Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2018 Supplementary Material Anti-inflammatory fusicoccane-type diterpenoids from the phytopathogenic fungus Alternaria brassicicola Fengli Li, a, Weiguang Sun, a, Jiankun Guan, b, Yuanyuan Lu, b Shuang Lin, a Sitian Zhang, a Weixi Gao, a Junjun Liu, a Guang Du, b Jianping Wang, a ucheng Zhu, a Changxing Qi, a, * Zhengxi u, a, * and Yonghui Zhang a, * a ubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, uazhong University of Science and Technology, Wuhan 430030, People s Republic of China b Tongji ospital Affiliated to Tongji Medical College, uazhong University of Science and Technology, Wuhan 430030, People s Republic of China * Correspondence: zhangyh@mails.tjmu.edu.cn (Y. Zhang); hzx616@126.com (Z. u); kingqcx@sina.cn (C. Qi).
CNTENTS Figure S1. 1 NMR spectrum of compound 1 (Recorded in methanol-d 4 )...1 Figure S2. 13 C NMR spectrum of compound 1 (Recorded in methanol-d 4 )...2 Figure S3. DEPT spectrum of compound 1 (Recorded in methanol-d 4 )...3 Figure S4. SQC spectrum of compound 1 (Recorded in methanol-d 4 )...4 Figure S5. MBC spectrum of compound 1 (Recorded in methanol-d 4 )...5 Figure S6. 1 1 CSY spectrum of compound 1 (Recorded in methanol-d 4 )...6 Figure S7. NESY spectrum of compound 1 (Recorded in methanol-d 4 )...7 Figure S8. RESIMS spectrum of compound 1...8 Figure S9. UV spectrum of compound 1...8 Figure S10. IR spectrum of compound 1...9 Figure S11. 1 NMR spectrum of compound 2 (Recorded in methanol-d 4 )...10 Figure S12. 13 C NMR spectrum of compound 2 (Recorded in methanol-d 4 )...11 Figure S13. DEPT spectrum of compound 2 (Recorded in methanol-d 4 )...12 Figure S14. SQC spectrum of compound 2 (Recorded in methanol-d 4 )...13 Figure S15. MBC spectrum of compound 2 (Recorded in methanol-d 4 )...14 Figure S16. 1 1 CSY spectrum of compound 2 (Recorded in methanol-d 4 )...15 Figure S17. NESY spectrum of compound 2 (Recorded in methanol-d 4 )...16 Figure S18. RESIMS spectrum of compound 2...17 Figure S19. UV spectrum of compound 2...17 Figure S20. IR spectrum of compound 2...18 Figure S21. 1 NMR spectrum of compound 3 (Recorded in methanol-d 4 )...19 Figure S22. 13 C NMR spectrum of compound 3 (Recorded in methanol-d 4 )...20 Figure S23. DEPT spectrum of compound 3 (Recorded in methanol-d 4 )...21 Figure S24. SQC spectrum of compound 3 (Recorded in methanol-d 4 )...22
Figure S25. MBC spectrum of compound 3 (Recorded in methanol-d 4 )...23 Figure S26. 1 1 CSY spectrum of compound 3 (Recorded in methanol-d 4 )...24 Figure S27. NESY spectrum of compound 3 (Recorded in methanol-d 4 )...25 Figure S28. RESIMS spectrum of compound 3...26 Figure S29. UV spectrum of compound 3...26 Figure S30. IR spectrum of compound 3...27 Figure S31. 1 NMR spectrum of compound 4 (Recorded in methanol-d 4 )...28 Figure S32. 13 C NMR spectrum of compound 4 (Recorded in methanol-d 4 )...29 Figure S33. DEPT spectrum of compound 4 (Recorded in methanol-d 4 )...30 Figure S34. SQC spectrum of compound 4 (Recorded in methanol-d 4 )...31 Figure S35. MBC spectrum of compound 4 (Recorded in methanol-d 4 )...32 Figure S36. 1 1 CSY spectrum of compound 4 (Recorded in methanol-d 4 )...33 Figure S37. NESY spectrum of compound 4 (Recorded in methanol-d 4 )...34 Figure S38. RESIMS spectrum of compound 4...35 Figure S39. UV spectrum of compound 4...36 Figure S40. IR spectrum of compound 4...37 Figure S41. 1 NMR spectrum of compound 5 (Recorded in methanol-d 4 )...38 Figure S42. 13 C NMR spectrum of compound 5 (Recorded in methanol-d 4 )...39 Figure S43. DEPT spectrum of compound 5 (Recorded in methanol-d 4 )...40 Figure S44. SQC spectrum of compound 5 (Recorded in methanol-d 4 )...41 Figure S45. MBC spectrum of compound 5 (Recorded in methanol-d 4 )...42 Figure S46. 1 1 CSY spectrum of compound 5 (Recorded in methanol-d 4 )...43 Figure S47. NESY spectrum of compound 5 (Recorded in methanol-d 4 )...44 Figure S48. RESIMS spectrum of compound 5...45 Figure S49. UV spectrum of compound 5...46
Figure S50. IR spectrum of compound 5...47 Figure S51. 1 NMR spectrum of compound 6 (Recorded in methanol-d 4 )...48 Figure S52. 13 C NMR spectrum of compound 6 (Recorded in methanol-d 4 )...49 Figure S53. DEPT spectrum of compound 6 (Recorded in methanol-d 4 )...50 Figure S54. SQC spectrum of compound 6 (Recorded in methanol-d 4 )...51 Figure S55. MBC spectrum of compound 6 (Recorded in methanol-d 4 )...52 Figure S56. 1 1 CSY spectrum of compound 6 (Recorded in methanol-d 4 )...53 Figure S57. NESY spectrum of compound 6 (Recorded in methanol-d 4 )...54 Figure S58. RESIMS spectrum of compound 6...55 Figure S59. UV spectrum of compound 6...56 Figure S60. IR spectrum of compound 6...57 Figure S61. 1 NMR spectrum of compound 7 (Recorded in methanol-d 4 )...58 Figure S62. 13 C NMR spectrum of compound 7 (Recorded in methanol-d 4 )...59 Figure S63. DEPT spectrum of compound 7 (Recorded in methanol-d 4 )...60 Figure S64. SQC spectrum of compound 7 (Recorded in methanol-d 4 )...61 Figure S65. MBC spectrum of compound 7 (Recorded in methanol-d 4 )...62 Figure S66. 1 1 CSY spectrum of compound 7 (Recorded in methanol-d 4 )...63 Figure S67. NESY spectrum of compound 7 (Recorded in methanol-d 4 )...64 Figure S68. RESIMS spectrum of compound 7...65 Figure S69. UV spectrum of compound 7...65 Figure S70. IR spectrum of compound 7...66 Figure S71. 1 NMR spectrum of compound 8 (Recorded in methanol-d 4 )...67 Figure S72. 13 C NMR spectrum of compound 8 (Recorded in methanol-d 4 )...68 Figure S73. DEPT spectrum of compound 8 (Recorded in methanol-d 4 )...69 Figure S74. SQC spectrum of compound 8 (Recorded in methanol-d 4 )...70
Figure S75. MBC spectrum of compound 8 (Recorded in methanol-d 4 )...71 Figure S76. 1 1 CSY spectrum of compound 8 (Recorded in methanol-d 4 )...72 Figure S77. NESY spectrum of compound 8 (Recorded in methanol-d 4 )...73 Figure S78. RESIMS spectrum of compound 8...74 Figure S79. 1 NMR spectrum of the (S)-MTPA ester of 6 in CDCl 3....75 Figure S80. 1 1 CSY spectrum of the (S)-MTPA ester of 6 in CDCl 3....76 Figure S81. 1 NMR spectrum of the (R)-MTPA ester of 6 in CDCl 3....77 Figure S82. 1 1 CSY spectrum of the (R)-MTPA ester of 6 in CDCl 3...78 Table S1. Experimental and Calculated 13 C NMR Data for three possible structures of 8 (δ in ppm)...79 13 C NMR Calculation Data...80
1 Figure S1. 1 NMR spectrum of compound 1 (Recorded in methanol-d 4 ) 1
1 Figure S2. 13 C NMR spectrum of compound 1 (Recorded in methanol-d 4 ) 2
1 Figure S3. DEPT spectrum of compound 1 (Recorded in methanol-d 4 ) 3
1 Figure S4. SQC spectrum of compound 1 (Recorded in methanol-d 4 ) 4
1 Figure S5. MBC spectrum of compound 1 (Recorded in methanol-d 4 ) 5
1 Figure S6. 1 1 CSY spectrum of compound 1 (Recorded in methanol-d 4 ) 6
1 Figure S7. NESY spectrum of compound 1 (Recorded in methanol-d 4 ) 7
Figure S8. RESIMS spectrum of compound 1 1 Figure S9. UV spectrum of compound 1 8
1 Figure S10. IR spectrum of compound 1 9
2 Figure S11. 1 NMR spectrum of compound 2 (Recorded in methanol-d 4 ) 10
2 Figure S12. 13 C NMR spectrum of compound 2 (Recorded in methanol-d 4 ) 11
2 Figure S13. DEPT spectrum of compound 2 (Recorded in methanol-d 4 ) 12
2 Figure S14. SQC spectrum of compound 2 (Recorded in methanol-d 4 ) 13
2 Figure S15. MBC spectrum of compound 2 (Recorded in methanol-d 4 ) 14
2 Figure S16. 1 1 CSY spectrum of compound 2 (Recorded in methanol-d 4 ) 15
2 Figure S17. NESY spectrum of compound 2 (Recorded in methanol-d 4 ) 16
Intens. x10 4 1.5 1+ 387.2147 LYY3-26-2.d: +MS, 0.0-0.1min #1-5 1.0 0.5 0.0 297.1790 315.1967 347.2210 360.3233 376.2577 300 320 340 360 380 400 420 440 m/z Figure S18. RESIMS spectrum of compound 2 1+ 403.1904 1+ 428.2412 1.0 0.8 0.6 2 0.4 0.2 0.0-0.2 250 300 350 400 Figure S19. UV spectrum of compound 2 17
Transmittance [%] 40 45 50 55 60 65 70 75 2960.92 2875.96 2930.52 2068.66 1698.08 1631.12 1453.66 1383.11 1360.48 1304.16 1262.09 1196.27 1176.96 1144.27 1081.82 1061.09 1019.65 966.84 903.89 802.02 559.09 3432.63 2 4000 3500 3000 2500 2000 1500 Wavenumber cm-1 Figure S20. IR spectrum of compound 2 1000 500 18
3 Figure S21. 1 NMR spectrum of compound 3 (Recorded in methanol-d 4 ) 19
3 Figure S22. 13 C NMR spectrum of compound 3 (Recorded in methanol-d 4 ) 20
3 Figure S23. DEPT spectrum of compound 3 (Recorded in methanol-d 4 ) 21
3 Figure S24. SQC spectrum of compound 3 (Recorded in methanol-d 4 ) 22
3 Figure S25. MBC spectrum of compound 3 (Recorded in methanol-d 4 ) 23
3 Figure S26. 1 1 CSY spectrum of compound 3 (Recorded in methanol-d 4 ) 24
3 Figure S27. NESY spectrum of compound 3 (Recorded in methanol-d 4 ) 25
Intens. x10 4 5 1+ 387.2152 LYY3-24-6.d: +MS, 0.1-0.1min #3-4 4 3 2 1 0 330 340 350 360 370 380 390 400 410 420 m/z Figure S28. RESIMS spectrum of compound 3 382.2611 1+ 403.1889 3 Figure S29. UV spectrum of compound 3 26
3 Transmittance [%] 80 85 90 95 100 3402.81 2965.94 2933.44 2875.78 1703.85 1613.26 1455.41 1382.71 1357.67 1313.21 1268.44 1194.74 1152.76 1093.43 1037.07 973.62 902.83 822.55 639.05 595.63 552.15 4000 3500 3000 2500 2000 1500 Wavenumber cm-1 Figure S30. IR spectrum of compound 3 1000 500 27
4 Figure S31. 1 NMR spectrum of compound 4 (Recorded in methanol-d 4 ) 28
4 Figure S32. 13 C NMR spectrum of compound 4 (Recorded in methanol-d 4 ) 29
4 Figure S33. DEPT spectrum of compound 4 (Recorded in methanol-d 4 ) 30
4 Figure S34. SQC spectrum of compound 4 (Recorded in methanol-d 4 ) 31
4 Figure S35. MBC spectrum of compound 4 (Recorded in methanol-d 4 ) 32
4 Figure S36. 1 1 CSY spectrum of compound 4 (Recorded in methanol-d 4 ) 33
4 Figure S37. NESY spectrum of compound 4 (Recorded in methanol-d 4 ) 34
Figure S38. RESIMS spectrum of compound 4 35
4 Figure S39. UV spectrum of compound 4 36
Transmittance [%] 85 90 95 100 2967.41 2877.42 2932.86 1759.83 1624.70 1588.87 1455.31 1408.30 1359.64 1384.04 1269.17 1189.04 1161.32 1104.15 1031.23 958.91 895.38 838.35 809.81 657.18 581.99 539.35 1702.67 3422.80 4 4000 3500 3000 2500 2000 1500 Wavenumber cm-1 Figure S40. IR spectrum of compound 4 1000 500 37
5 Figure S41. 1 NMR spectrum of compound 5 (Recorded in methanol-d 4 ) 38
5 Figure S42. 13 C NMR spectrum of compound 5 (Recorded in methanol-d 4 ) 39
5 Figure S43. DEPT spectrum of compound 5 (Recorded in methanol-d 4 ) 40
5 Figure S44. SQC spectrum of compound 5 (Recorded in methanol-d 4 ) 41
5 Figure S45. MBC spectrum of compound 5 (Recorded in methanol-d 4 ) 42
5 Figure S46. 1 1 CSY spectrum of compound 5 (Recorded in methanol-d 4 ) 43
5 Figure S47. NESY spectrum of compound 5 (Recorded in methanol-d 4 ) 44
Figure S48. RESIMS spectrum of compound 5 45
5 Figure S49. UV spectrum of compound 5 46
Transmittance [%] 86 88 90 92 94 96 98 100 2930.26 2961.60 2872.76 1745.31 1642.52 1451.67 1383.87 1400.90 1361.60 1305.18 1263.16 1208.25 1162.71 1099.15 1034.79 959.44 931.16 895.49 846.62 823.70 750.01 617.97 501.02 3433.07 5 3500 3000 2500 2000 1500 Wavenumber cm-1 Figure S50. IR spectrum of compound 5 1000 500 47
6 Figure S51. 1 NMR spectrum of compound 6 (Recorded in methanol-d 4 ) 48
6 Figure S52. 13 C NMR spectrum of compound 6 (Recorded in methanol-d 4 ) 49
6 Figure S53. DEPT spectrum of compound 6 (Recorded in methanol-d 4 ) 50
6 Figure S54. SQC spectrum of compound 6 (Recorded in methanol-d 4 ) 51
6 Figure S55. MBC spectrum of compound 6 (Recorded in methanol-d 4 ) 52
6 Figure S56. 1 1 CSY spectrum of compound 6 (Recorded in methanol-d 4 ) 53
6 Figure S57. NESY spectrum of compound 6 (Recorded in methanol-d 4 ) 54
Figure S58. RESIMS spectrum of compound 6 55
6 Figure S59. UV spectrum of compound 6 56
6 3850.56 3864.88 3835.23 3756.61 3671.08 3717.63 3428.99 2956.99 2929.26 2872.32 2895.19 2540.39 1852.99 1785.08 1609.14 1456.59 1383.06 1254.98 1061.41 1096.61 Transmittance [%] 95 96 97 98 99 100 962.10 886.58 671.95 590.53 4000 3500 3000 2500 2000 1500 Wavenumber cm-1 Figure S60. IR spectrum of compound 6 1000 500 57
3 C 7 Figure S61. 1 NMR spectrum of compound 7 (Recorded in methanol-d 4 ) 58
3 C 7 Figure S62. 13 C NMR spectrum of compound 7 (Recorded in methanol-d 4 ) 59
3 C 7 Figure S63. DEPT spectrum of compound 7 (Recorded in methanol-d 4 ) 60
3 C 7 Figure S64. SQC spectrum of compound 7 (Recorded in methanol-d 4 ) 61
3 C 7 Figure S65. MBC spectrum of compound 7 (Recorded in methanol-d 4 ) 62
3 C 7 Figure S66. 1 1 CSY spectrum of compound 7 (Recorded in methanol-d 4 ) 63
3 C 7 Figure S67. NESY spectrum of compound 7 (Recorded in methanol-d 4 ) 64
Intens. x10 4 387.2510 gjk1-50-2.d: +MS, 0.0-0.3min #2-15 2.5 2.0 1.5 1.0 403.2251 0.5 0.0 355.2235 364.2087 376.2608 393.2848 417.2244 360 370 380 390 400 410 420m/z Figure S68. RESIMS spectrum of compound 7 3 C 7 Figure S69. UV spectrum of compound 7 65
3 C 7 Transmittance [%] 3418.14 70 75 80 85 90 95 2958.42 2933.41 2872.75 1730.92 1711.66 1628.89 1452.41 1382.35 1363.87 1339.33 1308.53 1321.77 1249.47 1264.67 1219.05 1194.45 1163.22 1101.11 1074.41 1030.87 1090.27 969.05 944.25 917.58 890.39 910.52 868.37 818.16 807.88 773.29 741.93 705.31 615.52 584.14 556.59 573.94 523.02 541.99 490.30 498.18 450.30 467.27 442.09 410.49 3500 3000 2500 2000 1500 Wavenumber cm-1 Figure S70. IR spectrum of compound 7 1000 500 66
8 Figure S71. 1 NMR spectrum of compound 8 (Recorded in methanol-d 4 ) 67
8 Figure S72. 13 C NMR spectrum of compound 8 (Recorded in methanol-d 4 ) 68
8 Figure S73. DEPT spectrum of compound 8 (Recorded in methanol-d 4 ) 69
8 Figure S74. SQC spectrum of compound 8 (Recorded in methanol-d 4 ) 70
8 Figure S75. MBC spectrum of compound 8 (Recorded in methanol-d 4 ) 71
8 Figure S76. 1 1 CSY spectrum of compound 8 (Recorded in methanol-d 4 ) 72
8 Figure S77. NESY spectrum of compound 8 (Recorded in methanol-d 4 ) 73
8 Figure S78. RESIMS spectrum of compound 8 74
Figure S79. 1 NMR spectrum of the (S)-MTPA ester of 6 in CDCl 3. 75
Figure S80. 1 1 CSY spectrum of the (S)-MTPA ester of 6 in CDCl 3. 76
Figure S81. 1 NMR spectrum of the (R)-MTPA ester of 6 in CDCl 3. 77
Figure S82. 1 1 CSY spectrum of the (R)-MTPA ester of 6 in CDCl 3. 78
Table S1. Experimental and Calculated 13 C NMR Data for three possible structures of 8 (δ in ppm). no. Compound A Compound B Compound C δ C, exptl a δ C, (adj_calcd) b Δδ c δ C, exptl a δ C, (adj_calcd) b Δδ c δ C, exptl a (adj_calcd) b Δδ c 1 127.5 124.2 3.3 127.5 125.9 1.6 127.5 127.0 0.5 2 146.8 151.8-5.0 146.8 156.0-9.2 146.8 152.8-6.0 3 83.5 80.5 3.0 83.5 79.3 4.2 83.5 81.4 2.1 4 35.9 34.7 1.2 35.9 36.4-0.5 35.9 38.2-2.3 5 32.2 23.9 8.3 32.2 29.9 2.3 32.2 31.1 1.1 6 42.9 42.5 0.4 42.9 45.4-2.5 42.9 43.9-1.0 7 45.4 43.0 2.4 45.4 47.8-2.4 45.4 46.7-1.3 8 73.5 68.9 4.6 73.5 69.9 3.6 73.5 73.7-0.2 9 33.0 44.8-11.8 33.0 38.3-5.3 33.0 32.8 0.2 10 72.5 88.6-16.1 72.5 85.0-12.5 72.5 73.0-0.5 11 60.3 63.7-3.4 60.3 62.7-2.4 60.3 61.4-1.1 12 211.0 212.3-1.3 211.0 214.8-3.8 211.0 212.8-1.8 13 38.0 50.7-12.7 38.0 51.7-13.7 38.0 37.4 0.6 14 74.0 83.3-9.3 74.0 79.7-5.7 74.0 73.9 0.1 15 29.7 35.3-5.6 29.7 35.1-5.4 29.7 30.2-0.5 16 77.6 73.2 4.4 77.6 74.7 2.9 77.6 76.0 1.6 17 8.2 5.9 2.3 8.2 7.6 0.6 8.2 11.0-2.8 18 17.8 24.2-6.4 17.8 24.2-6.4 17.8 17.2 0.6 19 20.0 15.6 4.4 20.0 15.5 4.5 20.0 17.2 2.8 20 19.3 15.3 4.0 19.3 14.8 4.5 19.3 16.9 2.4 21 59.6 55.0 4.6 59.6 54.8 4.8 59.6 54.8 4.8 a Recorded in methanol-d 4 at 100 Mz. b Calculated in methanol-d 4. c Δδ = δ exptl δ adj_calcd. 79
13 C NMR Calculation Data C Table S2. Important thermodynamic parameters (a.u.) and boltzmann distribution of the optimized compound C at B3LYP/6-31G(d) level in methanol. Conformation Internal Energy % 1-1195.370421 47.21% 2-1195.370222 38.19% 3-1195.369139 12.17% 4-1195.367604 2.38% Table S3. ptimized coordinates of compound C at B3LYP/6-31G(d) level in methanol. Conformation 1 Atom X Y Z Atom X Y Z C 0.492 1.11 0.386 0.859-1.265-2.717 C 1.071 0.066-0.231 1.281-2.806-1.969 C -1.553 2.292-0.121 3.282-1.823-0.939 C -2.481 1.536-1.064 3.262-1.008-2.502 C 1.288-1.722-1.817-2.394-1.909 1.31 C 2.697-1.153-1.578-2.033-0.911 2.699 80
C -1.698-1.149 1.681-0.579-1.112-0.903 C 0.452-1.281-0.588-0.316-3.117 0.16 C 0.36-2.344 0.552-0.513-2.701 2.46 C -0.315-1.817 1.842 2.419-2.354 1.322 C -0.922 1.314 0.914 2.112-3.567 0.061 C 2.467 0.202-0.86 1.487-3.803 1.694 C -1.901 0.125 0.869-1.901 2.183 2.652 C -2.839 0.278-0.292-0.344 2.931 2.248 C 1.676-3.049 0.921-0.386 1.331 3.029 C -0.883 1.981 2.304-5.25 0.5-1.727 C -5.147-0.354-1.047-5.539-0.061-0.068 C -3.149-1.255-2.314-5.77-1.166-1.437 C 5.851 1.172 0.2-3.197-0.439-3.044 C 3.568 0.534 0.154-3.759-2.078-2.699 C -3.681-0.815-0.94-2.112-1.605-2.266-1.311 3.479-0.171 6.708 1.29-0.468-3.249 0.648 1.048 6.104 0.449 0.988 0.572-1.034 2.653 5.622 2.14 0.671 2.402 1.285-1.805 3.686-0.272 0.894 4.765 0.713-0.591 3.317 1.46 0.693 1.08 2.024 0.466-3.662-1.685-0.273-3.351 2.15-1.316 0.945-0.338 2.087-1.946 1.317-1.997 3.333 1.477-2.022 Conformation 2 Atom X Y Z Atom X Y Z C 0.702-1.067-0.471 1.331 1.068 2.877 C 1.234-0.088 0.272 1.531 2.675 2.17 81
C -1.257-2.455-0.071 3.372 1.852 0.734 C -2.294-1.878 0.885 3.696 1.036 2.265 C 1.58 1.603 1.954-0.951 1.017-2.403 C 2.961 1.147 1.464-2.597 1.388-1.935 C -1.617 1.111-1.537-0.372 0.931 1.292 C 0.592 1.178 0.834 0.407 3.253 0.356 C 0.314 2.313-0.209-1.784 2.322 0.236 C -1.161 2.294-0.67 0.972 3.193-2.072 C -0.697-1.338-0.999 2.306 2.648-1.048 C 2.686-0.206 0.788 1.35 1.467-1.952 C -1.781-0.252-0.882-0.084-1.134-3.089 C -2.756-0.603 0.197-0.009-2.791-2.46 C 1.295 2.403-1.388-1.581-2.069-2.855 C -0.588-1.863-2.447-4.03 1.459 2.71 C -3.319 0.734 2.298-3.306-0.132 2.969 C -5.15-0.295 0.884-2.325 1.193 2.323 C 6.002-0.779-0.729-5.179-1.199 1.504 C 3.699-0.55-0.307-5.464-0.565-0.129 C -3.745 0.337 0.875-5.879 0.412 1.293-0.892-3.613-0.099 5.979-0.068-1.57-3.056-0.893-1.189 6.971-0.705-0.227-1.457 3.448-1.47 5.886-1.796-1.134 2.738-1.189 1.844 3.593 0.156-1.146 5.007-0.483 0.233 3.508-1.561-0.704 1.36-1.899-0.73-3.799 1.245 0.263-1.815-1.677 1.853-1.192 4.231-0.96-3.1-2.598 1.055 2.276-1.981 1.523 82
Conformation 3 Atom X Y Z Atom X Y Z C 0.476 1.281-0.199 0.762-1.65-2.764 C 1.068 0.173-0.664 1.39-2.982-1.792 C -1.756 2.139-0.561 3.364-1.632-1.149 C -2.709 1.091-1.126 3.166-1.225-2.856 C 1.314-1.891-1.848-1.84-1.593 1.97 C 2.679-1.184-1.875-1.284-0.252 2.942 C -1.155-0.737 1.966-0.503-1.263-0.842 C 0.569-1.268-0.638 0.012-2.902 0.609 C 0.726-2.071 0.701 0.272-2.037 2.771 C 0.286-1.294 1.962 2.893-1.966 1.07 C -0.842 1.5 0.521 2.384-3.399 0.156 C 2.373 0.274-1.469 2.062-3.297 1.886 C -1.654 0.262 0.934-1.583 2.654 2.213 C -2.779 0.039-0.032-0.255 3.43 1.329 C 2.103-2.712 0.96 0.083 2.053 2.407 C -0.635 2.473 1.698-5.408-0.292-0.974 C -5.083-0.945-0.154-5.333-0.455 0.792 C -3.24-1.962-1.558-5.657-1.875-0.223 C 4.677 0.897 1.378-3.505-1.35-2.428 C 3.505 0.952-0.682-3.812-2.894-1.625 C -3.574-1.245-0.24-2.179-2.22-1.636-1.693 3.298-0.916 4.667 0.377 2.338-3.013 0.697 1.239 4.521 1.972 1.546 1.239-0.316 2.395 5.654 0.754 0.896 2.088 1.089-2.622 3.276 2.023-0.572 3.631 0.341 0.593 4.453 0.868-1.239 83
0.982 2.227-0.394-3.329-1.922 0.587-3.679 1.542-1.358 1.737 0.021 1.629-2.292 0.694-2.061 2.879 1.076-3.188 Conformation 4 Atom X Y Z Atom X Y Z C 0.902-0.997-0.15 0.987 1.479 2.941 C 1.307 0.117 0.475 1.138 3.041 2.138 C -1.011-2.449 0.256 3.204 2.335 1.018 C -2.162-1.829 1.041 3.408 1.608 2.615 C 1.308 1.967 2.012-2.393 1.021-2.187 C 2.773 1.615 1.724-0.689 0.737-2.463 C -1.435 0.885-1.674-0.483 1.082 1.184 C 0.509 1.371 0.823 0.257 3.382 0.104 C 0.279 2.382-0.35-1.846 2.316-0.106 C -1.134 2.209-0.938 1.513 1.423-1.894 C -0.429-1.417-0.751 2.326 2.732-1.027 C 2.725 0.202 1.089 1.085 3.112-2.225 C -1.578-0.399-0.868-1.094-2.425-2.57 C -2.629-0.682 0.159 0.473-2.987-1.952 C 1.365 2.407-1.437 0.366-1.428-2.79 C -0.156-2.106-2.107-5.129-1.275 1.319 C -5.091-0.454 0.592-5.292-0.867-0.401 C -3.461 0.859 2.018-5.894 0.248 0.842 C 5.007-1.421-1.355-3.461 0.082 2.791 C 3.898 0.036 0.117-4.246 1.578 2.272 C -3.729 0.264 0.626-2.501 1.384 2.068-0.587-3.576 0.404 4.962-2.447-1.731 84
-2.782-1.157-1.2 5.981-1.26-0.867-1.321 3.298-1.851 4.925-0.724-2.202 2.907-0.82 2.088 4.831 0.234 0.672 3.937-1.263-0.441 3.818 0.792-0.678 1.639-1.792-0.235-3.778 1.087-0.098-2.94-2.575 1.232-2.237 3.262-2.17-1.789-1.479 2.013 2.072-0.899 2.577 85