Acta Cryst. (2012). E68, o45 [ doi:10.1107/S1600536811051993 ]
In the title compound, C22H21ClO2, the oxolane ring adopts a twisted conformation. The dihedral angles between the mean plane of the oxolane ring and the mean planes of the 4-chlorophenyl, phenyl and cyclopentenyl rings are 71.81 (18), 76.9 (18) and 82.08 (18)°, respectively.
To a stirred solution of 1-(4-hydroxy-4-phenylbut-1-ynyl)cyclopentanol (0.31 mmol) and 4-Chlorobenzaldehyde (0.37 mmol) in dry diethyl ether (3.0 ml) was added slowly TMSOTf (0.93 mmol) for 10 min and stirred for 1 h at -78°C. The mixture was allowed to warm to room temperature slowly for 3 h. The mixture was stirred at room temperature for additional 1–2 h until the completion of reaction. The reaction mixture was quenched with saturated aqueous NaHCO3 and diluted with 10 ml of diethyl ether. The organic solution was washed with water and brine, and the organic layer was dried over MgSO4, filtered, concentrated and purification by silica gel column chromatography to afford the title compound (54%) as a yellow crystal.
All hydrogen atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.98 Å and Uiso(H) = 1.2 or 1.5 Ueq(C). Rotating group model was applied for the methyl groups.
Data collection: RAPID-AUTO (Rigaku, 2006); cell refinement: RAPID-AUTO (Rigaku, 2006); data reduction: RAPID-AUTO (Rigaku, 2006); program(s) used to solve structure: Il Milione (Burla et al., 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).
![[Figure 1]](./go2037fig1thm.gif)
| Fig. 1. The structure of the title compound, with displacement ellipsoids drawn at the 50% probability level and H atoms with arbitrary radius. |
| C22H21ClO2 | F(000) = 744.00 |
| Mr = 352.86 | Dx = 1.259 Mg m−3 |
| Monoclinic, P21/n | Cu Kα radiation, λ = 1.54187 Å |
| Hall symbol: -P 2yn | Cell parameters from 12997 reflections |
| a = 5.7575 (6) Å | θ = 3.1–68.3° |
| b = 11.3547 (12) Å | µ = 1.90 mm−1 |
| c = 28.554 (3) Å | T = 296 K |
| β = 94.442 (8)° | Needle, yellow |
| V = 1861.1 (4) Å3 | 0.50 × 0.20 × 0.20 mm |
| Z = 4 |
| Rigaku R-AXIS RAPID diffractometer | 2012 reflections with F2 > 2σ(F2) |
| Detector resolution: 10.000 pixels mm-1 | Rint = 0.073 |
| ω scans | θmax = 68.2° |
| Absorption correction: multi-scan (ABSCOR; Rigaku, 1995) | h = −6→6 |
| Tmin = 0.301, Tmax = 0.684 | k = −13→13 |
| 18544 measured reflections | l = −34→34 |
| 3363 independent reflections |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.139 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.05 | w = 1/[σ2(Fo2) + (0.0568P)2 + 0.1808P] where P = (Fo2 + 2Fc2)/3 |
| 3363 reflections | (Δ/σ)max = 0.001 |
| 230 parameters | Δρmax = 0.20 e Å−3 |
| 0 restraints | Δρmin = −0.19 e Å−3 |
| Primary atom site location: structure-invariant direct methods |
| C22H21ClO2 | V = 1861.1 (4) Å3 |
| Mr = 352.86 | Z = 4 |
| Monoclinic, P21/n | Cu Kα radiation |
| a = 5.7575 (6) Å | µ = 1.90 mm−1 |
| b = 11.3547 (12) Å | T = 296 K |
| c = 28.554 (3) Å | 0.50 × 0.20 × 0.20 mm |
| β = 94.442 (8)° |
| Rigaku R-AXIS RAPID diffractometer | 3363 independent reflections |
| Absorption correction: multi-scan (ABSCOR; Rigaku, 1995) | 2012 reflections with F2 > 2σ(F2) |
| Tmin = 0.301, Tmax = 0.684 | Rint = 0.073 |
| 18544 measured reflections | θmax = 68.2° |
| R[F2 > 2σ(F2)] = 0.051 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.139 | Δρmax = 0.20 e Å−3 |
| S = 1.05 | Δρmin = −0.19 e Å−3 |
| 3363 reflections | Absolute structure: ? |
| 230 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
| x | y | z | Uiso*/Ueq | ||
| Cl(1) | 0.34139 (17) | 0.11812 (7) | 0.53247 (3) | 0.1065 (4) | |
| O(1) | 0.2994 (3) | 0.37307 (13) | 0.74183 (5) | 0.0597 (5) | |
| O(2) | 0.6450 (3) | 0.53421 (16) | 0.66245 (6) | 0.0763 (6) | |
| C(2) | 0.1844 (5) | 0.4198 (2) | 0.70022 (8) | 0.0574 (7) | |
| C(3) | 0.2806 (5) | 0.5488 (2) | 0.69627 (8) | 0.0561 (7) | |
| C(4) | 0.4071 (5) | 0.5703 (3) | 0.74448 (8) | 0.0700 (8) | |
| C(5) | 0.3328 (5) | 0.4685 (3) | 0.77457 (8) | 0.0602 (7) | |
| C(6) | 0.5050 (5) | 0.4344 (2) | 0.81393 (8) | 0.0541 (6) | |
| C(7) | 0.7050 (5) | 0.3738 (3) | 0.80578 (10) | 0.0682 (8) | |
| C(8) | 0.8695 (5) | 0.3488 (3) | 0.84223 (12) | 0.0802 (9) | |
| C(9) | 0.8361 (6) | 0.3839 (3) | 0.88696 (11) | 0.0805 (9) | |
| C(10) | 0.6385 (6) | 0.4435 (3) | 0.89575 (9) | 0.0795 (9) | |
| C(11) | 0.4730 (5) | 0.4682 (3) | 0.85944 (9) | 0.0668 (7) | |
| C(12) | 0.2209 (5) | 0.3392 (2) | 0.65941 (8) | 0.0526 (6) | |
| C(13) | 0.0550 (5) | 0.3341 (3) | 0.62177 (9) | 0.0628 (7) | |
| C(14) | 0.0916 (5) | 0.2667 (3) | 0.58285 (9) | 0.0713 (8) | |
| C(15) | 0.2948 (6) | 0.2045 (3) | 0.58140 (9) | 0.0680 (8) | |
| C(16) | 0.4618 (5) | 0.2066 (3) | 0.61850 (10) | 0.0697 (8) | |
| C(17) | 0.4230 (5) | 0.2737 (2) | 0.65745 (9) | 0.0632 (7) | |
| C(18) | 0.4382 (5) | 0.5586 (2) | 0.65654 (8) | 0.0549 (6) | |
| C(19) | 0.3382 (5) | 0.5935 (2) | 0.60977 (8) | 0.0523 (6) | |
| C(20) | 0.1393 (5) | 0.6481 (3) | 0.59902 (9) | 0.0667 (8) | |
| C(21) | 0.1054 (6) | 0.6755 (3) | 0.54765 (9) | 0.0881 (10) | |
| C(22) | 0.3045 (6) | 0.6163 (4) | 0.52732 (10) | 0.0999 (11) | |
| C(23) | 0.4688 (5) | 0.5744 (3) | 0.56742 (9) | 0.0829 (9) | |
| H(2) | 0.0171 | 0.4240 | 0.7043 | 0.0689* | |
| H(3) | 0.1505 | 0.6041 | 0.6912 | 0.0673* | |
| H(4A) | 0.5746 | 0.5702 | 0.7426 | 0.0840* | |
| H(4B) | 0.3612 | 0.6451 | 0.7573 | 0.0840* | |
| H(5) | 0.1839 | 0.4877 | 0.7872 | 0.0723* | |
| H(7) | 0.7295 | 0.3495 | 0.7755 | 0.0818* | |
| H(8) | 1.0039 | 0.3077 | 0.8363 | 0.0963* | |
| H(9) | 0.9478 | 0.3673 | 0.9113 | 0.0966* | |
| H(10) | 0.6151 | 0.4674 | 0.9262 | 0.0954* | |
| H(11) | 0.3380 | 0.5083 | 0.8657 | 0.0802* | |
| H(13) | −0.0827 | 0.3765 | 0.6227 | 0.0753* | |
| H(14) | −0.0211 | 0.2635 | 0.5577 | 0.0855* | |
| H(16) | 0.5987 | 0.1636 | 0.6174 | 0.0836* | |
| H(17) | 0.5345 | 0.2749 | 0.6828 | 0.0758* | |
| H(21A) | −0.0419 | 0.6444 | 0.5342 | 0.1057* | |
| H(21B) | 0.1090 | 0.7598 | 0.5423 | 0.1057* | |
| H(22A) | 0.3833 | 0.6710 | 0.5078 | 0.1199* | |
| H(22B) | 0.2495 | 0.5501 | 0.5081 | 0.1199* | |
| H(23A) | 0.5063 | 0.4918 | 0.5638 | 0.0994* | |
| H(23B) | 0.6120 | 0.6198 | 0.5694 | 0.0994* | |
| H(20) | 0.033 (5) | 0.672 (3) | 0.6215 (9) | 0.086 (9)* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl(1) | 0.1507 (9) | 0.0956 (7) | 0.0744 (5) | 0.0158 (6) | 0.0156 (5) | −0.0156 (4) |
| O(1) | 0.0594 (12) | 0.0608 (11) | 0.0580 (10) | −0.0031 (9) | −0.0002 (8) | 0.0051 (8) |
| O(2) | 0.0438 (12) | 0.0850 (14) | 0.1001 (14) | 0.0143 (10) | 0.0048 (10) | 0.0100 (11) |
| C(2) | 0.0435 (15) | 0.0749 (17) | 0.0541 (14) | 0.0051 (13) | 0.0051 (12) | 0.0053 (12) |
| C(3) | 0.0554 (16) | 0.0592 (15) | 0.0541 (14) | 0.0195 (13) | 0.0067 (12) | 0.0033 (11) |
| C(4) | 0.091 (2) | 0.0526 (15) | 0.0655 (16) | 0.0113 (15) | −0.0014 (15) | −0.0010 (12) |
| C(5) | 0.0540 (17) | 0.0693 (17) | 0.0580 (15) | 0.0132 (13) | 0.0085 (13) | −0.0031 (13) |
| C(6) | 0.0498 (16) | 0.0577 (14) | 0.0546 (14) | 0.0049 (12) | 0.0032 (12) | 0.0053 (11) |
| C(7) | 0.0614 (19) | 0.0715 (18) | 0.0712 (17) | 0.0147 (15) | 0.0019 (14) | 0.0040 (14) |
| C(8) | 0.063 (2) | 0.0660 (18) | 0.109 (3) | 0.0128 (15) | −0.0068 (18) | 0.0108 (17) |
| C(9) | 0.080 (3) | 0.071 (2) | 0.086 (3) | −0.0072 (17) | −0.0249 (18) | 0.0174 (16) |
| C(10) | 0.091 (3) | 0.083 (2) | 0.0624 (17) | −0.0093 (19) | −0.0075 (17) | −0.0003 (15) |
| C(11) | 0.0663 (19) | 0.0701 (17) | 0.0639 (17) | 0.0031 (14) | 0.0038 (14) | −0.0034 (13) |
| C(12) | 0.0423 (15) | 0.0572 (14) | 0.0580 (15) | −0.0024 (12) | 0.0021 (12) | 0.0057 (11) |
| C(13) | 0.0521 (17) | 0.0688 (17) | 0.0670 (16) | 0.0033 (14) | 0.0018 (14) | 0.0059 (13) |
| C(14) | 0.077 (3) | 0.0753 (19) | 0.0592 (16) | 0.0003 (16) | −0.0070 (15) | 0.0029 (14) |
| C(15) | 0.081 (3) | 0.0638 (17) | 0.0604 (16) | −0.0040 (16) | 0.0129 (16) | 0.0014 (13) |
| C(16) | 0.0560 (18) | 0.0653 (17) | 0.089 (2) | 0.0075 (14) | 0.0120 (16) | −0.0044 (15) |
| C(17) | 0.0489 (17) | 0.0655 (16) | 0.0741 (17) | 0.0055 (13) | −0.0023 (13) | −0.0065 (13) |
| C(18) | 0.0468 (16) | 0.0497 (14) | 0.0682 (16) | 0.0050 (12) | 0.0050 (13) | 0.0004 (12) |
| C(19) | 0.0449 (16) | 0.0562 (14) | 0.0567 (14) | −0.0011 (12) | 0.0094 (12) | −0.0019 (11) |
| C(20) | 0.0558 (18) | 0.090 (2) | 0.0554 (16) | 0.0107 (16) | 0.0102 (14) | 0.0036 (14) |
| C(21) | 0.073 (2) | 0.132 (3) | 0.0592 (17) | 0.015 (2) | 0.0067 (15) | 0.0116 (17) |
| C(22) | 0.093 (3) | 0.146 (4) | 0.0635 (19) | 0.006 (3) | 0.0223 (19) | −0.0039 (18) |
| C(23) | 0.069 (2) | 0.107 (3) | 0.0762 (19) | 0.0100 (18) | 0.0269 (17) | −0.0053 (17) |
| Cl(1)—C(15) | 1.745 (3) | C(20)—C(21) | 1.497 (4) |
| O(1)—C(2) | 1.418 (3) | C(21)—C(22) | 1.485 (5) |
| O(1)—C(5) | 1.434 (3) | C(22)—C(23) | 1.505 (4) |
| O(2)—C(18) | 1.221 (3) | C(2)—H(2) | 0.980 |
| C(2)—C(3) | 1.573 (4) | C(3)—H(3) | 0.980 |
| C(2)—C(12) | 1.509 (4) | C(4)—H(4A) | 0.970 |
| C(3)—C(4) | 1.526 (4) | C(4)—H(4B) | 0.970 |
| C(3)—C(18) | 1.511 (4) | C(5)—H(5) | 0.980 |
| C(4)—C(5) | 1.521 (4) | C(7)—H(7) | 0.930 |
| C(5)—C(6) | 1.491 (4) | C(8)—H(8) | 0.930 |
| C(6)—C(7) | 1.376 (4) | C(9)—H(9) | 0.930 |
| C(6)—C(11) | 1.381 (4) | C(10)—H(10) | 0.930 |
| C(7)—C(8) | 1.382 (4) | C(11)—H(11) | 0.930 |
| C(8)—C(9) | 1.366 (5) | C(13)—H(13) | 0.930 |
| C(9)—C(10) | 1.363 (5) | C(14)—H(14) | 0.930 |
| C(10)—C(11) | 1.382 (4) | C(16)—H(16) | 0.930 |
| C(12)—C(13) | 1.382 (4) | C(17)—H(17) | 0.930 |
| C(12)—C(17) | 1.386 (4) | C(20)—H(20) | 0.96 (3) |
| C(13)—C(14) | 1.379 (4) | C(21)—H(21A) | 0.970 |
| C(14)—C(15) | 1.370 (5) | C(21)—H(21B) | 0.970 |
| C(15)—C(16) | 1.375 (4) | C(22)—H(22A) | 0.970 |
| C(16)—C(17) | 1.380 (4) | C(22)—H(22B) | 0.970 |
| C(18)—C(19) | 1.467 (4) | C(23)—H(23A) | 0.970 |
| C(19)—C(20) | 1.318 (4) | C(23)—H(23B) | 0.970 |
| C(19)—C(23) | 1.488 (4) | ||
| O(2)···C(2)i | 3.460 (3) | H(8)···H(4A)iv | 3.5198 |
| O(2)···C(8)ii | 3.575 (4) | H(8)···H(4B)iv | 3.3875 |
| O(2)···C(13)i | 3.537 (4) | H(8)···H(5)i | 2.7276 |
| C(2)···O(2)iii | 3.460 (3) | H(8)···H(11)i | 3.0564 |
| C(8)···O(2)iv | 3.575 (4) | H(8)···H(23B)iv | 3.5412 |
| C(8)···C(18)iv | 3.475 (4) | H(8)···H(20)iv | 3.2315 |
| C(8)···C(19)iv | 3.572 (4) | H(9)···Cl(1)ii | 3.4433 |
| C(11)···C(15)v | 3.582 (4) | H(9)···Cl(1)x | 3.5629 |
| C(13)···O(2)iii | 3.537 (4) | H(9)···C(19)iv | 3.4151 |
| C(15)···C(11)vi | 3.582 (4) | H(9)···C(20)iv | 3.4699 |
| C(18)···C(8)ii | 3.475 (4) | H(9)···C(21)iv | 3.5022 |
| C(19)···C(8)ii | 3.572 (4) | H(9)···C(22)iv | 3.5828 |
| Cl(1)···H(9)iv | 3.4433 | H(9)···C(23)iv | 3.4077 |
| Cl(1)···H(9)vii | 3.5629 | H(9)···H(11)i | 3.1235 |
| Cl(1)···H(10)vi | 3.4222 | H(9)···H(16)ii | 3.4677 |
| Cl(1)···H(10)vii | 3.3528 | H(9)···H(21B)iv | 3.0383 |
| Cl(1)···H(11)vi | 3.3964 | H(9)···H(22A)iv | 3.3010 |
| Cl(1)···H(21B)viii | 3.5133 | H(9)···H(23B)iv | 2.8899 |
| Cl(1)···H(22A)ix | 3.1389 | H(10)···Cl(1)v | 3.4222 |
| O(1)···H(4B)vi | 2.7496 | H(10)···Cl(1)x | 3.3528 |
| O(1)···H(7)iii | 3.4997 | H(10)···C(15)v | 3.5757 |
| O(1)···H(8)iii | 3.3806 | H(10)···H(14)v | 3.4412 |
| O(2)···H(2)i | 2.6806 | H(10)···H(16)ii | 3.0881 |
| O(2)···H(3)i | 3.0662 | H(10)···H(21B)vi | 2.8666 |
| O(2)···H(8)ii | 3.2230 | H(11)···Cl(1)v | 3.3964 |
| O(2)···H(13)i | 2.6883 | H(11)···C(8)iii | 3.2748 |
| O(2)···H(20)i | 3.03 (3) | H(11)···C(9)iii | 3.3137 |
| C(2)···H(4B)vi | 3.3645 | H(11)···C(14)v | 3.2922 |
| C(3)···H(8)ii | 3.3504 | H(11)···C(15)v | 2.8298 |
| C(5)···H(8)iii | 3.2463 | H(11)···C(16)v | 2.8939 |
| C(6)···H(8)iii | 3.3292 | H(11)···C(17)v | 3.4096 |
| C(6)···H(20)vi | 3.52 (3) | H(11)···H(8)iii | 3.0564 |
| C(7)···H(2)i | 3.5722 | H(11)···H(9)iii | 3.1235 |
| C(7)···H(5)i | 3.1280 | H(11)···H(16)v | 3.1385 |
| C(7)···H(20)vi | 3.44 (3) | H(13)···O(2)iii | 2.6883 |
| C(8)···H(5)i | 2.9455 | H(13)···C(16)iii | 3.2505 |
| C(8)···H(11)i | 3.2748 | H(13)···C(17)iii | 3.2991 |
| C(8)···H(20)vi | 3.29 (3) | H(13)···H(16)iii | 3.0320 |
| C(9)···H(11)i | 3.3137 | H(13)···H(17)iii | 3.1180 |
| C(9)···H(16)ii | 3.2006 | H(13)···H(23A)iii | 3.0864 |
| C(9)···H(23B)iv | 3.2533 | H(13)···H(23B)iii | 3.5534 |
| C(9)···H(20)vi | 3.20 (3) | H(14)···C(21)viii | 3.0892 |
| C(10)···H(16)ii | 2.9601 | H(14)···C(22)viii | 3.1317 |
| C(10)···H(21B)vi | 3.1472 | H(14)···H(10)vi | 3.4412 |
| C(10)···H(20)vi | 3.26 (3) | H(14)···H(16)iii | 3.0912 |
| C(11)···H(8)iii | 3.2826 | H(14)···H(21A)viii | 2.8734 |
| C(11)···H(16)ii | 3.3447 | H(14)···H(21B)viii | 2.8730 |
| C(11)···H(20)vi | 3.41 (3) | H(14)···H(22A)viii | 2.7927 |
| C(12)···H(4B)vi | 3.3030 | H(14)···H(22B)viii | 3.0585 |
| C(13)···H(16)iii | 3.2583 | H(16)···C(9)iv | 3.2006 |
| C(14)···H(11)vi | 3.2922 | H(16)···C(10)iv | 2.9601 |
| C(14)···H(16)iii | 3.2907 | H(16)···C(11)iv | 3.3447 |
| C(14)···H(21A)viii | 3.4806 | H(16)···C(13)i | 3.2583 |
| C(15)···H(10)vi | 3.5757 | H(16)···C(14)i | 3.2907 |
| C(15)···H(11)vi | 2.8298 | H(16)···H(9)iv | 3.4677 |
| C(15)···H(22A)ix | 3.5571 | H(16)···H(10)iv | 3.0881 |
| C(16)···H(11)vi | 2.8939 | H(16)···H(11)vi | 3.1385 |
| C(16)···H(13)i | 3.2505 | H(16)···H(13)i | 3.0320 |
| C(17)···H(4B)vi | 3.3692 | H(16)···H(14)i | 3.0912 |
| C(17)···H(11)vi | 3.4096 | H(17)···H(2)i | 3.2711 |
| C(17)···H(13)i | 3.2991 | H(17)···H(4B)vi | 3.2998 |
| C(18)···H(8)ii | 2.8538 | H(17)···H(13)i | 3.1180 |
| C(19)···H(8)ii | 2.9837 | H(21A)···C(14)viii | 3.4806 |
| C(19)···H(9)ii | 3.4151 | H(21A)···C(23)iii | 3.1440 |
| C(20)···H(8)ii | 3.2142 | H(21A)···H(14)viii | 2.8734 |
| C(20)···H(9)ii | 3.4699 | H(21A)···H(22A)iii | 3.3502 |
| C(20)···H(23B)iii | 3.1048 | H(21A)···H(22B)viii | 2.7457 |
| C(21)···H(9)ii | 3.5022 | H(21A)···H(23A)iii | 3.2912 |
| C(21)···H(14)viii | 3.0892 | H(21A)···H(23B)iii | 2.3173 |
| C(21)···H(22B)viii | 3.5726 | H(21B)···Cl(1)viii | 3.5133 |
| C(21)···H(23B)iii | 3.0209 | H(21B)···C(10)v | 3.1472 |
| C(22)···H(9)ii | 3.5828 | H(21B)···H(9)ii | 3.0383 |
| C(22)···H(14)viii | 3.1317 | H(21B)···H(10)v | 2.8666 |
| C(22)···H(22B)ix | 3.4041 | H(21B)···H(14)viii | 2.8730 |
| C(22)···H(23A)ix | 3.1476 | H(21B)···H(23B)iii | 3.4145 |
| C(23)···H(9)ii | 3.4077 | H(22A)···Cl(1)ix | 3.1389 |
| C(23)···H(21A)i | 3.1440 | H(22A)···C(15)ix | 3.5571 |
| C(23)···H(22B)ix | 3.1328 | H(22A)···H(9)ii | 3.3010 |
| H(2)···O(2)iii | 2.6806 | H(22A)···H(14)viii | 2.7927 |
| H(2)···C(7)iii | 3.5722 | H(22A)···H(21A)i | 3.3502 |
| H(2)···H(4A)iii | 3.2970 | H(22A)···H(22B)ix | 3.3354 |
| H(2)···H(4B)vi | 3.4065 | H(22A)···H(23A)ix | 2.8646 |
| H(2)···H(7)iii | 2.8478 | H(22B)···C(21)viii | 3.5726 |
| H(2)···H(17)iii | 3.2711 | H(22B)···C(22)ix | 3.4041 |
| H(3)···O(2)iii | 3.0662 | H(22B)···C(23)ix | 3.1328 |
| H(3)···H(8)ii | 3.1877 | H(22B)···H(14)viii | 3.0585 |
| H(4A)···H(2)i | 3.2970 | H(22B)···H(21A)viii | 2.7457 |
| H(4A)···H(7)ii | 3.4183 | H(22B)···H(22A)ix | 3.3354 |
| H(4A)···H(8)ii | 3.5198 | H(22B)···H(22B)viii | 3.0914 |
| H(4B)···O(1)v | 2.7496 | H(22B)···H(22B)ix | 3.1672 |
| H(4B)···C(2)v | 3.3645 | H(22B)···H(23A)ix | 2.6197 |
| H(4B)···C(12)v | 3.3030 | H(22B)···H(23B)ix | 3.0847 |
| H(4B)···C(17)v | 3.3692 | H(23A)···C(22)ix | 3.1476 |
| H(4B)···H(2)v | 3.4065 | H(23A)···H(13)i | 3.0864 |
| H(4B)···H(7)ii | 3.4863 | H(23A)···H(21A)i | 3.2912 |
| H(4B)···H(8)ii | 3.3875 | H(23A)···H(22A)ix | 2.8646 |
| H(4B)···H(17)v | 3.2998 | H(23A)···H(22B)ix | 2.6197 |
| H(5)···C(7)iii | 3.1280 | H(23B)···C(9)ii | 3.2533 |
| H(5)···C(8)iii | 2.9455 | H(23B)···C(20)i | 3.1048 |
| H(5)···H(7)iii | 3.0467 | H(23B)···C(21)i | 3.0209 |
| H(5)···H(8)iii | 2.7276 | H(23B)···H(8)ii | 3.5412 |
| H(7)···O(1)i | 3.4997 | H(23B)···H(9)ii | 2.8899 |
| H(7)···H(2)i | 2.8478 | H(23B)···H(13)i | 3.5534 |
| H(7)···H(4A)iv | 3.4183 | H(23B)···H(21A)i | 2.3173 |
| H(7)···H(4B)iv | 3.4863 | H(23B)···H(21B)i | 3.4145 |
| H(7)···H(5)i | 3.0467 | H(23B)···H(22B)ix | 3.0847 |
| H(8)···O(1)i | 3.3806 | H(23B)···H(20)i | 2.8072 |
| H(8)···O(2)iv | 3.2230 | H(20)···O(2)iii | 3.03 (3) |
| H(8)···C(3)iv | 3.3504 | H(20)···C(6)v | 3.52 (3) |
| H(8)···C(5)i | 3.2463 | H(20)···C(7)v | 3.44 (3) |
| H(8)···C(6)i | 3.3292 | H(20)···C(8)v | 3.29 (3) |
| H(8)···C(11)i | 3.2826 | H(20)···C(9)v | 3.20 (3) |
| H(8)···C(18)iv | 2.8538 | H(20)···C(10)v | 3.26 (3) |
| H(8)···C(19)iv | 2.9837 | H(20)···C(11)v | 3.41 (3) |
| H(8)···C(20)iv | 3.2142 | H(20)···H(8)ii | 3.2315 |
| H(8)···H(3)iv | 3.1877 | H(20)···H(23B)iii | 2.8072 |
| C(2)—O(1)—C(5) | 107.08 (17) | C(18)—C(3)—H(3) | 109.756 |
| O(1)—C(2)—C(3) | 105.33 (18) | C(3)—C(4)—H(4A) | 110.822 |
| O(1)—C(2)—C(12) | 109.62 (19) | C(3)—C(4)—H(4B) | 110.830 |
| C(3)—C(2)—C(12) | 116.0 (2) | C(5)—C(4)—H(4A) | 110.820 |
| C(2)—C(3)—C(4) | 103.30 (19) | C(5)—C(4)—H(4B) | 110.820 |
| C(2)—C(3)—C(18) | 110.98 (19) | H(4A)—C(4)—H(4B) | 108.881 |
| C(4)—C(3)—C(18) | 113.2 (2) | O(1)—C(5)—H(5) | 109.307 |
| C(3)—C(4)—C(5) | 104.6 (2) | C(4)—C(5)—H(5) | 109.305 |
| O(1)—C(5)—C(4) | 103.60 (18) | C(6)—C(5)—H(5) | 109.316 |
| O(1)—C(5)—C(6) | 110.1 (2) | C(6)—C(7)—H(7) | 119.692 |
| C(4)—C(5)—C(6) | 115.0 (2) | C(8)—C(7)—H(7) | 119.701 |
| C(5)—C(6)—C(7) | 121.2 (3) | C(7)—C(8)—H(8) | 119.783 |
| C(5)—C(6)—C(11) | 120.5 (3) | C(9)—C(8)—H(8) | 119.795 |
| C(7)—C(6)—C(11) | 118.2 (3) | C(8)—C(9)—H(9) | 120.091 |
| C(6)—C(7)—C(8) | 120.6 (3) | C(10)—C(9)—H(9) | 120.106 |
| C(7)—C(8)—C(9) | 120.4 (3) | C(9)—C(10)—H(10) | 120.016 |
| C(8)—C(9)—C(10) | 119.8 (3) | C(11)—C(10)—H(10) | 120.013 |
| C(9)—C(10)—C(11) | 120.0 (3) | C(6)—C(11)—H(11) | 119.505 |
| C(6)—C(11)—C(10) | 121.0 (3) | C(10)—C(11)—H(11) | 119.501 |
| C(2)—C(12)—C(13) | 119.8 (3) | C(12)—C(13)—H(13) | 119.632 |
| C(2)—C(12)—C(17) | 121.6 (2) | C(14)—C(13)—H(13) | 119.645 |
| C(13)—C(12)—C(17) | 118.5 (3) | C(13)—C(14)—H(14) | 120.183 |
| C(12)—C(13)—C(14) | 120.7 (3) | C(15)—C(14)—H(14) | 120.201 |
| C(13)—C(14)—C(15) | 119.6 (3) | C(15)—C(16)—H(16) | 120.539 |
| Cl(1)—C(15)—C(14) | 119.9 (2) | C(17)—C(16)—H(16) | 120.562 |
| Cl(1)—C(15)—C(16) | 119.0 (3) | C(12)—C(17)—H(17) | 119.414 |
| C(14)—C(15)—C(16) | 121.1 (3) | C(16)—C(17)—H(17) | 119.421 |
| C(15)—C(16)—C(17) | 118.9 (3) | C(19)—C(20)—H(20) | 124.5 (15) |
| C(12)—C(17)—C(16) | 121.2 (3) | C(21)—C(20)—H(20) | 123.6 (15) |
| O(2)—C(18)—C(3) | 121.0 (2) | C(20)—C(21)—H(21A) | 110.941 |
| O(2)—C(18)—C(19) | 119.8 (3) | C(20)—C(21)—H(21B) | 110.944 |
| C(3)—C(18)—C(19) | 119.2 (3) | C(22)—C(21)—H(21A) | 110.955 |
| C(18)—C(19)—C(20) | 127.7 (3) | C(22)—C(21)—H(21B) | 110.945 |
| C(18)—C(19)—C(23) | 120.9 (3) | H(21A)—C(21)—H(21B) | 108.957 |
| C(20)—C(19)—C(23) | 111.3 (3) | C(21)—C(22)—H(22A) | 110.164 |
| C(19)—C(20)—C(21) | 111.8 (3) | C(21)—C(22)—H(22B) | 110.161 |
| C(20)—C(21)—C(22) | 104.1 (3) | C(23)—C(22)—H(22A) | 110.158 |
| C(21)—C(22)—C(23) | 107.7 (3) | C(23)—C(22)—H(22B) | 110.167 |
| C(19)—C(23)—C(22) | 104.2 (3) | H(22A)—C(22)—H(22B) | 108.463 |
| O(1)—C(2)—H(2) | 108.562 | C(19)—C(23)—H(23A) | 110.912 |
| C(3)—C(2)—H(2) | 108.556 | C(19)—C(23)—H(23B) | 110.920 |
| C(12)—C(2)—H(2) | 108.535 | C(22)—C(23)—H(23A) | 110.929 |
| C(2)—C(3)—H(3) | 109.737 | C(22)—C(23)—H(23B) | 110.927 |
| C(4)—C(3)—H(3) | 109.735 | H(23A)—C(23)—H(23B) | 108.947 |
| C(2)—O(1)—C(5)—C(4) | −41.7 (2) | C(11)—C(6)—C(7)—C(8) | −0.6 (4) |
| C(2)—O(1)—C(5)—C(6) | −165.24 (17) | C(6)—C(7)—C(8)—C(9) | −0.0 (4) |
| C(5)—O(1)—C(2)—C(3) | 34.0 (2) | C(7)—C(8)—C(9)—C(10) | 0.4 (5) |
| C(5)—O(1)—C(2)—C(12) | 159.47 (17) | C(8)—C(9)—C(10)—C(11) | −0.1 (5) |
| O(1)—C(2)—C(3)—C(4) | −12.5 (3) | C(9)—C(10)—C(11)—C(6) | −0.6 (5) |
| O(1)—C(2)—C(3)—C(18) | 109.02 (18) | C(2)—C(12)—C(13)—C(14) | 175.9 (2) |
| O(1)—C(2)—C(12)—C(13) | 151.51 (18) | C(2)—C(12)—C(17)—C(16) | −175.4 (2) |
| O(1)—C(2)—C(12)—C(17) | −31.7 (3) | C(13)—C(12)—C(17)—C(16) | 1.4 (4) |
| C(3)—C(2)—C(12)—C(13) | −89.4 (3) | C(17)—C(12)—C(13)—C(14) | −1.0 (4) |
| C(3)—C(2)—C(12)—C(17) | 87.4 (3) | C(12)—C(13)—C(14)—C(15) | −0.2 (4) |
| C(12)—C(2)—C(3)—C(4) | −133.95 (19) | C(13)—C(14)—C(15)—Cl(1) | 179.5 (2) |
| C(12)—C(2)—C(3)—C(18) | −12.4 (3) | C(13)—C(14)—C(15)—C(16) | 1.1 (4) |
| C(2)—C(3)—C(4)—C(5) | −11.7 (3) | Cl(1)—C(15)—C(16)—C(17) | −179.07 (17) |
| C(2)—C(3)—C(18)—O(2) | −85.7 (3) | C(14)—C(15)—C(16)—C(17) | −0.6 (4) |
| C(2)—C(3)—C(18)—C(19) | 91.9 (3) | C(15)—C(16)—C(17)—C(12) | −0.6 (4) |
| C(4)—C(3)—C(18)—O(2) | 29.9 (3) | O(2)—C(18)—C(19)—C(20) | −162.7 (2) |
| C(4)—C(3)—C(18)—C(19) | −152.55 (18) | O(2)—C(18)—C(19)—C(23) | 13.7 (4) |
| C(18)—C(3)—C(4)—C(5) | −131.75 (19) | C(3)—C(18)—C(19)—C(20) | 19.7 (4) |
| C(3)—C(4)—C(5)—O(1) | 31.9 (3) | C(3)—C(18)—C(19)—C(23) | −163.86 (18) |
| C(3)—C(4)—C(5)—C(6) | 152.05 (19) | C(18)—C(19)—C(20)—C(21) | 176.2 (2) |
| O(1)—C(5)—C(6)—C(7) | 42.3 (3) | C(18)—C(19)—C(23)—C(22) | 177.59 (19) |
| O(1)—C(5)—C(6)—C(11) | −140.95 (19) | C(20)—C(19)—C(23)—C(22) | −5.5 (3) |
| C(4)—C(5)—C(6)—C(7) | −74.2 (3) | C(23)—C(19)—C(20)—C(21) | −0.5 (3) |
| C(4)—C(5)—C(6)—C(11) | 102.5 (3) | C(19)—C(20)—C(21)—C(22) | 6.3 (4) |
| C(5)—C(6)—C(7)—C(8) | 176.2 (2) | C(20)—C(21)—C(22)—C(23) | −9.4 (4) |
| C(5)—C(6)—C(11)—C(10) | −175.9 (2) | C(21)—C(22)—C(23)—C(19) | 9.2 (4) |
| C(7)—C(6)—C(11)—C(10) | 0.9 (4) |
| Symmetry codes: (i) x+1, y, z; (ii) −x+3/2, y+1/2, −z+3/2; (iii) x−1, y, z; (iv) −x+3/2, y−1/2, −z+3/2; (v) −x+1/2, y+1/2, −z+3/2; (vi) −x+1/2, y−1/2, −z+3/2; (vii) x−1/2, −y+1/2, z−1/2; (viii) −x, −y+1, −z+1; (ix) −x+1, −y+1, −z+1; (x) x+1/2, −y+1/2, z+1/2. |
Fiancial support from the Korea Institute of Science and Technology (KIST) is gratefully acknowledged.
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The oxolane moiety is an important heterocycle constituent in many bioactive natural products. New synthetic methodologies for 2,5-disubstituted oxolanes having an allenyl group, via Prins-type cyclization, has been subject of development since last decade (Shin et al., 2005). Cohen and colleagues synthesized the polysubstituted oxolane by Prins-Pinacol reaction (Cohen et al., 2001). 5-Exocyclic products, 2,3,5-trisustituted oxolanes, were synthesized from homopropargylic alcohols with alkynes and aldehydes (Chavre et al., 2006, 2008).
In the molecule of Fig. 1, the oxolane ring adopts a twisted conformation on C5–O1. The dihedral angle between the chlorophenyl and cyclopentenyl rings is 31.03 (17)°.