3-1 分析儀器及實驗操作
1. 核磁共振光譜：核磁共振儀（Nuclear Magnetic Resonance Spectroscopy，NMR Spectroscopy）廠牌：Bruker，型號：Bruker Avance 型（400 MHz），樣品溶劑 為氘化氯仿（CDCl3）。化學位移（δ，chemical shift），單位為 ppm，1H-NMR 光譜化學位移以四甲基矽烷（tetramethylsilane，TMS）為內標準品，定義其化 學位移為0 ppm。分裂形式（splitting pattern）定義如下：s，單重峰（singlet）； d，雙重峰（doublet）；t，三重峰（triplet），q，四重峰（quartet）；m，多重峰
（multiplet）。耦合常數（coupling constant）以 J 表示，單位為 Hz。光譜數據 紀錄依序為：化學位移（分裂形式，耦合常數，氫數）。13C-NMR 光譜是以 同樣儀器操作，化學位移以氘化氯仿中間線為內標準，定義其化學位移為77.0 ppm。
2. 高解析質譜：高解析質譜分析儀（High Resolution Mass Spectrometer，HRMS）， 廠牌：JEOL，型號：JMS- 700，係委託科系部臺灣師範大學貴重儀器中心代 為測定。
3. X 光單晶繞射圖：Bruker D8 Venture 雙鈀 X-射線單晶繞射儀（Bruker D8 Venture Dual X-ray Single Crystal Diffractometer，D8 Venture），廠牌：Bruker ， 型號：D8 Venture IuS 3.0 Dual source。係委託科系部臺灣師範大學貴重儀器 中心代為測定。
4. 薄層層析（Thin Layer Chromatography，TLC）之分析片，Silica gel 60 F254 Merck 之玻璃 TLC 薄片，以展層液展開後，利用紫外燈（254 nm）檢視。
5. 管柱層析（Column Chromatography）以 Merck Silica gel F60，230-400 mesh ATSM 為填充物，用加壓快速層析（flash column chromatography）依操作方 法來分離。沖提液（eluent）若以兩種以上溶劑，以體積比配置，紀錄溶劑體 積比。（J. Org. Chem. 1978, 43, 2923）
56
6. 反應物皆以管柱層析純化，溶劑均為試藥級、分析級或高效能液相層析級。
7. 減壓式迴旋濃縮：使用 Büchi Rotavapor R-114 、 R-200、R-II 型旋轉濃縮器，
連接空氣式幫浦。
8. 低溫反應控制裝置：使用 NES-LAB Cryobath CB-80 型低溫控制裝置與 UR-8500/5000 超低溫反應器，以工業級異丙醇與丙酮為冷劑。
9. 紅外線光譜：紅外線光譜儀（IR Spectroscopy），型號：Perkin Elmer FTIR 500。
10. 熔點：熔點儀器，型號：MEL-TEMP II
57
3-2 有機連鎖 Michael/acetalization/oxa-Michael 反應之實驗步驟
OH
Synthesis of multi-Substituted tetrahydrofurano benzopyran scaffold：
To the stirred solution of 1-(2’-hydroxyphenyl)butane-1,3-dione 129a (20.0 mg, 0.11 mmol) and nitroallylic acetate 57 (35.0 mg, 0.12 mmol) in DCE (1.0 mL) at -20 ºC.
After 30 mins, the trimethylamine (16.8, µL, 0.12 mmol) was added to mixture. The reaction was monitored by TLC until starting material was not comsumed. Then the reaction mixture was quenched by H2O (20 mL) and extracted with DCM (20 x 2 mL).
The organic layer was dried over with MgSO4.The 1H-NMR yield was detected from crude by NMR. The solvent was evaporated under reduced pressure. The crude was purified by flash column chromatography (hexane /ethyl acetaye =1:8 to 1:4) to afford the major product 132a moderate yield and the minor product 133a.
58
3-3 光譜數據 Compound 132a
Colorless solid; reaction time: 13 h; yield: 55%; Rf = 0.23 (1:5
= EtOAc:Hex); decomposition temperature = 159.2-160.5 ºC;
1H NMR (400 MHz, CDCl3) δ = 7.77 (dd, J = 8.0, 1.2 Hz, 1H), 7.57 (td, J = 7.8, 1.2 Hz, 1H), 7.40-7.31 (m, 3H), 7.24-7.21 (m, 2H), 7.06 (t, J =7.6 Hz, 1H), 7.02 (d, J = 8.4 Hz, 1H), 4.28 (d, J = 13.5 Hz, 1H), 4.20 (m, 2H), 3.89 (d, J = 13.6, 1H), 3.54 (d, J = 16.0 Hz, 1H), 3.22 (d, J = 16.0 Hz, 1H), 1.96 (s, 3H), 1.26 (t, J = 7.1 Hz, 3H) ppm; 13C NMR (100 MHz, CDCl3) δ =189.2, 167.1, 157.6, 137.4, 129.6, 129.5, 129.1, 128.1, 127.4, 122.5, 118.2, 117.3, 116.8, 113.9, 61.6, 55.1, 53.7, 40.1, 22.6, 14.0 ppm; IR (CHCl3) ν = 2985, 1738, 1688, 1606, 1564, 1464, 1380, 1310, 1216, 1028, 752 127.4, 125.5, 122.6, 118.2, 117.3, 116.7, 116.4, 116.2, 113.7, 61.7, 54.2, 53.9, 39.9, 22.6, 14.0 ppm; IR (CHCl3) ν = 2987, 1743, 1690, 1606, 1561, 1465, 1380, 1312, 1261, 1221, 753 cm-1; HRMS (ESI) m/z calcd for C22H20FNO7Na: 452.1116 [M+Na]+; found:
452.1121.
59
Compound 132c
Colorless solid; reaction time: 9 h; yield: 51%; Rf = 0.25 (1:5
= EtOAc:Hex); decomposition temperature = 142.0-148.0 ºC;
1H NMR (400 MHz, CDCl3) δ = 7.78 (dd, J = 8.0, 1.4 Hz, 1H), 7.58 (td, J = 8.0, 1.4 Hz, 1H), 7.34 (d, J = 8.8 Hz, 2H), 7.19 (d, J = 8.4 Hz, 2H), 7.07 (t, J =7.6 Hz, 1H), 7.02 (d, J = 8.4 Hz, 1H), 4.30 (d, J = 13.5 Hz, 1H), 4.20 (m, 2H), 3.81 (d, J = 13.5 Hz, 1H), 3.49 (d, J = 15.8 Hz, 1H), 3.21 (d, J
= 15.8, 1H), 1.96 (s, 3H), 1.26 (t, J = 7.1 Hz, 3H) ppm; 13C NMR (100 MHz, CDCl3) δ
= 189.0, 167.0, 157.6, 137.5, 135.7, 129.5, 129.4, 128.2, 127.4, 122.6, 118.2, 117.3, 116.7, 113.8, 61.7, 54.2, 53.7, 39.9, 22.6, 14.0 ppm; IR (CHCl3) ν = 2986, 1743, 1690, δ = 189.0, 167.0, 157.6, 137.5, 132.4, 129.8, 128.7, 127.4, 123.9, 122.6, 118.2, 117.2, 116.6, 113.7, 61.7, 54.3, 53.7, 39.9, 22.6, 14.0 ppm; IR (CHCl3) ν = 2985, 1743, 1689,
60 148.5, 137.8, 137.0, 129.4, 127.4, 124.2, 122.8, 118.3, 117.2, 116.7, 113.7, 61.9, 53.8, 53.7, 39.8, 22.6, 14.0 ppm; IR (CHCl3) ν = 2927, 1744, 1690, 1606, 1563, 1528, 1465, 2986, 1745, 1690, 1606, 1563, 1465, 1380, 1316, 1217, 1034, 753 cm-1; HRMS (ESI) m/z calcd for C23H23NO7Na: 448.1367 [M+Na]+; found: 448.1373.
61
Compound 132g
Yellow solid; reaction time: 20 h; yield: 59%; Rf = 0.20 (1:5 = EtOAc:Hex); decomposition temperature = 138.0-143.6 ºC;
1H NMR (400 MHz, CDCl3) δ = 7.77 (dd, J = 8.0, 1.6 Hz, 1H), 7.57 (td, J = 7.8, 1.6 Hz, 1H), 7.15 (d, J = 8.8 Hz, 2H), 7.05 (t, J = 7.6 Hz, 1H), 7.01 (d, J = 8.4 Hz, 1H), 6.88 (d, J = 8.4 Hz, 2H), 4.22 (d, J = 13.6 Hz, 1H), 4.20 (m, 2H), 3.82 (d, J = 13.2 Hz, 1H), 3.78 (s, 3H), 3.53 (d, J = 16.0 Hz, 1H), 3.19 (d, J = 16.0 Hz, 1H), 1.95 (s, 3H), 1.26 (t, J = 7.2 Hz, 3H) ppm; 13C NMR (100 MHz, CDCl3) δ =189.3, 167.1, 160.4, 157.7, 137.3, 129.3, 127.4, 122.4, 121.3, 118.2, 117.3, 116.7, 114.6, 113.8, 61.6, 55.2, 54.7, 54.0, 40.1, 22.7, 14.0 ppm; IR (CHCl3) ν = 2929, 1746, 1690, 1606, 1563, 1464, 1379, 1356, 1311, 1258, 1218, 1031, 752 cm-1; HRMS (ESI) m/z calcd for C23H23NO8Na: 464.1316 [M+Na]+; found: 464.1324.
Compound 132h
Colorless solid; reaction time: 16 h; yield: 47%; Rf = 0.20 (1:5
= EtOAc:Hex); decomposition temperature = 164.0-166.1 ºC;
1H NMR (400 MHz, CDCl3) δ = 7.78 (dd, J = 8.0, 1.6 Hz, 1H), 131.8, 130.7, 127.4, 126.3, 123.0, 122.6, 118.2, 117.2, 116.6, 113.7, 61.7, 54.3, 53.6, 40.0, 22.6, 14.0 ppm; IR (CHCl3) ν = 2987, 1742, 1686, 1606, 1561, 1465, 1380, 1311, 1260, 1218, 1033, 754 cm-1; HRMS (ESI) m/z calcd for C22H20BrNO7Na: 512.0315 [M+Na]+; found: 512.0321.
62
Compound 132i
Colorless solid; reaction time: 20 h; yield: 52%; Rf = 0.21 (1:5
= EtOAc:Hex); decomposition temperature = 164.8-165.7 ºC;
1H NMR (400 MHz, CDCl3) δ = 7.78 (dd, J = 7.8, 1.4 Hz, 1H), 159.9, 157.6, 137.4, 131.0, 130.1, 127.4, 122.5, 120.2, 118.2, 117.3, 116.7, 114.7, 114.3, 113.8, 61.6, 55.2, 55.1, 53.8, 40.2, 22.6, 14.0 ppm; IR (CHCl3) ν = 2983, 1736, 1687, 1606, 1561, 1464, 1380, 1311, 1259, 1219, 1032, 749 cm-1; HRMS (ESI) m/z calcd for C23H23NO8Na: 464.1316 [M+Na]+; found: 464.1323. 189.5, 167.5, 157.8, 137.2, 130.4, 127.4, 122.3, 121.2, 118.4, 118.1, 117.5, 116.9, 113.9, 110.5, 61.2, 55.3, 53.3, 41.4, 22.7, 14.0 ppm; IR (CHCl3) ν = 2985, 1745, 1689, 1606, 1564, 1496, 1464, 1378, 1354, 1311, 1257, 1219, 1030, 754 cm-1; HRMS (ESI) m/z calcd for C23H23NO8Na: 464.1316 [M+Na]+; found: 464.1324.
63
Compound 133a
Colorless liquid; reaction time: 13 h; yield: 13%; Rf = 0.45 (1:5 = EtOAc:Hex); 1H NMR (400 MHz, CDCl3) δ = 12.03 (s, 1H), 7.45 (dd, J = 8.0, 1.6 Hz, 1H), 7.34 (td, J = 7.8, 1.6 Hz, 1H), 7.30-7.22 (m, 2H), 7.21-7.15 (m, 3H), 6.92 (d, J = 8.4 Hz, 1H), 6.23 (t, J = 7.6 Hz, 1H), 4.22 (q, J = 7.2 Hz, 2H), 3.68 (s, 2H), 2.37 (s, 3H), 1.30 (t, J = 7.2 Hz, 3H) ppm; 13C NMR (100 MHz, CDCl3) δ =197.0, 169.4, 162.5, 154.2, 143.1, 136.3, 133.2, 131.6, 129.0, 128.5, 127.3, 124.5, 121.2, 120.1, 118.5, 117.8, 61.4, 32.6, 14.1, 13.5 ppm; IR (CHCl3) ν = 2928, 1736, 1604, 1346, 1186, 1151, 758 cm-1; HRMS (ESI) m/z calcd for C22H21O5: 365.1384 [M+H]+; found: 365.1389.
64
65
第四章 參考文獻
1. https://en.wikipedia.org/wiki/Chemistry.
2. https://en.wikipedia.org/wiki/Organic_chemistry.
3. https://en.wikipedia.org/wiki/Thalidomide.
4. https://en.wikipedia.org/wiki/Organic_synthesis.
5. U. Eder, G. Sauer, R. Wiechert, Angew. Chem. Int. Ed. 1971, 83, 492.
6. Z. G. Hajos, D. R. Parrish, J. Org. Chem. 1974, 39, 1615.
7. https://en.wikipedia.org/wiki/Enantioselective_synthesis.
8. P. G. Gassman, T. J. V. Bergen, D. P. Gilbert, B. W. Cue, J. Am. Chem. Soc. 1974, 96, 5495.
9. L. F. Tietze, Chem. Rev. 1996, 96, 115.
10. W.-D. Fessner, G. Sedelmeier, P. R. Spurr, G. Rihs, H. Prinzbach, J. Am. Chem.
Soc. 1987, 109, 4626.
11. T. Bui and C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951.
12. H. Pellissier, Adv. Synth. Catal. 2012, 354, 237.
13. D. Enders, M. R. M. Hüttl, C. Grondal, G. Raabe, Nature 2006, 441, 861.
14. S. E. Denmark, A. Thorarensen, Chem. Rev. 1996, 96, 137.
15. G. A. Kraus, M. J. Taschner, J. Am. Chem. Soc. 1980, 102, 1974.
16. E. Knoevenagel, Ber. Dtsch. Chem. Ges.1898, 31, 2596.
17. H. Pracejus, Justus Liebigs Ann. Chem. 1960, 634, 9.
18. D. W. C. MacMillan, Nature 2008, 455, 304.
19. D. W. C. MacMillan, G. Lelais, Aldrichim. Acta 2006, 39, 79.
20. M. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 4901.
21. K. Morita, Z. Suzuki, H. Hirose, Chem. Soc. Jpn. 1968, 41, 2815.
22. A. B. Baylis, M. E. D. Hillman, German Patent 2155113, 1972.
66
23. S. Chandrasekhar, K. Mallikarjun, G. Pavankumarreddy, K. V. Rao, B. Jagadeesh, Chem. Commun. 2009, 4985.
24. W.-Y. Huang, S. Anwar, K. Chen, Chem. Rec. 2017, 17, 363.
25. D. K. Nair, S. M. Mobin, I. N.N. Namboothiri, Tetrahedron Lett. 2012, 53, 3349.
26. S. Anwar, W.-Y. Huang, C.-H. Chen, Y.-S. Cheng, K. Chen, Chem. Eur. J. 2013, 19, 4344.
27. H. Zhu, N. Shao, T. Chen H. Zou, Chem. Commun., 2013, 49, 7738.
28. A. Ichihara, M. Nonaka, S. Sakamura, R. Sato, A. Tajimi, Chem. Lett. 1988, 27.
29. Y. Lin, X. Wu, S. Feng, G. Jiang, J. Luo, S. Zhou, L. L. P. Vrijmoed, E. B. G.
Jones, K. Krohn, K. Steingröver, F. Zsila, J. Org. Chem. 2001, 66, 6252.
30. H. Gong, Z. Luo,W. Chen, Z.-P. Feng, G.-L. Wang, H.-S. Sun, Mar. Drugs 2018, 16, 516.
31. P. J. Cremins, T. W. Wallace, J. Chem. Soc., Chem. Commun. 1984, 1698.
32. L. Diao, C. Yang, P. Wan, J. Am. Chem. Soc. 1995, 117, 5369.
33. J. S. Yadav, B. V. Subba Reddy, Ch. Madhuri, G. Sabitha, B. Jagannadh, S. Kiran Kumarb, A. C. Kunwar, Tetrahedron Lett. 2001, 42, 6381.
34. M. Anniyappan, D. Muralidharan, P. T. Perumal, Tetrahedron 2002, 58, 10301.
35. J. Wang, F.-X. Xu, X.-F. Lin , Y.-G. Wang, Tetrahedron Lett. 2008, 49, 5208.
36. S. R. Graham, J. A. Murphy, A. R. Kennedy, J. Chem. Soc., Perkin Trans. 1 1999, 3071.
37. R. Rodriguez, R. M. Adlington, J. E. Moses, A.Cowley, J. E. Baldwin, Org. Lett.
2004, 6, 3617.
38. J. D. Pettigrew, J. A. Bexrud, R. P. Freeman, P. D. Wilson, HeteroCycle 2004, 62, 445.
39. I. Deb, M. Dadwal, S. M. Mobin, I. N. N. Namboothiri, Org Lett. 2006, 8, 1201.
40. H.-H. Kuan, R. J. Reddy, K. Chen, Tetrahedron 2010, 66, 9875.
67
41. A. Nishinaga, H. Ando, K. Maruyama, T. Mashino, Synthesis 1992, 839.
42. T. Patonay, A. Vasas, A. Kiss-Szikszai, A. M. S. Silva, and J. A. S. Cavaleiro, Aust.
J. Chem. 2010, 63, 1582.
43. J. E. Baldwin, J. Chem. Soc., Chem. Commun. 1976, 734.
44. M. Karplus, J. Chem. Phys. 1959, 30, 11.
45. M. Karplus, J. Am. Chem. Soc. 1963, 85, 2870.
68
69
附錄一、
1 H-NMR、 13 C-NMR、
DEPT-135及DEPT-90光譜
70
71
72
73
74
75
76
77
78
OO
O NO2 CO2Et 132d
H
Br
79
80
81
82
83
84
OO
O NO2 CO2Et 132g
H
OMe
85
86
87
88
OO
O NO2 CO2Et 132i
H
OMe
89
90
91
92
93
94
95
96
97
附錄二、
X-ray 結構解析與數據
98 Crystal structure and data for compound 132a:
O O
O
NO2
132a H
O O
99
Table 1. Crystal data and structure refinement for d21274.
Identification code d21274
Empirical formula C22 H21 N O7
Formula weight 411.40
Temperature 200(2) K
Wavelength 0.71073 Å
Crystal system Monoclinic
Space group P 21/n
Unit cell dimensions a = 10.2978(4) Å a= 90°.
b = 10.6251(5) Å b= 90.255(2)°.
c = 18.2123(7) Å g = 90°.
Volume 1992.68(14) Å3
Z 4
Density (calculated) 1.371 Mg/m3
Absorption coefficient 0.103 mm-1
F(000) 864
Crystal size 0.47 x 0.41 x 0.27 mm3
Theta range for data collection 2.22 to 25.07°.
Index ranges -12<=h<=12, -12<=k<=12, -21<=l<=21
Reflections collected 29819
Independent reflections 3522 [R(int) = 0.0715]
Completeness to theta = 25.07° 99.3 %
Absorption correction multi-scan
Max. and min. transmission 0.9727 and 0.9532
Refinement method Full-matrix least-squares on F2
Data / restraints / parameters 3522 / 0 / 273
Goodness-of-fit on F2 1.052
Final R indices [I>2sigma(I)] R1 = 0.0390, wR2 = 0.0886
R indices (all data) R1 = 0.0504, wR2 = 0.0962
Largest diff. peak and hole 0.213 and -0.196 e.Å-3
100
Table 2. Atomic coordinates ( x 104) and equivalent isotropic displacement parameters (Å2x 103) for d21274. U(eq) is defined as one third of the trace of the orthogonalized Uij tensor.
________________________________________________________________________________
101
102
O(5)-C(1)-C(2) 111.76(13) O(5)-C(1)-N(1) 106.54(11) C(2)-C(1)-N(1) 108.40(12) O(5)-C(1)-C(16) 107.19(11) C(2)-C(1)-C(16) 114.72(12) N(1)-C(1)-C(16) 107.86(11) C(3)-C(2)-C(1) 113.78(13)
C(3)-C(2)-H(2A) 108.8
C(1)-C(2)-H(2A) 108.8
C(3)-C(2)-H(2B) 108.8
C(1)-C(2)-H(2B) 108.8
H(2A)-C(2)-H(2B) 107.7 O(3)-C(3)-O(4) 124.56(15) O(3)-C(3)-C(2) 125.75(14) O(4)-C(3)-C(2) 109.69(13) O(4)-C(4)-C(5) 108.07(14)
O(4)-C(4)-H(4A) 110.1
C(5)-C(4)-H(4A) 110.1
O(4)-C(4)-H(4B) 110.1
103
C(5)-C(4)-H(4B) 110.1
H(4A)-C(4)-H(4B) 108.4
C(4)-C(5)-H(5A) 109.5
C(4)-C(5)-H(5B) 109.5
H(5A)-C(5)-H(5B) 109.5
C(4)-C(5)-H(5C) 109.5
H(5A)-C(5)-H(5C) 109.5 H(5B)-C(5)-H(5C) 109.5 O(5)-C(6)-O(6) 103.44(11) O(5)-C(6)-C(7) 108.93(13) O(6)-C(6)-C(7) 109.71(12) O(5)-C(6)-C(15) 105.58(12) O(6)-C(6)-C(15) 110.50(12) C(7)-C(6)-C(15) 117.64(13)
C(6)-C(7)-H(7A) 109.5
C(6)-C(7)-H(7B) 109.5
H(7A)-C(7)-H(7B) 109.5
C(6)-C(7)-H(7C) 109.5
H(7A)-C(7)-H(7C) 109.5 H(7B)-C(7)-H(7C) 109.5 O(6)-C(8)-C(9) 117.25(15) O(6)-C(8)-C(13) 122.27(14) C(9)-C(8)-C(13) 120.47(15) C(10)-C(9)-C(8) 119.08(18)
C(10)-C(9)-H(9) 120.5
C(8)-C(9)-H(9) 120.5
C(9)-C(10)-C(11) 121.44(17) C(9)-C(10)-H(10) 119.3 C(11)-C(10)-H(10) 119.3 C(12)-C(11)-C(10) 119.25(17) C(12)-C(11)-H(11) 120.4 C(10)-C(11)-H(11) 120.4 C(11)-C(12)-C(13) 120.54(17) C(11)-C(12)-H(12) 119.7 C(13)-C(12)-H(12) 119.7 C(8)-C(13)-C(12) 119.10(15) C(8)-C(13)-C(14) 119.52(14) C(12)-C(13)-C(14) 121.32(15)
104
O(7)-C(14)-C(13) 122.61(14) O(7)-C(14)-C(15) 121.24(14) C(13)-C(14)-C(15) 116.15(13) C(6)-C(15)-C(14) 113.94(12) C(6)-C(15)-C(16) 101.79(11) C(14)-C(15)-C(16) 114.26(12) C(6)-C(15)-H(15) 108.8 C(14)-C(15)-H(15) 108.8 C(16)-C(15)-H(15) 108.8 C(17)-C(16)-C(15) 117.65(12) C(17)-C(16)-C(1) 116.62(12) C(15)-C(16)-C(1) 100.42(11) C(17)-C(16)-H(16) 107.1 C(15)-C(16)-H(16) 107.1 C(1)-C(16)-H(16) 107.1 C(22)-C(17)-C(18) 118.44(15) C(22)-C(17)-C(16) 119.16(14) C(18)-C(17)-C(16) 122.40(14) C(19)-C(18)-C(17) 120.50(16) C(19)-C(18)-H(18) 119.7 C(17)-C(18)-H(18) 119.7 C(20)-C(19)-C(18) 120.44(18) C(20)-C(19)-H(19) 119.8 C(18)-C(19)-H(19) 119.8 C(21)-C(20)-C(19) 119.45(17) C(21)-C(20)-H(20) 120.3 C(19)-C(20)-H(20) 120.3 C(20)-C(21)-C(22) 120.48(17) C(20)-C(21)-H(21) 119.8 C(22)-C(21)-H(21) 119.8 C(21)-C(22)-C(17) 120.70(17) C(21)-C(22)-H(22) 119.6 C(17)-C(22)-H(22) 119.7 O(2)-N(1)-O(1) 124.59(13) O(2)-N(1)-C(1) 117.59(12) O(1)-N(1)-C(1) 117.68(12) C(3)-O(4)-C(4) 117.05(13) C(1)-O(5)-C(6) 110.98(11)
105
C(8)-O(6)-C(6) 115.40(12)
_____________________________________________________________
Symmetry transformations used to generate equivalent atoms:
106
107