supplementary materials


go2037 scheme

Acta Cryst. (2012). E68, o45    [ doi:10.1107/S1600536811051993 ]

[2-(4-Chlorophenyl)-5-phenyloxolan-3-yl](cyclopentenyl)methanone

J. K. Lee, S. N. Chavre, Y. S. Cho, Y. Lee and J. H. Cha

Abstract top

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.

Comment top

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)°.

Related literature top

For general background to the Prins-type cyclization for the synthesis of oxolanes, see: Chavre et al. (2006, 2008); Cohen et al. (2001); Shin et al. (2005).

Experimental top

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.

Refinement top

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.

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The structure of the title compound, with displacement ellipsoids drawn at the 50% probability level and H atoms with arbitrary radius.
[2-(4-Chlorophenyl)-5-phenyloxolan-3-yl](cyclopentenyl)methanone top
Crystal data top
C22H21ClO2F(000) = 744.00
Mr = 352.86Dx = 1.259 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2ynCell parameters from 12997 reflections
a = 5.7575 (6) Åθ = 3.1–68.3°
b = 11.3547 (12) ŵ = 1.90 mm1
c = 28.554 (3) ÅT = 296 K
β = 94.442 (8)°Needle, yellow
V = 1861.1 (4) Å30.50 × 0.20 × 0.20 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2012 reflections with F2 > 2σ(F2)
Detector resolution: 10.000 pixels mm-1Rint = 0.073
ω scansθmax = 68.2°
Absorption correction: multi-scan
(ABSCOR; Rigaku, 1995)
h = 66
Tmin = 0.301, Tmax = 0.684k = 1313
18544 measured reflectionsl = 3434
3363 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H 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 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.19 e Å3
Primary atom site location: structure-invariant direct methods
Crystal data top
C22H21ClO2V = 1861.1 (4) Å3
Mr = 352.86Z = 4
Monoclinic, P21/nCu Kα radiation
a = 5.7575 (6) ŵ = 1.90 mm1
b = 11.3547 (12) ÅT = 296 K
c = 28.554 (3) Å0.50 × 0.20 × 0.20 mm
β = 94.442 (8)°
Data collection top
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 = 0.684Rint = 0.073
18544 measured reflectionsθmax = 68.2°
Refinement top
R[F2 > 2σ(F2)] = 0.051H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.139Δρmax = 0.20 e Å3
S = 1.05Δρmin = 0.19 e Å3
3363 reflectionsAbsolute structure: ?
230 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/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)0.01710.42400.70430.0689*
H(3)0.15050.60410.69120.0673*
H(4A)0.57460.57020.74260.0840*
H(4B)0.36120.64510.75730.0840*
H(5)0.18390.48770.78720.0723*
H(7)0.72950.34950.77550.0818*
H(8)1.00390.30770.83630.0963*
H(9)0.94780.36730.91130.0966*
H(10)0.61510.46740.92620.0954*
H(11)0.33800.50830.86570.0802*
H(13)0.08270.37650.62270.0753*
H(14)0.02110.26350.55770.0855*
H(16)0.59870.16360.61740.0836*
H(17)0.53450.27490.68280.0758*
H(21A)0.04190.64440.53420.1057*
H(21B)0.10900.75980.54230.1057*
H(22A)0.38330.67100.50780.1199*
H(22B)0.24950.55010.50810.1199*
H(23A)0.50630.49180.56380.0994*
H(23B)0.61200.61980.56940.0994*
H(20)0.033 (5)0.672 (3)0.6215 (9)0.086 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
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)
Geometric parameters (Å, °) top
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)i3.460 (3)H(8)···H(4A)iv3.5198
O(2)···C(8)ii3.575 (4)H(8)···H(4B)iv3.3875
O(2)···C(13)i3.537 (4)H(8)···H(5)i2.7276
C(2)···O(2)iii3.460 (3)H(8)···H(11)i3.0564
C(8)···O(2)iv3.575 (4)H(8)···H(23B)iv3.5412
C(8)···C(18)iv3.475 (4)H(8)···H(20)iv3.2315
C(8)···C(19)iv3.572 (4)H(9)···Cl(1)ii3.4433
C(11)···C(15)v3.582 (4)H(9)···Cl(1)x3.5629
C(13)···O(2)iii3.537 (4)H(9)···C(19)iv3.4151
C(15)···C(11)vi3.582 (4)H(9)···C(20)iv3.4699
C(18)···C(8)ii3.475 (4)H(9)···C(21)iv3.5022
C(19)···C(8)ii3.572 (4)H(9)···C(22)iv3.5828
Cl(1)···H(9)iv3.4433H(9)···C(23)iv3.4077
Cl(1)···H(9)vii3.5629H(9)···H(11)i3.1235
Cl(1)···H(10)vi3.4222H(9)···H(16)ii3.4677
Cl(1)···H(10)vii3.3528H(9)···H(21B)iv3.0383
Cl(1)···H(11)vi3.3964H(9)···H(22A)iv3.3010
Cl(1)···H(21B)viii3.5133H(9)···H(23B)iv2.8899
Cl(1)···H(22A)ix3.1389H(10)···Cl(1)v3.4222
O(1)···H(4B)vi2.7496H(10)···Cl(1)x3.3528
O(1)···H(7)iii3.4997H(10)···C(15)v3.5757
O(1)···H(8)iii3.3806H(10)···H(14)v3.4412
O(2)···H(2)i2.6806H(10)···H(16)ii3.0881
O(2)···H(3)i3.0662H(10)···H(21B)vi2.8666
O(2)···H(8)ii3.2230H(11)···Cl(1)v3.3964
O(2)···H(13)i2.6883H(11)···C(8)iii3.2748
O(2)···H(20)i3.03 (3)H(11)···C(9)iii3.3137
C(2)···H(4B)vi3.3645H(11)···C(14)v3.2922
C(3)···H(8)ii3.3504H(11)···C(15)v2.8298
C(5)···H(8)iii3.2463H(11)···C(16)v2.8939
C(6)···H(8)iii3.3292H(11)···C(17)v3.4096
C(6)···H(20)vi3.52 (3)H(11)···H(8)iii3.0564
C(7)···H(2)i3.5722H(11)···H(9)iii3.1235
C(7)···H(5)i3.1280H(11)···H(16)v3.1385
C(7)···H(20)vi3.44 (3)H(13)···O(2)iii2.6883
C(8)···H(5)i2.9455H(13)···C(16)iii3.2505
C(8)···H(11)i3.2748H(13)···C(17)iii3.2991
C(8)···H(20)vi3.29 (3)H(13)···H(16)iii3.0320
C(9)···H(11)i3.3137H(13)···H(17)iii3.1180
C(9)···H(16)ii3.2006H(13)···H(23A)iii3.0864
C(9)···H(23B)iv3.2533H(13)···H(23B)iii3.5534
C(9)···H(20)vi3.20 (3)H(14)···C(21)viii3.0892
C(10)···H(16)ii2.9601H(14)···C(22)viii3.1317
C(10)···H(21B)vi3.1472H(14)···H(10)vi3.4412
C(10)···H(20)vi3.26 (3)H(14)···H(16)iii3.0912
C(11)···H(8)iii3.2826H(14)···H(21A)viii2.8734
C(11)···H(16)ii3.3447H(14)···H(21B)viii2.8730
C(11)···H(20)vi3.41 (3)H(14)···H(22A)viii2.7927
C(12)···H(4B)vi3.3030H(14)···H(22B)viii3.0585
C(13)···H(16)iii3.2583H(16)···C(9)iv3.2006
C(14)···H(11)vi3.2922H(16)···C(10)iv2.9601
C(14)···H(16)iii3.2907H(16)···C(11)iv3.3447
C(14)···H(21A)viii3.4806H(16)···C(13)i3.2583
C(15)···H(10)vi3.5757H(16)···C(14)i3.2907
C(15)···H(11)vi2.8298H(16)···H(9)iv3.4677
C(15)···H(22A)ix3.5571H(16)···H(10)iv3.0881
C(16)···H(11)vi2.8939H(16)···H(11)vi3.1385
C(16)···H(13)i3.2505H(16)···H(13)i3.0320
C(17)···H(4B)vi3.3692H(16)···H(14)i3.0912
C(17)···H(11)vi3.4096H(17)···H(2)i3.2711
C(17)···H(13)i3.2991H(17)···H(4B)vi3.2998
C(18)···H(8)ii2.8538H(17)···H(13)i3.1180
C(19)···H(8)ii2.9837H(21A)···C(14)viii3.4806
C(19)···H(9)ii3.4151H(21A)···C(23)iii3.1440
C(20)···H(8)ii3.2142H(21A)···H(14)viii2.8734
C(20)···H(9)ii3.4699H(21A)···H(22A)iii3.3502
C(20)···H(23B)iii3.1048H(21A)···H(22B)viii2.7457
C(21)···H(9)ii3.5022H(21A)···H(23A)iii3.2912
C(21)···H(14)viii3.0892H(21A)···H(23B)iii2.3173
C(21)···H(22B)viii3.5726H(21B)···Cl(1)viii3.5133
C(21)···H(23B)iii3.0209H(21B)···C(10)v3.1472
C(22)···H(9)ii3.5828H(21B)···H(9)ii3.0383
C(22)···H(14)viii3.1317H(21B)···H(10)v2.8666
C(22)···H(22B)ix3.4041H(21B)···H(14)viii2.8730
C(22)···H(23A)ix3.1476H(21B)···H(23B)iii3.4145
C(23)···H(9)ii3.4077H(22A)···Cl(1)ix3.1389
C(23)···H(21A)i3.1440H(22A)···C(15)ix3.5571
C(23)···H(22B)ix3.1328H(22A)···H(9)ii3.3010
H(2)···O(2)iii2.6806H(22A)···H(14)viii2.7927
H(2)···C(7)iii3.5722H(22A)···H(21A)i3.3502
H(2)···H(4A)iii3.2970H(22A)···H(22B)ix3.3354
H(2)···H(4B)vi3.4065H(22A)···H(23A)ix2.8646
H(2)···H(7)iii2.8478H(22B)···C(21)viii3.5726
H(2)···H(17)iii3.2711H(22B)···C(22)ix3.4041
H(3)···O(2)iii3.0662H(22B)···C(23)ix3.1328
H(3)···H(8)ii3.1877H(22B)···H(14)viii3.0585
H(4A)···H(2)i3.2970H(22B)···H(21A)viii2.7457
H(4A)···H(7)ii3.4183H(22B)···H(22A)ix3.3354
H(4A)···H(8)ii3.5198H(22B)···H(22B)viii3.0914
H(4B)···O(1)v2.7496H(22B)···H(22B)ix3.1672
H(4B)···C(2)v3.3645H(22B)···H(23A)ix2.6197
H(4B)···C(12)v3.3030H(22B)···H(23B)ix3.0847
H(4B)···C(17)v3.3692H(23A)···C(22)ix3.1476
H(4B)···H(2)v3.4065H(23A)···H(13)i3.0864
H(4B)···H(7)ii3.4863H(23A)···H(21A)i3.2912
H(4B)···H(8)ii3.3875H(23A)···H(22A)ix2.8646
H(4B)···H(17)v3.2998H(23A)···H(22B)ix2.6197
H(5)···C(7)iii3.1280H(23B)···C(9)ii3.2533
H(5)···C(8)iii2.9455H(23B)···C(20)i3.1048
H(5)···H(7)iii3.0467H(23B)···C(21)i3.0209
H(5)···H(8)iii2.7276H(23B)···H(8)ii3.5412
H(7)···O(1)i3.4997H(23B)···H(9)ii2.8899
H(7)···H(2)i2.8478H(23B)···H(13)i3.5534
H(7)···H(4A)iv3.4183H(23B)···H(21A)i2.3173
H(7)···H(4B)iv3.4863H(23B)···H(21B)i3.4145
H(7)···H(5)i3.0467H(23B)···H(22B)ix3.0847
H(8)···O(1)i3.3806H(23B)···H(20)i2.8072
H(8)···O(2)iv3.2230H(20)···O(2)iii3.03 (3)
H(8)···C(3)iv3.3504H(20)···C(6)v3.52 (3)
H(8)···C(5)i3.2463H(20)···C(7)v3.44 (3)
H(8)···C(6)i3.3292H(20)···C(8)v3.29 (3)
H(8)···C(11)i3.2826H(20)···C(9)v3.20 (3)
H(8)···C(18)iv2.8538H(20)···C(10)v3.26 (3)
H(8)···C(19)iv2.9837H(20)···C(11)v3.41 (3)
H(8)···C(20)iv3.2142H(20)···H(8)ii3.2315
H(8)···H(3)iv3.1877H(20)···H(23B)iii2.8072
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)108.562C(19)—C(23)—H(23A)110.912
C(3)—C(2)—H(2)108.556C(19)—C(23)—H(23B)110.920
C(12)—C(2)—H(2)108.535C(22)—C(23)—H(23A)110.929
C(2)—C(3)—H(3)109.737C(22)—C(23)—H(23B)110.927
C(4)—C(3)—H(3)109.735H(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.
Acknowledgements top

Fiancial support from the Korea Institute of Science and Technology (KIST) is gratefully acknowledged.

references
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