Supporting Information
Alum as an efficient catalysis for the multicomponent synthesis of highly functionalized piperidines
RamneetKaur, Annah Gupta and Kamal K. Kapoor*
Department of Chemistry, University of Jammu, Jammu-180 006, India
*E-mail:
1H and 13C NMR spectra’s
1H NMR spectrum of ethyl 1-phenyl-4-(phenylamino)-2,6-di-p-tolyl-1,2,5,6-tetrahydropyridine-3-carboxylate(4a) in CDCl3
13C NMR spectrum of ethyl 1-phenyl-4-(phenylamino)-2,6-di-p-tolyl-1,2,5,6-tetrahydropyridine-3-carboxylate(4a) in CDCl3
1H NMR spectrum of ethyl-2,6-bis(4-methoxyphenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate(4b) in CDCl3
13CNMR spectrum of ethyl-2,6-bis(4-methoxyphenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (4b) in CDCl3
1H NMR spectrum of ethyl-2,6-bis(4-chlorophenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (4c) in CDCl3
13C NMR spectrum of ethyl-2,6-bis(4-chlorophenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (4c) in CDCl3
1H NMR spectrum of ethyl-2,6-bis(4-bromophenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (4d) in CDCl3
13C NMR spectrum of ethyl-2,6-bis(4-bromophenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (4d) in CDCl3
1H NMR spectrum of ethyl-1,2,6-triphenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (4e) in CDCl3
13C NMR spectrum of ethyl-1,2,6-triphenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (4e) in CDCl3
1H NMR spectrum of ethyl-2,6-bis(4-nitrophenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (4f) in CDCl3
13C NMR spectrum of ethyl-2,6-bis(4-nitrophenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (4f) in CDCl3
1H NMR spectrum of ethyl-2,6-bis(3-methoxyphenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (4g) in CDCl3
13C NMR spectrum of ethyl-2,6-bis(3-methoxyphenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (4g) in CDCl3
1H NMR spectrum of ethyl-2,6-bis(3-nitrophenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (4h) inCDCl3
13C NMR spectrum of ethyl-2,6-bis(3-nitrophenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (4h) in CDCl3
1H NMR spectrum of ethyl-2,6-bis(2-nitrophenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (4i) in CDCl3
13C NMR spectrum of ethyl-2,6-bis(2-nitrophenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (4i) in CDCl3
1H NMR of ethyl-1-phenyl-4-(phenylamino)-2,6-bis(3,4,5-trimethylphenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate (4j) in CDCl3
13C NMR of ethyl-1-phenyl-4-(phenylamino)-2,6-bis(3,4,5-trimethylphenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate (4j) in CDCl3
1H NMR of ethyl-2,6-bis(benzo[d][1,3]dioxol-5-yl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (4k) in CDCl3
13C NMR of ethyl-1-phenyl-4-(phenylamino)-2,6-bis(3,4,5-trimethylphenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate (4k) in CDCl3
1H NMR of ethyl-1-phenyl-4-(phenylamino)-2,6-di(thiophen-2-yl)-1,2,5,6-tetrahydropyridine-3-carboxylate (4l) in CDCl3
13C NMR of ethyl-1-phenyl-4-(phenylamino)-2,6-di(thiophen-2-yl)-1,2,5,6-tetrahydropyridine-3-carboxylate (4l) in CDCl3
1H NMR of ethyl-2,6-diphenyl-1-(p-tolyl)-4-(p-tolylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (4m) in CDCl3
13C NMR of ethyl-2,6-diphenyl-1-(p-tolyl)-4-(p-tolylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (4m) in CDCl3
1H NMR of ethyl-1-(4-fluorophenyl)-4-((4-fluorophenyl)amino)-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-carboxylate (4n) in CDCl3
13C NMR of ethyl-1-(4-fluorophenyl)-4-((4-fluorophenyl)amino)-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-carboxylate (4n) in CDCl3
1H NMR of ethyl-1-(4-chlorophenyl)-4-((4-chlorophenyl)amino)-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-carboxylate (4o)in CDCl3
13C NMR of ethyl-1-(4-chlorophenyl)-4-((4-chlorophenyl)amino)-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-carboxylate (4o)in CDCl3
1H NMR of ethyl-1-(3-chlorophenyl)-4-((3-chlorophenyl)amino)-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-carboxylate (4p) in CDCl3
13C NMR of ethyl-1-(3-chlorophenyl)-4-((3-chlorophenyl)amino)-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-carboxylate (4p) in CDCl3
1H NMR of ethyl-1-(2-chlorophenyl)-4-((2-chlorophenyl)amino)-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-carboxylate (4q) in CDCl3.
13C NMR of ethyl-1-(2-chlorophenyl)-4-((2-chlorophenyl)amino)-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-carboxylate (4q) in CDCl3.
1H NMR of ethyl-1-(4-methoxyphenyl)-4-((4-methoxyphenyl)amino)-2,6-di-p-tolyl-1,2,5,6-tetrahydropyridine-3-carboxylate (4r) in CDCl3
13C NMR of ethyl-1-(4-methoxyphenyl)-4-((4-methoxyphenyl)amino)-2,6-di-p-tolyl-1,2,5,6-tetrahydropyridine-3-carboxylate in (4r) CDCl3
1H NMR of methyl-1,2,6-triphenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (4s) in CDCl3
13C NMR of methyl-1,2,6-triphenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (4s) in CDCl3
1H NMR of methyl 2,6-bis(4-methoxyphenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate in (4t) CDCl3
13C NMR of methyl 2,6-bis(4-methoxyphenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (4t ) in CDCl3
1H NMR of methyl-2,6-bis(4-bromophenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (4u ) in CDCl3
13C NMR of methyl-2,6-bis(4-bromophenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (4u ) in CDCl3
1H NMR of methyl 1-(4-chlorophenyl)-4-((4-chlorophenyl)amino)-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-carboxylate (4v) in CDCl3
13C NMR of methyl 1-(4-chlorophenyl)-4-((4-chlorophenyl)amino)-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-carboxylate (4v) in CDCl3
1H NMR of methyl 2,6-bis(benzo[d][1,3]dioxol-5-yl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (4w) in CDCl3
13C NMR of methyl 2,6-bis(benzo[d][1,3]dioxol-5-yl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (4w) in CDCl3
1H NMR of (Z)-Ethyl 3-(Phenylamino)but-2-enoate (I) in CDCl3
13C NMR of (Z)-Ethyl 3-(Phenylamino)but-2-enoate (I) in CDCl3
Table 1: Crystal data and structure refinement for ethyl 1-phenyl-4-(phenylamino)-2,6-bis(3,4,5-trimethoxyphenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate.Empirical formula / C38H42N2O8
Formula weight / 653.73
Temperature/K / 293(2)
Crystal system / monoclinic
Space group / P21/c
a/Å / 17.8058(14)
b/Å / 10.7940(7)
c/Å / 19.6612(15)
α/° / 90.00
β/° / 112.962(9)
γ/° / 90.00
Volume/Å3 / 3479.4(4)
Z / 4
ρcalcg/cm3 / 1.248
μ/mm1 / 0.088
F(000) / 1388.0
Crystal size/mm3 / 0.281 × 0.172 × 0.085
Radiation / MoKα (λ = 0.71073)
2Θ range for data collection/° / 4.2 to 56.64
Index ranges / -23 ≤ h ≤ 22, -10 ≤ k ≤ 13, -26 ≤ l ≤ 15
Reflections collected / 11822
Independent reflections / 7532 [Rint= 0.0327, Rsigma= 0.0552]
Data/restraints/parameters / 7532/0/440
Goodness-of-fit on F2 / 1.077
Final R indexes [I>=2σ (I)] / R1= 0.0869, wR2= 0.2421
Final R indexes [all data] / R1= 0.1337, wR2= 0.2735
Largest diff. peak/hole / e Å-3 / 0.82/-0.47
ORTEPof ethyl 1-phenyl-4-(phenylamino)-2,6-bis(3,4,5-trimethoxyphenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate (4k), showing the atom labeling scheme.
ccdc no: 1469233
Table 2: Fractional Atomic Coordinates (×104) and Equivalent Isotropic Displacement Parameters (Å2×103) for 4k. Ueqis defined as 1/3 of of the trace of the orthogonalisedUIJtensor.
Atom / x / Y / z / U(eq)
N1 / 2501.9(17) / 3799(3) / 576.2(17) / 46.3(7)
C2 / 2112(2) / 2772(3) / 801.2(19) / 44.3(8)
C13 / 3925(2) / 3664(3) / 587.9(19) / 44.1(8)
O21 / 6098.9(16) / 3964(3) / 912.0(18) / 74.0(9)
N36 / 4076.0(19) / 1101(3) / 1826.1(19) / 58.4(8)
O23 / 5593.3(18) / 2481(3) / -272.4(16) / 76.8(9)
O44 / 1665.4(18) / 330(3) / 369.4(17) / 72.0(8)
C6 / 3368(2) / 4017(3) / 986.6(19) / 43.9(8)
C4 / 3477(2) / 1958(3) / 1550.3(19) / 45.1(8)
C3 / 2699(2) / 1693(3) / 1070.5(18) / 43.4(8)
C25 / 1760.0(19) / 3122(3) / 1374.6(19) / 45.0(8)
C7 / 2030(2) / 4654(3) / 53.2(19) / 45.9(8)
O46 / 2907.6(19) / -448(3) / 1005(2) / 78.6(9)
C5 / 3656(2) / 3305(3) / 1712.9(19) / 47.2(8)
C17 / 5285(2) / 3660(4) / 622(2) / 54.0(9)
C14 / 3669(2) / 2908(4) / -28(2) / 50.8(9)
O19 / 4047.5(19) / 1796(3) / -926.4(16) / 81.5(10)
C18 / 4728(2) / 4068(4) / 902(2) / 50.8(9)
C8 / 1173(2) / 4658(4) / -210(2) / 54.2(9)
C15 / 4231(2) / 2531(4) / -315(2) / 56.3(10)
C37 / 4917(2) / 1363(3) / 2212(2) / 50.9(9)
C16 / 5041(2) / 2874(4) / 18(2) / 56.6(10)
C38 / 5202(3) / 1934(4) / 2899(2) / 58.9(10)
C43 / 2460(2) / 458(4) / 827(2) / 54.4(9)
C40 / 6550(3) / 1934(4) / 2929(3) / 67.8(11)
C26 / 1797(2) / 4293(4) / 1653(2) / 56.5(10)
C12 / 2400(2) / 5554(3) / -230(2) / 55.1(9)
C42 / 5459(3) / 1048(4) / 1900(2) / 64.0(11)
C30 / 1391(2) / 2190(4) / 1622(2) / 62.0(11)
C11 / 1923(3) / 6388(4) / -755(2) / 65.5(11)
C29 / 1078(2) / 2434(5) / 2148(2) / 74.1(13)
C10 / 1084(3) / 6381(4) / -1009(2) / 70.2(12)
O35 / 696(3) / 1565(6) / 2402(3) / 124.2(16)
C27 / 1499(3) / 4533(5) / 2197(2) / 75.3(13)
C41 / 6277(3) / 1340(5) / 2260(3) / 74.1(13)
C39 / 6012(3) / 2226(4) / 3247(2) / 64.8(11)
C9 / 718(3) / 5514(4) / -736(2) / 63.3(11)
C22 / 6390(3) / 4726(5) / 1539(3) / 84.0(15)
O33 / 799(3) / 3851(5) / 2953(2) / 129.3(18)
C28 / 1131(3) / 3601(6) / 2443(2) / 80.3(16)
O31 / 1621(3) / 5703(5) / 2517(3) / 139.6(19)
C20 / 3230(3) / 1532(6) / -1336(3) / 95.1(17)
C24 / 6003(3) / 1377(6) / 62(3) / 94.6(18)
C45 / 1390(4) / -906(5) / 89(4) / 108(2)
C34 / 1144(4) / 3290(9) / 3649(3) / 150(3)
C0AA / 1096(5) / 6565(7) / 2236(5) / 159(3)
C1 / 821(5) / 297(9) / 2279(5) / 152(3)
C1AA / 979(8) / -1470(8) / 458(7) / 232(7)
Table 3: Anisotropic Displacement Parameters (Å2×103) for 4k. The Anisotropic displacement factor exponent takes the form: -2π2[h2a*2U11+2hka*b*U12+…].
Atom / U11 / U22 / U33 / U23 / U13 / U12
N1 / 36.8(15) / 45.5(16) / 61.7(17) / 7.2(14) / 25.0(14) / 0.5(13)
C2 / 42.5(18) / 42.6(19) / 53.9(19) / -3.9(15) / 25.6(16) / -4.0(15)
C13 / 38.3(18) / 46.5(19) / 52.7(19) / 3.0(16) / 23.5(15) / 0.7(15)
O21 / 42.2(15) / 104(2) / 85(2) / -2.7(18) / 34.5(15) / -10.2(16)
N36 / 48.8(19) / 47.6(18) / 75(2) / 0.9(16) / 20.7(16) / 6.0(15)
O23 / 67.3(19) / 114(3) / 69.6(18) / 9.5(18) / 48.4(16) / 20.1(18)
O44 / 65.1(19) / 50.7(17) / 86(2) / -17.2(15) / 14.1(16) / -6.3(14)
C6 / 37.8(18) / 42.7(19) / 54.3(19) / -3.0(15) / 21.4(15) / -1.5(14)
C4 / 49(2) / 48(2) / 48.1(18) / 2.2(16) / 29.7(16) / 5.2(16)
C3 / 44.5(19) / 45.0(19) / 47.8(18) / -1.4(15) / 25.8(16) / 1.5(15)
C25 / 31.7(17) / 54(2) / 50.3(19) / -4.0(16) / 17.2(15) / 1.4(15)
C7 / 48(2) / 44.3(19) / 49.9(19) / -2.7(15) / 23.6(16) / 4.5(15)
O46 / 73(2) / 47.3(17) / 110(2) / -11.1(16) / 30.7(18) / 6.0(15)
C5 / 41.9(19) / 52(2) / 52.7(19) / -6.3(16) / 23.9(16) / 1.2(16)
C17 / 42(2) / 67(2) / 59(2) / 11.4(19) / 26.5(18) / -2.1(18)
C14 / 44(2) / 61(2) / 50.5(19) / -2.0(17) / 21.8(16) / 0.0(17)
O19 / 65.5(19) / 117(3) / 62.5(17) / -29.1(18) / 25.6(15) / 6.9(18)
C18 / 44(2) / 55(2) / 59(2) / -2.6(17) / 26.2(17) / -4.0(16)
C8 / 44(2) / 59(2) / 60(2) / -1.2(19) / 20.5(18) / -2.0(18)
C15 / 56(2) / 69(3) / 50(2) / -1.0(19) / 27.0(18) / 7(2)
C37 / 46(2) / 53(2) / 54(2) / 9.9(17) / 19.8(17) / 9.9(17)
C16 / 51(2) / 74(3) / 55(2) / 11(2) / 32.2(18) / 9.6(19)
C38 / 62(2) / 68(3) / 51(2) / 6.2(19) / 26.7(19) / 5(2)
C43 / 58(2) / 48(2) / 64(2) / -3.8(18) / 32(2) / 2.7(18)
C40 / 48(2) / 69(3) / 78(3) / 6(2) / 17(2) / -2(2)
C26 / 51(2) / 59(2) / 59(2) / -4.2(19) / 20.9(18) / 9.8(18)
C12 / 54(2) / 48(2) / 69(2) / 5.3(19) / 29.5(19) / 0.7(18)
C42 / 62(3) / 70(3) / 62(2) / -1(2) / 26(2) / 13(2)
C30 / 54(2) / 72(3) / 74(3) / -3(2) / 40(2) / -9(2)
C11 / 72(3) / 57(2) / 71(3) / 11(2) / 32(2) / 2(2)
C29 / 45(2) / 119(4) / 68(3) / 9(3) / 33(2) / 0(2)
C10 / 69(3) / 65(3) / 67(3) / 14(2) / 15(2) / 13(2)
O35 / 108(3) / 178(5) / 126(3) / 15(3) / 89(3) / -30(3)
C27 / 71(3) / 93(4) / 59(2) / -13(2) / 23(2) / 30(3)
C41 / 56(3) / 84(3) / 90(3) / 6(3) / 37(2) / 12(2)
C39 / 64(3) / 65(3) / 59(2) / 1(2) / 18(2) / -4(2)
C9 / 49(2) / 72(3) / 62(2) / 3(2) / 14.3(19) / 7(2)
C22 / 51(3) / 103(4) / 93(3) / -10(3) / 23(2) / -20(3)
O33 / 115(3) / 220(5) / 79(2) / 21(3) / 66(2) / 81(3)
C28 / 46(2) / 144(5) / 56(2) / -2(3) / 26(2) / 30(3)
O31 / 165(5) / 125(4) / 118(3) / -51(3) / 44(3) / 47(3)
C20 / 81(4) / 116(5) / 80(3) / -42(3) / 22(3) / -5(3)
C24 / 85(4) / 120(5) / 99(4) / 11(3) / 59(3) / 37(3)
C45 / 114(5) / 63(3) / 143(5) / -42(3) / 45(4) / -31(3)
C34 / 119(5) / 284(11) / 65(3) / 18(5) / 55(4) / 51(6)
C0AA / 158(8) / 74(5) / 224(10) / -8(5) / 53(7) / 4(5)
C1 / 149(7) / 165(8) / 172(8) / 45(7) / 95(6) / -47(6)
C1AA / 331(16) / 134(7) / 331(15) / -120(9) / 237(14) / -138(9)
Table 4: Bond Lengths for 4k.
Atom / Atom / Length/Å / Atom / Atom / Length/Å
N1 / C2 / 1.466(4) / C17 / C16 / 1.384(6)
N1 / C6 / 1.454(4) / C14 / C15 / 1.389(5)
N1 / C7 / 1.393(4) / O19 / C15 / 1.369(5)
C2 / C3 / 1.516(5) / O19 / C20 / 1.391(6)
C2 / C25 / 1.535(4) / C8 / C9 / 1.388(6)
C13 / C6 / 1.533(4) / C15 / C16 / 1.382(5)
C13 / C14 / 1.381(5) / C37 / C38 / 1.388(5)
C13 / C18 / 1.388(5) / C37 / C42 / 1.374(5)
O21 / C17 / 1.374(4) / C38 / C39 / 1.371(6)
O21 / C22 / 1.403(6) / C40 / C41 / 1.370(6)
N36 / C4 / 1.356(4) / C40 / C39 / 1.369(6)
N36 / C37 / 1.419(5) / C26 / C27 / 1.392(6)
O23 / C16 / 1.382(4) / C12 / C11 / 1.384(6)
O23 / C24 / 1.418(6) / C42 / C41 / 1.384(6)
O44 / C43 / 1.356(5) / C30 / C29 / 1.378(5)
O44 / C45 / 1.454(6) / C11 / C10 / 1.378(6)
C6 / C5 / 1.524(5) / C29 / O35 / 1.363(6)
C4 / C3 / 1.368(5) / C29 / C28 / 1.375(7)
C4 / C5 / 1.496(5) / C10 / C9 / 1.365(6)
C3 / C43 / 1.424(5) / O35 / C1 / 1.423(9)
C25 / C26 / 1.369(5) / C27 / C28 / 1.387(7)
C25 / C30 / 1.389(5) / C27 / O31 / 1.390(6)
C7 / C8 / 1.407(5) / O33 / C28 / 1.375(5)
C7 / C12 / 1.406(5) / O33 / C34 / 1.400(7)
O46 / C43 / 1.223(5) / O31 / C0AA / 1.280(8)
C17 / C18 / 1.382(5) / C45 / C1AA / 1.359(10)
Table 5: Bond Angles for 4k.
Atom / Atom / Atom / Angle/˚ / Atom / Atom / Atom / Angle/˚
C6 / N1 / C2 / 118.7(3) / O19 / C15 / C14 / 124.3(4)
C7 / N1 / C2 / 120.2(3) / O19 / C15 / C16 / 114.8(3)
C7 / N1 / C6 / 120.4(3) / C16 / C15 / C14 / 120.9(4)
N1 / C2 / C3 / 110.1(3) / C38 / C37 / N36 / 121.1(3)
N1 / C2 / C25 / 114.4(3) / C42 / C37 / N36 / 119.4(4)
C3 / C2 / C25 / 110.9(3) / C42 / C37 / C38 / 119.5(4)
C14 / C13 / C6 / 122.5(3) / O23 / C16 / C17 / 120.5(4)
C14 / C13 / C18 / 120.4(3) / C15 / C16 / O23 / 120.0(4)
C18 / C13 / C6 / 117.0(3) / C15 / C16 / C17 / 119.4(3)
C17 / O21 / C22 / 118.3(3) / C39 / C38 / C37 / 120.0(4)
C4 / N36 / C37 / 125.4(3) / O44 / C43 / C3 / 114.6(3)
C16 / O23 / C24 / 112.7(3) / O46 / C43 / O44 / 120.2(4)
C43 / O44 / C45 / 117.1(4) / O46 / C43 / C3 / 125.2(4)
N1 / C6 / C13 / 115.7(3) / C39 / C40 / C41 / 119.7(4)
N1 / C6 / C5 / 109.5(3) / C25 / C26 / C27 / 120.4(4)
C5 / C6 / C13 / 107.8(3) / C11 / C12 / C7 / 119.9(4)
N36 / C4 / C3 / 124.1(3) / C37 / C42 / C41 / 119.8(4)
N36 / C4 / C5 / 120.6(3) / C29 / C30 / C25 / 120.6(4)
C3 / C4 / C5 / 115.1(3) / C10 / C11 / C12 / 122.0(4)
C4 / C3 / C2 / 117.1(3) / O35 / C29 / C30 / 123.3(5)
C4 / C3 / C43 / 121.1(3) / O35 / C29 / C28 / 116.0(4)
C43 / C3 / C2 / 121.8(3) / C28 / C29 / C30 / 120.7(4)
C26 / C25 / C2 / 123.4(3) / C9 / C10 / C11 / 118.6(4)
C26 / C25 / C30 / 119.0(3) / C29 / O35 / C1 / 117.8(5)
C30 / C25 / C2 / 117.6(3) / C28 / C27 / C26 / 120.4(4)
N1 / C7 / C8 / 121.9(3) / C28 / C27 / O31 / 120.9(5)
N1 / C7 / C12 / 120.6(3) / O31 / C27 / C26 / 118.6(5)
C12 / C7 / C8 / 117.5(3) / C40 / C41 / C42 / 120.5(4)
C4 / C5 / C6 / 108.9(3) / C40 / C39 / C38 / 120.5(4)
O21 / C17 / C18 / 124.3(4) / C10 / C9 / C8 / 121.3(4)
O21 / C17 / C16 / 115.5(3) / C28 / O33 / C34 / 118.6(4)
C18 / C17 / C16 / 120.2(3) / C29 / C28 / C27 / 118.8(4)
C13 / C14 / C15 / 119.1(3) / C29 / C28 / O33 / 120.6(5)
C15 / O19 / C20 / 117.7(3) / O33 / C28 / C27 / 120.5(6)
C17 / C18 / C13 / 119.8(3) / C0AA / O31 / C27 / 120.4(6)
C9 / C8 / C7 / 120.7(4) / C1AA / C45 / O44 / 112.3(6)
Table 6: Hydrogen Bonds for 4k.
D / H / A / d(D-H)/Å / d(H-A)/Å / d(D-A)/Å / D-H-A/°
N36 / H36 / O46 / 0.86 / 2.04 / 2.666(5) / 129.4
C12 / H12 / O211 / 0.93 / 2.82 / 3.465(4) / 127.4
C30 / H30 / O44 / 0.93 / 2.62 / 3.358(5) / 136.3
C39 / H39 / O232 / 0.93 / 2.63 / 3.291(5) / 128.2
C39 / H39 / O463 / 0.93 / 2.55 / 3.155(5) / 123.5
C1 / H1B / O334 / 0.96 / 2.50 / 3.152(8) / 125.5
11-X,1-Y,-Z;2+X,1/2-Y,1/2+Z;31-X,1/2+Y,1/2-Z;4-X,-1/2+Y,1/2-Z
Table 7: Hydrogen Atom Coordinates (Å×104) and Isotropic Displacement Parameters (Å2×103) for 4k.Atom / x / y / z / U(eq)
H2 / 1654 / 2490 / 358 / 53
H36 / 3935 / 334 / 1762 / 70
H6 / 3443 / 4903 / 1104 / 53
H5A / 4237 / 3426 / 1982 / 57
H5B / 3376 / 3608 / 2016 / 57
H14 / 3128 / 2654 / -246 / 61
H18 / 4890 / 4612 / 1301 / 61
H8 / 909 / 4080 / -30 / 65
H38 / 4842 / 2119 / 3123 / 71
H40 / 7099 / 2139 / 3166 / 81
H26 / 2022 / 4933 / 1476 / 68
H12 / 2966 / 5589 / -64 / 66
H42 / 5277 / 641 / 1447 / 77
H30 / 1355 / 1394 / 1431 / 74
H11 / 2177 / 6971 / -943 / 79
H10 / 774 / 6954 / -1360 / 84
H41 / 6643 / 1130 / 2048 / 89
H39 / 6198 / 2624 / 3702 / 78
H9 / 152 / 5497 / -905 / 76
H22A / 6105 / 5503 / 1430 / 126
H22B / 6963 / 4870 / 1679 / 126
H22C / 6301 / 4327 / 1938 / 126
H20A / 3178 / 1102 / -1779 / 143
H20B / 2925 / 2291 / -1462 / 143
H20C / 3022 / 1022 / -1049 / 143
H24A / 6378 / 1144 / -157 / 142
H24B / 5611 / 726 / -12 / 142
H24C / 6295 / 1512 / 582 / 142
H45 / 1484 / -1270 / -300 / 130
H34A / 1317 / 2466 / 3597 / 225
H34B / 745 / 3254 / 3866 / 225
H34C / 1605 / 3765 / 3961 / 225
H0AA / 1027 / 6700 / 1733 / 238
H0AB / 1284 / 7315 / 2514 / 238
H0AC / 584 / 6326 / 2252 / 238
H1A / 558 / 114 / 1762 / 228
H1B / 594 / -216 / 2550 / 228
H1C / 1395 / 136 / 2443 / 228
H1AA / 410 / -1268 / 226 / 348
H1AB / 1190 / -1189 / 961 / 348
H1AC / 1047 / -2351 / 448 / 348