and acid labile polymers for a variety of applications (Fréchet et al., 1987; Ericsson & Hult, 1991). We have used the trans isomer of this alcohol for the synthesis of a number of homo and copolycarbonates (Ali et al., 2008).
We report here the crystal structure of (I). Figures 1 and 2 show the two non-symmetry related components of disorder for the cyclohexene ring in (I). The crystallograhic inversion related disorder is not shown.