organic compounds
trans-Cyclohexane-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
In the title 20H18N2O10, there are two independent molecules, both of which lie on crystallographic inversion centres. In one molecule the 4-nitrophenyl dicarbonate groups are substituted in equatorial (Aeq) positions of the chair-form cyclohexane ring while in the other molecule the substitution is axial (Bax). The dihedral angles between the atoms of the symmetry-unique carbonate group (O=CO2—) and benzene ring for each molecule are 47.3 (1)° for Aeq and 11.7 (2)° for Bax. In Bax, this facilitates the formation of a weak intramolecular C—H⋯O hydrogen bond, while the packing is stabilized by weak intermolecular C—H⋯O interactions.
CExperimental
Crystal data
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Refinement
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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/S1600536807066007/hb2675sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807066007/hb2675Isup2.hkl
A solution of 4-nitrophenylchloroformate (5.64 g, 28.0 mmol) in dry dichloromethane (40 ml) was added dropwise via a 100 ml separating funnel into a solution of cyclohexane-1,4-diol (cis and trans isomers) (1.63 g, 14.0 mmol) in anhydrous pyridine (2.15 g, 2.2 ml, 27.1 mmol) and dry dichloromethane (20 ml) in a 250 ml round-bottom flask. A white suspension appeared which was allowed to stir gently at room temperature for 16 h. After this time more dry dichloromethane (40 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 (40 ml). The reaction mixture was transferred to a separating funnel (500 ml), and the lower organic phase was removed. The aqueous phase was washed with dichloromethane (30 ml × 2), and the dichloromethane solutions were combined. These were then washed with deionized water (30 ml × 2), a 1.0% solution of acetic acid (50 ml × 2) and once more with deionized water (40 ml × 2), and then dried over anhydrous magnesium sulfate and filtered. After filtration, the solvent was removed by rotary evaporator. 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 (6.2 g, 84.0%) as a white solid. For recrystallization, the solid was dissolved in 95% EtOH (50 ml) at 358 K, after 40 minutes some of the solid (about 40%) remained undissolved. The warm solution was filtered and the EtOH-insoluble solid was recovered from the filter paper and dissolved in dichloromethane. Pale yellow plates of (I) were obtained by slow evaporation of solvent at room temperature.
The H 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 synthesis of title compound is similar to that of cyclohex-2-ene-1,4-diylbis(4-nitrophenyl)dicarbonate (Ali et al., 2008). Here, we used a mixture of cis and trans isomers of cyclohexane-1,4-diol. The trans isomer has been separated from the mixture of cis and trans isomers. Most of the trans isomer remained undissolved in EtOH during the recrystallization at 358 K, after 40 minutes. Pale yellow plates of (I) were obtained after solubilizing this EtOH insoluble solid in dichloromethane. The molecular structure is illustrated in Figs. 1 and 2, showing that one of the two asymmetric molecules possesses equatorial substituents and the other axial. Within the latter, a weak C—H···O interaction (Table 1) occurs. Further C—H···O links help to establish the packing.
For related literature, see: Ali et al. (2008); 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).C20H18N2O10 | Z = 2 |
Mr = 446.36 | F(000) = 464 |
Triclinic, P1 | Dx = 1.521 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.6804 (14) Å | Cell parameters from 7088 reflections |
b = 11.6548 (18) Å | θ = 2.7–25.2° |
c = 12.3092 (11) Å | µ = 0.12 mm−1 |
α = 63.201 (8)° | T = 150 K |
β = 87.254 (10)° | Plate, pale yellow |
γ = 82.310 (7)° | 0.22 × 0.20 × 0.08 mm |
V = 974.6 (3) Å3 |
Nonius KappaCCD diffractometer | 3355 independent reflections |
Radiation source: fine-focus sealed tube | 1633 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.080 |
Detector resolution: 9 pixels mm-1 | θmax = 25.2°, θmin = 2.7° |
φ scans and ω scans with κ offsets | h = −9→9 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −12→13 |
Tmin = 0.768, Tmax = 0.996 | l = −14→14 |
7088 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)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.190 | H-atom parameters constrained |
S = 0.96 | w = 1/[σ2(Fo2) + (0.0923P)2] where P = (Fo2 + 2Fc2)/3 |
3355 reflections | (Δ/σ)max < 0.001 |
289 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C20H18N2O10 | γ = 82.310 (7)° |
Mr = 446.36 | V = 974.6 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.6804 (14) Å | Mo Kα radiation |
b = 11.6548 (18) Å | µ = 0.12 mm−1 |
c = 12.3092 (11) Å | T = 150 K |
α = 63.201 (8)° | 0.22 × 0.20 × 0.08 mm |
β = 87.254 (10)° |
Nonius KappaCCD diffractometer | 3355 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | 1633 reflections with I > 2σ(I) |
Tmin = 0.768, Tmax = 0.996 | Rint = 0.080 |
7088 measured reflections |
R[F2 > 2σ(F2)] = 0.063 | 0 restraints |
wR(F2) = 0.190 | H-atom parameters constrained |
S = 0.96 | Δρmax = 0.30 e Å−3 |
3355 reflections | Δρmin = −0.27 e Å−3 |
289 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 | ||
O1A | 0.1429 (4) | 0.0985 (3) | 0.2676 (2) | 0.0517 (8) | |
O2A | 0.4182 (4) | −0.0092 (3) | 0.2921 (2) | 0.0504 (8) | |
O3A | 0.3173 (4) | 0.1684 (3) | 0.1182 (2) | 0.0524 (8) | |
O4A | 0.9007 (4) | 0.1716 (3) | −0.2527 (3) | 0.0685 (10) | |
O5A | 1.0631 (5) | 0.1300 (3) | −0.0977 (3) | 0.0690 (10) | |
N1A | 0.9198 (6) | 0.1542 (3) | −0.1481 (4) | 0.0498 (10) | |
C1A | −0.1660 (6) | −0.0576 (4) | 0.5216 (3) | 0.0495 (12) | |
H1A1 | −0.1245 | −0.1509 | 0.5502 | 0.059* | |
H1A2 | −0.2960 | −0.0463 | 0.5211 | 0.059* | |
C2A | −0.1003 (6) | 0.0194 (4) | 0.3939 (3) | 0.0513 (12) | |
H2A1 | −0.1389 | −0.0145 | 0.3396 | 0.062* | |
H2A2 | −0.1520 | 0.1112 | 0.3624 | 0.062* | |
C3A | 0.0979 (6) | 0.0112 (4) | 0.3927 (3) | 0.0474 (12) | |
H3A | 0.1518 | −0.0796 | 0.4145 | 0.057* | |
C4A | 0.3057 (6) | 0.0763 (4) | 0.2341 (4) | 0.0453 (11) | |
C5A | 0.4739 (6) | 0.1635 (4) | 0.0559 (3) | 0.0409 (11) | |
C6A | 0.6345 (6) | 0.1517 (4) | 0.1054 (4) | 0.0476 (12) | |
H6AA | 0.6442 | 0.1459 | 0.1844 | 0.057* | |
C7A | 0.7824 (6) | 0.1483 (4) | 0.0383 (4) | 0.0478 (11) | |
H7AA | 0.8962 | 0.1381 | 0.0709 | 0.057* | |
C8A | 0.7621 (6) | 0.1599 (4) | −0.0766 (3) | 0.0402 (10) | |
C9A | 0.6019 (6) | 0.1746 (4) | −0.1267 (3) | 0.0459 (11) | |
H9AA | 0.5926 | 0.1831 | −0.2068 | 0.055* | |
C10A | 0.4527 (6) | 0.1771 (4) | −0.0601 (3) | 0.0455 (11) | |
H10A | 0.3391 | 0.1878 | −0.0932 | 0.055* | |
O1B | 0.9940 (4) | 0.5357 (3) | 0.1688 (2) | 0.0493 (8) | |
O2B | 0.9203 (4) | 0.3799 (3) | 0.3498 (2) | 0.0568 (9) | |
O3B | 0.8673 (4) | 0.5951 (3) | 0.2963 (2) | 0.0486 (8) | |
O4B | 0.4719 (5) | 0.5191 (3) | 0.7792 (3) | 0.0708 (11) | |
O5B | 0.4665 (5) | 0.7279 (4) | 0.6849 (3) | 0.0731 (11) | |
N1B | 0.5072 (5) | 0.6198 (4) | 0.6918 (3) | 0.0527 (10) | |
C1B | 0.8165 (6) | 0.4921 (4) | −0.0214 (4) | 0.0507 (12) | |
H1B1 | 0.7325 | 0.4509 | −0.0465 | 0.061* | |
H1B2 | 0.7480 | 0.5565 | 0.0008 | 0.061* | |
C2B | 0.9217 (6) | 0.3884 (4) | 0.0905 (3) | 0.0500 (12) | |
H2B1 | 0.8409 | 0.3535 | 0.1597 | 0.060* | |
H2B2 | 0.9730 | 0.3162 | 0.0728 | 0.060* | |
C3B | 1.0669 (6) | 0.4393 (4) | 0.1269 (3) | 0.0497 (12) | |
H3B | 1.1392 | 0.3659 | 0.1938 | 0.060* | |
C4B | 0.9251 (6) | 0.4897 (4) | 0.2793 (4) | 0.0474 (11) | |
C5B | 0.7791 (6) | 0.5888 (4) | 0.4005 (3) | 0.0425 (11) | |
C6B | 0.7732 (6) | 0.4775 (4) | 0.5097 (3) | 0.0457 (11) | |
H6BA | 0.8299 | 0.3960 | 0.5189 | 0.055* | |
C7B | 0.6813 (6) | 0.4894 (4) | 0.6054 (4) | 0.0473 (11) | |
H7BA | 0.6735 | 0.4149 | 0.6810 | 0.057* | |
C8B | 0.6022 (6) | 0.6085 (4) | 0.5905 (3) | 0.0412 (10) | |
C9B | 0.6109 (6) | 0.7178 (4) | 0.4819 (3) | 0.0439 (11) | |
H9BA | 0.5554 | 0.7996 | 0.4727 | 0.053* | |
C10B | 0.7007 (6) | 0.7072 (4) | 0.3872 (3) | 0.0405 (10) | |
H10B | 0.7085 | 0.7822 | 0.3120 | 0.049* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.052 (2) | 0.0532 (18) | 0.0391 (16) | 0.0002 (15) | 0.0040 (14) | −0.0132 (14) |
O2A | 0.052 (2) | 0.0445 (17) | 0.0441 (16) | 0.0074 (16) | −0.0042 (15) | −0.0133 (13) |
O3A | 0.055 (2) | 0.0517 (17) | 0.0347 (16) | 0.0048 (15) | 0.0035 (14) | −0.0093 (14) |
O4A | 0.061 (3) | 0.087 (2) | 0.072 (2) | −0.0174 (19) | 0.0189 (18) | −0.048 (2) |
O5A | 0.045 (2) | 0.064 (2) | 0.078 (2) | −0.0100 (18) | 0.0049 (19) | −0.0146 (17) |
N1A | 0.047 (3) | 0.040 (2) | 0.059 (3) | −0.0088 (19) | 0.004 (2) | −0.0180 (18) |
C1A | 0.051 (3) | 0.052 (3) | 0.045 (2) | −0.015 (2) | 0.003 (2) | −0.019 (2) |
C2A | 0.056 (3) | 0.062 (3) | 0.039 (2) | −0.008 (2) | −0.001 (2) | −0.025 (2) |
C3A | 0.055 (3) | 0.051 (3) | 0.036 (2) | −0.007 (2) | 0.001 (2) | −0.019 (2) |
C4A | 0.049 (3) | 0.046 (3) | 0.044 (3) | −0.006 (2) | 0.008 (2) | −0.025 (2) |
C5A | 0.043 (3) | 0.035 (2) | 0.041 (2) | −0.003 (2) | 0.010 (2) | −0.0155 (18) |
C6A | 0.055 (3) | 0.048 (3) | 0.042 (2) | −0.003 (2) | −0.007 (2) | −0.022 (2) |
C7A | 0.043 (3) | 0.048 (3) | 0.052 (3) | −0.007 (2) | −0.005 (2) | −0.021 (2) |
C8A | 0.042 (3) | 0.032 (2) | 0.044 (2) | −0.0007 (19) | 0.002 (2) | −0.0166 (18) |
C9A | 0.054 (3) | 0.045 (2) | 0.035 (2) | −0.010 (2) | −0.001 (2) | −0.0141 (19) |
C10A | 0.040 (3) | 0.050 (3) | 0.039 (2) | −0.008 (2) | 0.000 (2) | −0.0126 (19) |
O1B | 0.059 (2) | 0.0453 (16) | 0.0435 (17) | −0.0044 (15) | 0.0073 (14) | −0.0209 (13) |
O2B | 0.079 (3) | 0.0435 (19) | 0.0430 (17) | −0.0046 (16) | 0.0087 (15) | −0.0169 (15) |
O3B | 0.063 (2) | 0.0411 (17) | 0.0404 (16) | −0.0016 (15) | 0.0082 (14) | −0.0194 (13) |
O4B | 0.077 (3) | 0.075 (2) | 0.0455 (19) | −0.004 (2) | 0.0170 (17) | −0.0174 (17) |
O5B | 0.084 (3) | 0.072 (2) | 0.079 (2) | −0.009 (2) | 0.0228 (19) | −0.050 (2) |
N1B | 0.048 (3) | 0.064 (3) | 0.048 (2) | −0.003 (2) | 0.0061 (18) | −0.029 (2) |
C1B | 0.051 (3) | 0.049 (3) | 0.054 (3) | −0.002 (2) | 0.005 (2) | −0.027 (2) |
C2B | 0.066 (3) | 0.045 (3) | 0.042 (2) | −0.009 (2) | 0.009 (2) | −0.022 (2) |
C3B | 0.066 (3) | 0.042 (2) | 0.042 (2) | −0.003 (2) | 0.004 (2) | −0.021 (2) |
C4B | 0.060 (3) | 0.043 (3) | 0.036 (2) | −0.008 (2) | −0.001 (2) | −0.014 (2) |
C5B | 0.046 (3) | 0.047 (3) | 0.035 (2) | −0.007 (2) | −0.0012 (19) | −0.0187 (19) |
C6B | 0.048 (3) | 0.039 (2) | 0.051 (3) | 0.002 (2) | 0.000 (2) | −0.022 (2) |
C7B | 0.048 (3) | 0.047 (3) | 0.041 (2) | −0.008 (2) | 0.001 (2) | −0.015 (2) |
C8B | 0.038 (3) | 0.046 (3) | 0.040 (2) | −0.005 (2) | 0.0024 (19) | −0.020 (2) |
C9B | 0.043 (3) | 0.043 (2) | 0.050 (3) | −0.003 (2) | −0.003 (2) | −0.025 (2) |
C10B | 0.045 (3) | 0.041 (2) | 0.037 (2) | −0.010 (2) | 0.0005 (19) | −0.0180 (19) |
O1A—C4A | 1.327 (5) | O1B—C4B | 1.328 (5) |
O1A—C3A | 1.469 (4) | O1B—C3B | 1.472 (5) |
O2A—C4A | 1.199 (5) | O2B—C4B | 1.184 (5) |
O3A—C4A | 1.352 (5) | O3B—C4B | 1.352 (5) |
O3A—C5A | 1.404 (5) | O3B—C5B | 1.398 (5) |
O4A—N1A | 1.223 (4) | O4B—N1B | 1.236 (4) |
O5A—N1A | 1.224 (5) | O5B—N1B | 1.222 (5) |
N1A—C8A | 1.475 (5) | N1B—C8B | 1.463 (5) |
C1A—C2A | 1.518 (5) | C1B—C3Bii | 1.507 (5) |
C1A—C3Ai | 1.525 (6) | C1B—C2B | 1.535 (5) |
C1A—H1A1 | 0.9900 | C1B—H1B1 | 0.9900 |
C1A—H1A2 | 0.9900 | C1B—H1B2 | 0.9900 |
C2A—C3A | 1.512 (6) | C2B—C3B | 1.503 (6) |
C2A—H2A1 | 0.9900 | C2B—H2B1 | 0.9900 |
C2A—H2A2 | 0.9900 | C2B—H2B2 | 0.9900 |
C3A—C1Ai | 1.525 (6) | C3B—C1Bii | 1.507 (5) |
C3A—H3A | 1.0000 | C3B—H3B | 1.0000 |
C5A—C6A | 1.365 (6) | C5B—C10B | 1.370 (5) |
C5A—C10A | 1.379 (6) | C5B—C6B | 1.388 (5) |
C6A—C7A | 1.379 (6) | C6B—C7B | 1.395 (6) |
C6A—H6AA | 0.9500 | C6B—H6BA | 0.9500 |
C7A—C8A | 1.373 (5) | C7B—C8B | 1.373 (6) |
C7A—H7AA | 0.9500 | C7B—H7BA | 0.9500 |
C8A—C9A | 1.358 (6) | C8B—C9B | 1.375 (5) |
C9A—C10A | 1.381 (6) | C9B—C10B | 1.372 (5) |
C9A—H9AA | 0.9500 | C9B—H9BA | 0.9500 |
C10A—H10A | 0.9500 | C10B—H10B | 0.9500 |
C4A—O1A—C3A | 116.0 (3) | C4B—O1B—C3B | 116.4 (3) |
C4A—O3A—C5A | 118.0 (3) | C4B—O3B—C5B | 123.4 (3) |
O4A—N1A—O5A | 123.8 (4) | O5B—N1B—O4B | 123.8 (4) |
O4A—N1A—C8A | 118.7 (4) | O5B—N1B—C8B | 118.3 (4) |
O5A—N1A—C8A | 117.5 (4) | O4B—N1B—C8B | 117.8 (4) |
C2A—C1A—C3Ai | 109.7 (3) | C3Bii—C1B—C2B | 112.3 (4) |
C2A—C1A—H1A1 | 109.7 | C3Bii—C1B—H1B1 | 109.1 |
C3Ai—C1A—H1A1 | 109.7 | C2B—C1B—H1B1 | 109.1 |
C2A—C1A—H1A2 | 109.7 | C3Bii—C1B—H1B2 | 109.1 |
C3Ai—C1A—H1A2 | 109.7 | C2B—C1B—H1B2 | 109.1 |
H1A1—C1A—H1A2 | 108.2 | H1B1—C1B—H1B2 | 107.9 |
C3A—C2A—C1A | 111.1 (3) | C3B—C2B—C1B | 112.9 (4) |
C3A—C2A—H2A1 | 109.4 | C3B—C2B—H2B1 | 109.0 |
C1A—C2A—H2A1 | 109.4 | C1B—C2B—H2B1 | 109.0 |
C3A—C2A—H2A2 | 109.4 | C3B—C2B—H2B2 | 109.0 |
C1A—C2A—H2A2 | 109.4 | C1B—C2B—H2B2 | 109.0 |
H2A1—C2A—H2A2 | 108.0 | H2B1—C2B—H2B2 | 107.8 |
O1A—C3A—C2A | 105.7 (3) | O1B—C3B—C2B | 110.5 (4) |
O1A—C3A—C1Ai | 108.5 (3) | O1B—C3B—C1Bii | 106.1 (3) |
C2A—C3A—C1Ai | 111.9 (4) | C2B—C3B—C1Bii | 111.9 (3) |
O1A—C3A—H3A | 110.2 | O1B—C3B—H3B | 109.4 |
C2A—C3A—H3A | 110.2 | C2B—C3B—H3B | 109.4 |
C1Ai—C3A—H3A | 110.2 | C1Bii—C3B—H3B | 109.4 |
O2A—C4A—O1A | 127.8 (4) | O2B—C4B—O1B | 127.6 (4) |
O2A—C4A—O3A | 126.7 (4) | O2B—C4B—O3B | 127.0 (4) |
O1A—C4A—O3A | 105.5 (4) | O1B—C4B—O3B | 105.3 (3) |
C6A—C5A—C10A | 122.8 (4) | C10B—C5B—C6B | 121.5 (4) |
C6A—C5A—O3A | 122.0 (4) | C10B—C5B—O3B | 113.0 (3) |
C10A—C5A—O3A | 115.1 (4) | C6B—C5B—O3B | 125.5 (4) |
C5A—C6A—C7A | 118.6 (4) | C5B—C6B—C7B | 117.8 (4) |
C5A—C6A—H6AA | 120.7 | C5B—C6B—H6BA | 121.1 |
C7A—C6A—H6AA | 120.7 | C7B—C6B—H6BA | 121.1 |
C8A—C7A—C6A | 118.8 (4) | C8B—C7B—C6B | 120.1 (4) |
C8A—C7A—H7AA | 120.6 | C8B—C7B—H7BA | 120.0 |
C6A—C7A—H7AA | 120.6 | C6B—C7B—H7BA | 120.0 |
C9A—C8A—C7A | 122.5 (4) | C7B—C8B—C9B | 121.2 (4) |
C9A—C8A—N1A | 118.4 (4) | C7B—C8B—N1B | 119.6 (3) |
C7A—C8A—N1A | 119.0 (4) | C9B—C8B—N1B | 119.2 (4) |
C8A—C9A—C10A | 119.3 (4) | C10B—C9B—C8B | 119.2 (4) |
C8A—C9A—H9AA | 120.3 | C10B—C9B—H9BA | 120.4 |
C10A—C9A—H9AA | 120.3 | C8B—C9B—H9BA | 120.4 |
C5A—C10A—C9A | 117.9 (4) | C5B—C10B—C9B | 120.2 (3) |
C5A—C10A—H10A | 121.0 | C5B—C10B—H10B | 119.9 |
C9A—C10A—H10A | 121.0 | C9B—C10B—H10B | 119.9 |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x+2, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C10A—H10A···O5Aiii | 0.95 | 2.32 | 3.205 (6) | 155 |
C6B—H6BA···O2B | 0.95 | 2.24 | 2.812 (5) | 118 |
C9B—H9BA···O2Aiv | 0.95 | 2.48 | 3.184 (5) | 131 |
Symmetry codes: (iii) x−1, y, z; (iv) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C20H18N2O10 |
Mr | 446.36 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 150 |
a, b, c (Å) | 7.6804 (14), 11.6548 (18), 12.3092 (11) |
α, β, γ (°) | 63.201 (8), 87.254 (10), 82.310 (7) |
V (Å3) | 974.6 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.22 × 0.20 × 0.08 |
Data collection | |
Diffractometer | Nonius KappaCCD |
Absorption correction | Multi-scan (SORTAV; Blessing, 1995) |
Tmin, Tmax | 0.768, 0.996 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7088, 3355, 1633 |
Rint | 0.080 |
(sin θ/λ)max (Å−1) | 0.600 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.063, 0.190, 0.96 |
No. of reflections | 3355 |
No. of parameters | 289 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.27 |
Computer programs: COLLECT (Nonius, 2002), DENZO-SMN (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXTL/PC (Sheldrick, 2001), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C10A—H10A···O5Ai | 0.95 | 2.32 | 3.205 (6) | 155 |
C6B—H6BA···O2B | 0.95 | 2.24 | 2.812 (5) | 118 |
C9B—H9BA···O2Aii | 0.95 | 2.48 | 3.184 (5) | 131 |
Symmetry codes: (i) x−1, y, z; (ii) x, y+1, z. |
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
Ali, S. N., Begum, S., Winnik, S. A. & Lough, A. J. (2008). Acta Cryst. E64, o281. Web of Science CrossRef IUCr Journals Google Scholar
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Nonius (2002). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2001). SHELXTL/PC. Version 6.1. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
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The synthesis of title compound is similar to that of cyclohex-2-ene-1,4-diylbis(4-nitrophenyl)dicarbonate (Ali et al., 2008). Here, we used a mixture of cis and trans isomers of cyclohexane-1,4-diol. The trans isomer has been separated from the mixture of cis and trans isomers. Most of the trans isomer remained undissolved in EtOH during the recrystallization at 358 K, after 40 minutes. Pale yellow plates of (I) were obtained after solubilizing this EtOH insoluble solid in dichloromethane. The molecular structure is illustrated in Figs. 1 and 2, showing that one of the two asymmetric molecules possesses equatorial substituents and the other axial. Within the latter, a weak C—H···O interaction (Table 1) occurs. Further C—H···O links help to establish the packing.