高等学校化学学报 ›› 2017, Vol. 38 ›› Issue (3): 403.doi: 10.7503/cjcu20160717
收稿日期:
2016-10-14
出版日期:
2017-03-10
发布日期:
2017-01-23
作者简介:
联系人简介: 王明安, 男, 博士, 教授, 博士生导师, 主要从事有机合成及新农药创制研究. E-mail: 基金资助:
YANG Mingyan, ZHANG Li, WANG Daoquan, WANG Ming an*()
Received:
2016-10-14
Online:
2017-03-10
Published:
2017-01-23
Contact:
WANG Ming an
E-mail:wangma@cau.edu.cn
Supported by:
摘要:
以环十二酮为原料, 经2-碘酰基苯甲酸(IBX)氧化制备2-环十二烯酮, 在醋酸钯和三苯基磷催化下, 2-环十二烯酮与苯硼酸反应制得3-苯基环十二酮. 经3-苯基环十二酮与不同试剂发生区域选择性反应制备了一系列新的3-苯基-12-取代环十二酮衍生物, 采用核磁共振波谱(NMR)和液相色谱-高分辨质谱(HRMS)表征了其结构. 在溶液中结晶, 获得了4个代表性化合物的单晶并进行X射线衍射分析, 结果表明, 3-苯基-12-取代环十二酮晶体中的十二元环仍采取[3333]-2-酮构象, 2个取代基为反式构型, 取代基存在2种情形: 2个取代基在同一条边上, 苯基位于与羰基间隔1个亚甲基的β-角碳反向位, 而另1个取代基位于与羰基另一侧相邻的α-角碳顺向位; 或2个取代基在2条边上, 苯基位于与羰基间隔1个亚甲基另一条边的β-边碳外向位, 而另1个取代基位于与羰基另一侧相邻并在同一条边的α-边碳外向位, 量子力学计算结果与晶体衍射分析结果一致.
中图分类号:
TrendMD:
杨明艳, 张莉, 王道全, 王明安. 反式-3-苯基-12-取代环十二酮的合成及晶体结构. 高等学校化学学报, 2017, 38(3): 403.
YANG Mingyan, ZHANG Li, WANG Daoquan, WANG Ming an. Synthesis and Crystal Structure of Trans-3-phenyl-12-substituted Cyclododecanone†. Chem. J. Chinese Universities, 2017, 38(3): 403.
Compd. | Appearance | m. p./℃ | Yield(%) | HRMS(ESI), m/z (cacld.) [M+H]+ |
---|---|---|---|---|
3a | White solid | 128—130 | 59 | 337.1162(337.1158) |
3b | White solid | 138—140 | 67 | 385.1024(385.1023) |
3c | White solid | 76—78 | 37 | 273.2210(273.2213) |
3d | White solid | 49—51 | 24 | 315.2679(315.2682) |
3e | White solid | 119—121 | 71 | 349.2517(349.2526) |
3f | White solid | 115—117 | 52 | 363.2310(363.2319) |
3g | White solid | 106—108 | 37 | 289.2157(289.2162) |
3h | White solid | 89—91 | 59 | 399.1988(399.1988) |
4 | White solid | 93—95 | 7 | 463.0528(463.0531) |
Table 1 Appearance, melting points, yields and HRMS data of compounds 3a—3f and 4
Compd. | Appearance | m. p./℃ | Yield(%) | HRMS(ESI), m/z (cacld.) [M+H]+ |
---|---|---|---|---|
3a | White solid | 128—130 | 59 | 337.1162(337.1158) |
3b | White solid | 138—140 | 67 | 385.1024(385.1023) |
3c | White solid | 76—78 | 37 | 273.2210(273.2213) |
3d | White solid | 49—51 | 24 | 315.2679(315.2682) |
3e | White solid | 119—121 | 71 | 349.2517(349.2526) |
3f | White solid | 115—117 | 52 | 363.2310(363.2319) |
3g | White solid | 106—108 | 37 | 289.2157(289.2162) |
3h | White solid | 89—91 | 59 | 399.1988(399.1988) |
4 | White solid | 93—95 | 7 | 463.0528(463.0531) |
Compd. | 1H NMR(300 MHz, CDCl3), δ | 13C NMR(75 MHz, CDCl3), δ |
---|---|---|
3a | 7.38—7.20(m, 5H), 4.59(dd, 1H,J=12.2, 3.6 Hz), 3.34—3.26(m, 1H), 3.08(dd, 1H, J=14.4, 3.1 Hz), 2.94(dd, 1H, J=12.2, 14.4 Hz), 2.51—2.42(m, 1H), 2.00—1.93(m, 1H), 1.63—1.08(m, 14H) | 203.8, 143.8, 128.5, 127.4, 126.5, 48.9, 43.9, 39.1, 33.1, 30.9, 24.7, 24.4, 24.2, 23.6, 22.3, 21.9 |
3b | 7.35—7.19(m, 5H), 4.99(dd, 1H, J=11.3, 3.6 Hz), 3.31(dd, 1H, J=13.5, 2.9 Hz), 3.17—3.12(m, 1H), 2.70—2.59(m, 2H), 2.01—1.92(m, 1H), 1.60—1.12(m, 14H) | 204.4, 143.7, 128.6, 127.4, 126.6, 45.9, 40.3, 34.9, 30.8, 25.9, 25.84, 25.81, 23.6, 23.0, 22.8, 22.2 |
3c | 7.30—7.18(m, 5H), 3.61—3.55(m, 1H), 3.33(dd, J=12.7, 8.5 Hz, 1H), 2.86—2.82(m, 1H), 2.37(dd, J=12.7, 2.2 Hz, 1H), 1.81—1.07(m, 16H), 1.06(d, J=5.1 Hz, 3H) | 213.4, 145.3, 128.4, 127.6, 126.0, 46.3, 43.9, 38.6, 32.4, 30.8, 26.6, 26.3, 23.9, 28.2, 21.5, 21.2, 15.3 |
3d | 7.31—7.18(m, 5H), 3.60—3.56(m, 1H), 3.36(dd, J=12.8, 8.6 Hz, 1H), 2.72—2.66(m, 1H), 2.38(dd, J=12.8, 2.2 Hz, 1H), 1.79—1.64(m, 4H), 1.35—1.18(m, 16H), 0.86(t, J=5.3 Hz, 3H) | 213.2, 145.4, 128.4, 127.6, 126.0, 52.2, 45.2, 38.5, 32.4, 29.9, 29.8, 29.2, 26.5, 24.0, 22.9, 21.8 |
3e | 7.29—7.12(m, 10H), 3.62—3.56(m, 1H), 3.31(dd, 1H, J=17.4, 11.3 Hz), 3.06—2.96(m, 2H), 2.67—2.61(m, 1H), 2.19(dd, 1H, J=17.4, 2.8 Hz), 1.84—1.26(m, 16H) | 212.2, 145.0, 140.2, 128.8, 128.3, 128.2, 127.4, 126.0, 125.9, 53.9, 45.1, 37.9, 36.0, 32.2, 28.8, 26.5, 26.4, 23.8, 22.7, 21.7, 20.7 |
3f | 7.89(d, J=7.2 Hz, 2H), 7.59—7.52(m, 1H), 7.47—7.41(m, 2H), 7.29—7.13(m, 5H), 4.67(dd, 1H, J=9.8, 3.3 Hz), 3.41—3.35(m, 1H), 2.99(dd, 1H, J=16.0, 10.5 Hz), 2.75(dd, 1H, J=16.0, 3.2 Hz), 2.37—2.34(m, 1H), 1.86—1.15(m, 15H) | 205.7, 196.4, 145.1, 136.3, 133.4, 128.8, 128.4, 128.3, 127.3, 126.1, 62.5, 47.48, 40.3, 32.6, 27.8, 26.22, 25.9, 24.8, 23.7, 23.5, 23.0 |
3g | 7.33—7.22(m, 5H), 4.01(dd, J=6.7, 2.9 Hz, 1H), 3.37(s, 3H), 3.23—3.14(m, 1H), 2.53(dd, J=16.6, 3.1 Hz, 1H), 2.03—1.20(m, 16H) | 209.2, 144.5, 128.2, 127.5, 126.1, 86.6, 57.6, 42.4, 38.0, 30.9, 28.5, 26.0, 25.7, 22.4, 22.3, 20.4, 19.3 |
3h | 7.76—7.21(m, 10H), 4.51(dd, J=9.3, 2.2 Hz, 1H), 3.35—3.26(m, 2H), 3.00—2.94(m, 1H), 2.14—1.14(m, 16H) | 201.9, 143.2, 135.9, 134.3, 129.3, 129.0, 128.6, 127.4, 126.7, 126.3, 72.3, 50.5, 38.8, 30.9, 25.7, 25.6, 24.3, 23.0, 22.9, 22.2 |
4 | 8.06—7.96(m, 2H), 7.58—7.39(m, 2H), 5.77—5.71(m, 1H), 5.01(d, J=10.9 Hz,1H), 3.20—3.12(m, 1H), 2.62—2.52(m, 1H), 1.88—1.26(m, 16H) | 204.1, 164.0, 134.6, 133.2, 131.6, 129.8, 129.7, 127.9, 73.8, 37.9, 31.7, 28.6, 25.3, 25.2, 24.3, 24.0, 23.2, 22.0, 19.8 |
Table 2 1H NMR and 13C NMR data of compounds 3a—3f and 4
Compd. | 1H NMR(300 MHz, CDCl3), δ | 13C NMR(75 MHz, CDCl3), δ |
---|---|---|
3a | 7.38—7.20(m, 5H), 4.59(dd, 1H,J=12.2, 3.6 Hz), 3.34—3.26(m, 1H), 3.08(dd, 1H, J=14.4, 3.1 Hz), 2.94(dd, 1H, J=12.2, 14.4 Hz), 2.51—2.42(m, 1H), 2.00—1.93(m, 1H), 1.63—1.08(m, 14H) | 203.8, 143.8, 128.5, 127.4, 126.5, 48.9, 43.9, 39.1, 33.1, 30.9, 24.7, 24.4, 24.2, 23.6, 22.3, 21.9 |
3b | 7.35—7.19(m, 5H), 4.99(dd, 1H, J=11.3, 3.6 Hz), 3.31(dd, 1H, J=13.5, 2.9 Hz), 3.17—3.12(m, 1H), 2.70—2.59(m, 2H), 2.01—1.92(m, 1H), 1.60—1.12(m, 14H) | 204.4, 143.7, 128.6, 127.4, 126.6, 45.9, 40.3, 34.9, 30.8, 25.9, 25.84, 25.81, 23.6, 23.0, 22.8, 22.2 |
3c | 7.30—7.18(m, 5H), 3.61—3.55(m, 1H), 3.33(dd, J=12.7, 8.5 Hz, 1H), 2.86—2.82(m, 1H), 2.37(dd, J=12.7, 2.2 Hz, 1H), 1.81—1.07(m, 16H), 1.06(d, J=5.1 Hz, 3H) | 213.4, 145.3, 128.4, 127.6, 126.0, 46.3, 43.9, 38.6, 32.4, 30.8, 26.6, 26.3, 23.9, 28.2, 21.5, 21.2, 15.3 |
3d | 7.31—7.18(m, 5H), 3.60—3.56(m, 1H), 3.36(dd, J=12.8, 8.6 Hz, 1H), 2.72—2.66(m, 1H), 2.38(dd, J=12.8, 2.2 Hz, 1H), 1.79—1.64(m, 4H), 1.35—1.18(m, 16H), 0.86(t, J=5.3 Hz, 3H) | 213.2, 145.4, 128.4, 127.6, 126.0, 52.2, 45.2, 38.5, 32.4, 29.9, 29.8, 29.2, 26.5, 24.0, 22.9, 21.8 |
3e | 7.29—7.12(m, 10H), 3.62—3.56(m, 1H), 3.31(dd, 1H, J=17.4, 11.3 Hz), 3.06—2.96(m, 2H), 2.67—2.61(m, 1H), 2.19(dd, 1H, J=17.4, 2.8 Hz), 1.84—1.26(m, 16H) | 212.2, 145.0, 140.2, 128.8, 128.3, 128.2, 127.4, 126.0, 125.9, 53.9, 45.1, 37.9, 36.0, 32.2, 28.8, 26.5, 26.4, 23.8, 22.7, 21.7, 20.7 |
3f | 7.89(d, J=7.2 Hz, 2H), 7.59—7.52(m, 1H), 7.47—7.41(m, 2H), 7.29—7.13(m, 5H), 4.67(dd, 1H, J=9.8, 3.3 Hz), 3.41—3.35(m, 1H), 2.99(dd, 1H, J=16.0, 10.5 Hz), 2.75(dd, 1H, J=16.0, 3.2 Hz), 2.37—2.34(m, 1H), 1.86—1.15(m, 15H) | 205.7, 196.4, 145.1, 136.3, 133.4, 128.8, 128.4, 128.3, 127.3, 126.1, 62.5, 47.48, 40.3, 32.6, 27.8, 26.22, 25.9, 24.8, 23.7, 23.5, 23.0 |
3g | 7.33—7.22(m, 5H), 4.01(dd, J=6.7, 2.9 Hz, 1H), 3.37(s, 3H), 3.23—3.14(m, 1H), 2.53(dd, J=16.6, 3.1 Hz, 1H), 2.03—1.20(m, 16H) | 209.2, 144.5, 128.2, 127.5, 126.1, 86.6, 57.6, 42.4, 38.0, 30.9, 28.5, 26.0, 25.7, 22.4, 22.3, 20.4, 19.3 |
3h | 7.76—7.21(m, 10H), 4.51(dd, J=9.3, 2.2 Hz, 1H), 3.35—3.26(m, 2H), 3.00—2.94(m, 1H), 2.14—1.14(m, 16H) | 201.9, 143.2, 135.9, 134.3, 129.3, 129.0, 128.6, 127.4, 126.7, 126.3, 72.3, 50.5, 38.8, 30.9, 25.7, 25.6, 24.3, 23.0, 22.9, 22.2 |
4 | 8.06—7.96(m, 2H), 7.58—7.39(m, 2H), 5.77—5.71(m, 1H), 5.01(d, J=10.9 Hz,1H), 3.20—3.12(m, 1H), 2.62—2.52(m, 1H), 1.88—1.26(m, 16H) | 204.1, 164.0, 134.6, 133.2, 131.6, 129.8, 129.7, 127.9, 73.8, 37.9, 31.7, 28.6, 25.3, 25.2, 24.3, 24.0, 23.2, 22.0, 19.8 |
Compd. | 3d | 3e | 3g | 3h |
---|---|---|---|---|
Crystal size/mm3 | 0.70×0.05×0.04 | 0.50×0.30×0.08 | 0.40×0.25×0.07 | 0.30×0.08×0.05 |
Empirical formula | C22H34O | C25H32O | C19H28O2 | C24H30SO3 |
Formula weight | 314.49 | 348.51 | 288.41 | 398.54 |
Temperature/K | 102.1 | 98.7 | 104.4 | 104.5 |
Crystal system | Momoclinic | Momoclinic | Orthorhombic | Momoclinic |
Space group | P2/n | C2/n | Pbca | P21/c |
a/nm | 1.5910(6) | 2.34299(4) | 1.24310(8) | 1.38599(4) |
b/nm | 0.5535(2) | 0.562885(9) | 1.07820(5) | 1.50455(5) |
c/nm | 2.3010(8) | 3.03128(5) | 2.4889(3) | 0.99769(3) |
α/(°) | 90.00 | 90.00 | 90.00 | 90.00 |
β/(°) | 108.65(4) | 101.0795(16) | 90.00 | 98.324(3) |
γ/(°) | 90.00 | 90.00 | 90.00 | 90.00 |
Volume/nm3 | 1.9197(12) | 3.92324(11) | 3.3359(5) | 2.05857(11) |
Z | 4 | 8 | 8 | 4 |
ρcalc./(g·cm-3) | 1.088 | 1.180 | 1.149 | 1.286 |
μ/mm-1 | 0.064 | 0.0525 | 0.072 | 0.180 |
F(000) | 696 | 1520 | 1264 | 856 |
2θ/(°) | 6.96—52 | 5.94—142.44 | 6.54—52 | 6.06—52 |
Index range | -15≤h≤19 | -22≤h≤28 | -13≤h≤15 | -17≤h≤17 |
-4≤k≤6 | -6≤ k≤6 | -13≤k≤10 | -18≤k≤18 | |
-28≤l≤23 | -37≤l≤36 | -25≤l≤30 | -11≤l≤12 | |
Reflections collected | 7913 | 5892 | 10243 | 9231 |
Independent reflections R(int) | 3768(0.1258) | 6094(0.0000) | 3288(0.0381) | 4038(0.0254) |
Data/restraints/parameters | 3768/0/209 | 6094/0/236 | 3288/0/191 | 4038/16/253 |
GOF | 0.969 | 1.084 | 1.058 | 1.046 |
Final R indices[I>2σ(I)] | R1=0.0872, | R1=0.0464, | R1=0.0479, | R1=0.0554, |
wR2=0.1386 | wR2=0.1242 | wR2=0.0933 | wR2=0.1244 | |
R index(all data) | R1=0.2043, | R1=0.0496, | R1=0.0660, | R1=0.0668, |
wR2=0.1979 | wR2=0.1264 | wR2=0.1016 | wR2=0.1311 | |
Largest diff. peak and hole/(e·nm-3) | 239, -271 | 248, -214 | 198, -198 | 116, -436 |
Completeness | 0.998 | 0.992 | 0.999 | 0.998 |
Table 3 Crystal structure parameters for compounds 3d, 3e, 3g and 3h
Compd. | 3d | 3e | 3g | 3h |
---|---|---|---|---|
Crystal size/mm3 | 0.70×0.05×0.04 | 0.50×0.30×0.08 | 0.40×0.25×0.07 | 0.30×0.08×0.05 |
Empirical formula | C22H34O | C25H32O | C19H28O2 | C24H30SO3 |
Formula weight | 314.49 | 348.51 | 288.41 | 398.54 |
Temperature/K | 102.1 | 98.7 | 104.4 | 104.5 |
Crystal system | Momoclinic | Momoclinic | Orthorhombic | Momoclinic |
Space group | P2/n | C2/n | Pbca | P21/c |
a/nm | 1.5910(6) | 2.34299(4) | 1.24310(8) | 1.38599(4) |
b/nm | 0.5535(2) | 0.562885(9) | 1.07820(5) | 1.50455(5) |
c/nm | 2.3010(8) | 3.03128(5) | 2.4889(3) | 0.99769(3) |
α/(°) | 90.00 | 90.00 | 90.00 | 90.00 |
β/(°) | 108.65(4) | 101.0795(16) | 90.00 | 98.324(3) |
γ/(°) | 90.00 | 90.00 | 90.00 | 90.00 |
Volume/nm3 | 1.9197(12) | 3.92324(11) | 3.3359(5) | 2.05857(11) |
Z | 4 | 8 | 8 | 4 |
ρcalc./(g·cm-3) | 1.088 | 1.180 | 1.149 | 1.286 |
μ/mm-1 | 0.064 | 0.0525 | 0.072 | 0.180 |
F(000) | 696 | 1520 | 1264 | 856 |
2θ/(°) | 6.96—52 | 5.94—142.44 | 6.54—52 | 6.06—52 |
Index range | -15≤h≤19 | -22≤h≤28 | -13≤h≤15 | -17≤h≤17 |
-4≤k≤6 | -6≤ k≤6 | -13≤k≤10 | -18≤k≤18 | |
-28≤l≤23 | -37≤l≤36 | -25≤l≤30 | -11≤l≤12 | |
Reflections collected | 7913 | 5892 | 10243 | 9231 |
Independent reflections R(int) | 3768(0.1258) | 6094(0.0000) | 3288(0.0381) | 4038(0.0254) |
Data/restraints/parameters | 3768/0/209 | 6094/0/236 | 3288/0/191 | 4038/16/253 |
GOF | 0.969 | 1.084 | 1.058 | 1.046 |
Final R indices[I>2σ(I)] | R1=0.0872, | R1=0.0464, | R1=0.0479, | R1=0.0554, |
wR2=0.1386 | wR2=0.1242 | wR2=0.0933 | wR2=0.1244 | |
R index(all data) | R1=0.2043, | R1=0.0496, | R1=0.0660, | R1=0.0668, |
wR2=0.1979 | wR2=0.1264 | wR2=0.1016 | wR2=0.1311 | |
Largest diff. peak and hole/(e·nm-3) | 239, -271 | 248, -214 | 198, -198 | 116, -436 |
Completeness | 0.998 | 0.992 | 0.999 | 0.998 |
Angle | 3d | 3e | 3g | 3h | [ |
---|---|---|---|---|---|
C1—C2—C3—C4 | 154.78 | 157.48 | 150.59 | 145.71 | 148.0 |
C2—C3—C4—C5 | -64.00 | -69.52 | -68.59 | -54.19 | -60.0 |
C3—C4—C5—C6 | -66.52 | -71.23 | -64.22 | 68.87 | -70.0 |
C4—C5—C6—C7 | 168.31 | 169.87 | 175.13 | 178.40 | 176.0 |
C5—C6—C7—C8 | -68.66 | -63.39 | -65.93 | -70.34 | -67.0 |
C6—C7—C8—C9 | -72.66 | -65.32 | -67.62 | -68.46 | -69.0 |
C7—C8—C9—C10 | 154.65 | 152.85 | 144.56 | 139.05 | 146.0 |
C8—C9—C10—C11 | -64.12 | -71.92 | -70.54 | -68.77 | -69.0 |
C9—C10—C11—C12 | -63.34 | -70.63 | -68.91 | -71.28 | -69.0 |
C10—C11—C12—C1 | 169.87 | 168.63 | 174.39 | 171.43 | 172.0 |
C11—C12—C1—C2 | -72.38 | -64.10 | -60.73 | -55.13 | -65.0 |
C12—C1—C2—C3 | -77.71 | -72.90 | -77.07 | -87.00 | -76.0 |
Table 4 Torsional angels(°) of some compounds in the crystal structures and [3333]-2-one conformation
Angle | 3d | 3e | 3g | 3h | [ |
---|---|---|---|---|---|
C1—C2—C3—C4 | 154.78 | 157.48 | 150.59 | 145.71 | 148.0 |
C2—C3—C4—C5 | -64.00 | -69.52 | -68.59 | -54.19 | -60.0 |
C3—C4—C5—C6 | -66.52 | -71.23 | -64.22 | 68.87 | -70.0 |
C4—C5—C6—C7 | 168.31 | 169.87 | 175.13 | 178.40 | 176.0 |
C5—C6—C7—C8 | -68.66 | -63.39 | -65.93 | -70.34 | -67.0 |
C6—C7—C8—C9 | -72.66 | -65.32 | -67.62 | -68.46 | -69.0 |
C7—C8—C9—C10 | 154.65 | 152.85 | 144.56 | 139.05 | 146.0 |
C8—C9—C10—C11 | -64.12 | -71.92 | -70.54 | -68.77 | -69.0 |
C9—C10—C11—C12 | -63.34 | -70.63 | -68.91 | -71.28 | -69.0 |
C10—C11—C12—C1 | 169.87 | 168.63 | 174.39 | 171.43 | 172.0 |
C11—C12—C1—C2 | -72.38 | -64.10 | -60.73 | -55.13 | -65.0 |
C12—C1—C2—C3 | -77.71 | -72.90 | -77.07 | -87.00 | -76.0 |
Compd. | Relative energy/(kJ·mol-1) | ||||
---|---|---|---|---|---|
Conformation A | Conformation B | Conformation C | Conformation D | Conformation E | |
3a | 0.00 | 3.01 | 17.42 | 9.85 | 1.09 |
3b | 10.44 | 23.31 | 27.62 | 35.66 | 0.00 |
3c | 0.00 | 6.93 | 5.81 | 13.52 | 3.58 |
3d | 0.00 | 24.43 | 30.53 | 31.20 | 20.24 |
3e | 0.00 | 6.20 | 673.83 | 1041.40 | 583.55 |
3f | 0.00 | 1168.61 | 201.46 | 126.15 | 214.91 |
3g | 0.00 | 3.82 | 21.10 | 9.77 | 30.86 |
3h | 9.62 | 11.81 | 17.41 | 22.23 | 0.00 |
Table 5 Relative energy(kJ/mol) of conformation for compounds 3a—3h by quantum mechanics
Compd. | Relative energy/(kJ·mol-1) | ||||
---|---|---|---|---|---|
Conformation A | Conformation B | Conformation C | Conformation D | Conformation E | |
3a | 0.00 | 3.01 | 17.42 | 9.85 | 1.09 |
3b | 10.44 | 23.31 | 27.62 | 35.66 | 0.00 |
3c | 0.00 | 6.93 | 5.81 | 13.52 | 3.58 |
3d | 0.00 | 24.43 | 30.53 | 31.20 | 20.24 |
3e | 0.00 | 6.20 | 673.83 | 1041.40 | 583.55 |
3f | 0.00 | 1168.61 | 201.46 | 126.15 | 214.91 |
3g | 0.00 | 3.82 | 21.10 | 9.77 | 30.86 |
3h | 9.62 | 11.81 | 17.41 | 22.23 | 0.00 |
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