Supporting Information

One-Pot, Three-Component Assembly of Indoloquinolines: Total Synthesis of Isocryptolepine Alexander V. Aksenov,* Dmitrii A. Aksenov, Naila A. Orazova, Nicolai A. Aksenov, Georgii D. Griaznov, Annelise De Carvalho, Robert Kiss, Véronique Mathieu, Alexander Kornienko, and Michael Rubin* Supporting Information Table of Content Crystal Structure Data...S 2 Spectral Charts... S18

Crystal Structure Data Table S1. Crystal data and structure refinement for compound 1fa. Identification code 1fa Empirical formula C 17 H 14 N 2 O 2 Formula weight 278.30 Temperature/K 100.00(10) Crystal system tetragonal Space group I4 1 cd a/å 20.00573(15) b/å 20.00573(15) c/å 13.20742(18) α/ 90 β/ 90 γ/ 90 Volume/Å 3 5286.00(11) Z 16 ρ calc g/cm 3 1.399 µ/mm -1 0.754 F(000) 2336.0 Crystal size/mm 3 0.263 0.064 0.053 Radiation CuKα (λ = 1.54184) 2Θ range for data collection/ 8.84 to 148.144 Index ranges -23 h 24, -22 k 22, -15 l 14 Reflections collected 11191 Independent reflections 2526 [R int = 0.0293, R sigma = 0.0232] Data/restraints/parameters 2526/1/187 Goodness-of-fit on F 2 1.062 Final R indexes [I>=2σ (I)] R 1 = 0.0346, wr 2 = 0.0869 Final R indexes [all data] R 1 = 0.0369, wr 2 = 0.0878 Largest diff. peak/hole / e Å -3 0.33/-0.32 Flack parameter 0.02(9) S2

Table S2. Fractional Atomic Coordinates ( 10 4 ) and Equivalent Isotropic Displacement Parameters (Å 2 10 3 ) for 1fa. U eq is defined as 1/3 of of the trace of the orthogonalised U IJ tensor. Atom x y z U(eq) C12 3899.8(12) 4421.0(12) 4503.3(19) 12.9(5) C14 4338.8(9) 5700.3(8) 4936.3(9) 13.4(5) C15 4561.3(9) 6303.7(7) 5391.4(11) 13.9(5) C5 4515.8(9) 6227.9(7) 6458.1(11) 14.2(5) N1 4265.1(9) 5577.6(7) 6662.4(9) 14.3(4) C6 4155.7(9) 5251.6(6) 5721.9(12) 13.5(5) C7 3922.6(12) 4612.9(12) 5539.5(18) 14.5(5) N2 4090.5(10) 4837.3(10) 3720.7(15) 14.7(4) C9 3501.5(12) 3528.0(12) 6040(2) 15.1(5) C8 3708.7(12) 4159.3(12) 6299.1(19) 14.4(5) C3 4956.3(14) 7302.6(13) 6755(2) 19.8(5) C4 4714.4(13) 6701.4(13) 7140(2) 17.1(5) C13 4300.4(11) 5447.1(12) 3949.2(19) 13.3(5) C10 3504.7(12) 3324.2(12) 5004(2) 15.1(5) C1 4790.4(12) 6927.5(12) 5024(2) 17.0(5) C11 3677.2(12) 3767.7(13) 4258(2) 14.9(5) C2 4986.8(13) 7413.8(12) 5707(2) 19.6(5) O1 3280.9(9) 3051.6(9) 6699.3(14) 18.9(4) O2 3325.6(9) 2674.9(9) 4850.7(14) 18.3(4) C16 3394.2(14) 2417.4(13) 3848(2) 22.3(6) C17 3284.6(15) 3226.3(13) 7749(2) 21.3(6) S3

Table S3. Anisotropic Displacement Parameters (Å 2 10 3 ) for 1fa. The Anisotropic displacement factor exponent takes the form: -2π 2 [h 2 a* 2 U 11 +2hka*b*U 12 + ]. Atom U 11 U 22 U 33 U 23 U 13 U 12 C12 11.3(11) 13.1(11) 14.3(13) -0.6(9) -1.2(9) 1.2(8) C14 13.3(11) 13.4(11) 13.5(12) 0.6(9) -0.4(9) 1.1(8) C15 13.9(11) 15.4(12) 12.5(12) -1.0(9) 0.3(9) 1.0(9) C5 14.5(11) 13.5(11) 14.8(13) 0.8(9) 0.4(9) -2.1(8) N1 19.2(10) 12.2(10) 11.4(11) 0.3(8) -0.7(8) -3.3(7) C6 12.6(11) 15.3(11) 12.7(12) -0.8(9) -1.5(9) 0.9(9) C7 13.5(11) 15.8(12) 14.1(14) -0.1(9) -0.6(9) 2.2(9) N2 16(1) 16.9(10) 11.1(11) -0.3(7) 0.2(8) 2.2(7) C9 13.1(11) 15.1(12) 16.9(13) 2.3(9) -0.7(8) -0.4(9) C8 14.5(11) 15.8(11) 12.8(13) -1.0(9) -1.3(8) 1.0(9) C3 23.0(12) 14.8(11) 21.6(14) -4.4(10) -0.7(10) -2.8(10) C4 19.8(12) 18.0(12) 13.6(12) -1.7(9) 0.7(10) -1.1(10) C13 14.2(11) 14.2(11) 11.6(12) 1.9(9) 0.2(9) 0.1(8) C10 13.2(11) 13.4(11) 18.8(14) -2.8(9) -1.6(9) -0.1(8) C1 20.3(12) 15.6(12) 15.2(12) 2.3(10) 2.7(9) 0.4(9) C11 13.8(11) 17.2(12) 13.7(12) -2.2(9) -0.4(9) 1.5(9) C2 21.2(12) 13.7(11) 23.9(13) 0.4(10) 4.4(11) -1.7(10) O1 25.0(9) 15.8(9) 15.9(10) 2.8(7) 0.6(7) -5.4(7) O2 22.1(9) 12.7(8) 20.1(10) -2.3(7) 0.0(7) -2.8(6) C16 27.2(13) 15.8(12) 23.8(15) -4.4(10) -2.3(11) -0.6(10) C17 30.1(15) 18.6(13) 15.3(14) 0.6(10) 2.8(10) -4.7(10) Table S4. Bond Lengths for 1fa. Atom Atom Length/Å Atom Atom Length/Å C12 C7 1.422(3) C7 C8 1.419(3) C12 N2 1.381(3) N2 C13 1.325(3) C12 C11 1.418(3) C9 C8 1.373(3) C14 C15 1.4200 C9 C10 1.427(4) C14 C6 1.4200 C9 O1 1.364(3) C14 C13 1.401(3) C3 C4 1.392(4) C15 C5 1.4200 C3 C2 1.403(4) C15 C1 1.415(3) C10 C11 1.370(4) C5 N1 1.4200 C10 O2 1.363(3) C5 C4 1.366(3) C1 C2 1.384(4) N1 C6 1.4200 O1 C17 1.430(3) C6 C7 1.381(3) O2 C16 1.427(3) S4

Table S5. Bond Angles for 1fa. Atom Atom Atom Angle/ Atom Atom Atom Angle/ N2 C12 C7 123.3(2) C8 C7 C12 119.9(2) N2 C12 C11 118.1(2) C13 N2 C12 118.2(2) C11 C12 C7 118.6(2) C8 C9 C10 120.0(2) C6 C14 C15 108.0 O1 C9 C8 125.5(2) C13 C14 C15 135.93(14) O1 C9 C10 114.4(2) C13 C14 C6 115.93(14) C9 C8 C7 120.2(2) C14 C15 C5 108.0 C4 C3 C2 120.8(2) C1 C15 C14 134.92(15) C5 C4 C3 117.4(2) C1 C15 C5 117.07(15) N2 C13 C14 124.2(2) N1 C5 C15 108.0 C11 C10 C9 120.4(2) C4 C5 C15 124.13(15) O2 C10 C9 114.4(2) C4 C5 N1 127.80(15) O2 C10 C11 125.2(2) C6 N1 C5 108.0 C2 C1 C15 119.2(2) N1 C6 C14 108.0 C10 C11 C12 120.7(2) C7 C6 C14 122.99(15) C1 C2 C3 121.3(2) C7 C6 N1 129.01(15) C9 O1 C17 116.5(2) C6 C7 C12 115.4(2) C10 O2 C16 117.2(2) C6 C7 C8 124.8(2) S5

Table S6. Torsion Angles for 1fa A B C D Angle/ A B C D Angle/ C12 C7 C8 C9 2.2(3) N2 C12 C7 C8 179.1(2) C12 N2 C13 C14-0.3(3) N2 C12 C11 C10 177.6(2) C14 C15 C5 N1 0.0 C9 C10 C11 C12 4.4(4) C14 C15 C5 C4 177.2(2) C9 C10 O2 C16-172.8(2) C14 C15 C1 C2-178.51(18) C8 C9 C10 C11-3.8(4) C14 C6 C7 C12 2.2(3) C8 C9 C10 O2 176.3(2) C14 C6 C7 C8-177.28(18) C8 C9 O1 C17-1.7(4) C15 C14 C6 N1 0.0 C4 C5 N1 C6-177.1(2) C15 C14 C6 C7-179.3(2) C4 C3 C2 C1-1.2(4) C15 C14 C13 N2 177.03(17) C13 C14 C15 C5-175.3(2) C15 C5 N1 C6 0.0 C13 C14 C15 C1 6.2(3) C15 C5 C4 C3 2.1(3) C13 C14 C6 N1 176.38(18) C15 C1 C2 C3-0.7(4) C13 C14 C6 C7-3.0(2) C5 C15 C1 C2 3.1(3) C10 C9 C8 C7 0.4(4) C5 N1 C6 C14 0.0 C10 C9 O1 C17 178.5(2) C5 N1 C6 C7 179.3(2) C1 C15 C5 N1 178.81(19) N1 C5 C4 C3 178.80(18) C1 C15 C5 C4-3.9(2) N1 C6 C7 C12-176.98(16) C11 C12 C7 C6 178.9(2) N1 C6 C7 C8 3.5(3) C11 C12 C7 C8-1.6(3) C6 C14 C15 C5 0.0 C11 C12 N2 C13-179.8(2) C6 C14 C15 C1-178.5(2) C11 C10 O2 C16 7.3(4) C6 C14 C13 N2 2.0(3) C2 C3 C4 C5 0.5(4) C6 C7 C8 C9-178.3(2) O1 C9 C8 C7-179.5(2) C7 C12 N2 C13-0.5(3) O1 C9 C10 C11 176.1(2) C7 C12 C11 C10-1.7(3) O1 C9 C10 O2-3.8(3) N2 C12 C7 C6-0.4(3) O2 C10 C11 C12-175.7(2) S6

Table S7. Hydrogen Atom Coordinates (Å 10 4 ) and Isotropic Displacement Parameters (Å 2 10 3 ) for 1fa Atom x y z U(eq) H8 3709 4290 6975 17 H3 5099 7634 7198 24 H4 4689 6625 7833 21 H13 4431 5725 3420 16 H1A 4809 7010 4332 20 H11 3648 3639 3583 18 H2 5142 7822 5467 24 H16A 3100 2655 3401 33 H16B 3281 1951 3844 33 H16C 3848 2473 3626 33 H17A 3022 3623 7850 32 H17B 3736 3307 7965 32 H17C 3098 2866 8138 32 H1 4155(17) 5396(18) 7320(30) 28(9) Experimental Single crystals of C17H14N2O2 (1fa) were recrystallized from EtOH. A suitable crystal was selected and glued with acrylic glue to the glass stick on a SuperNova, Dual, AtlasS2 diffractometer. The crystal was kept at 100.00(10) K during data collection. The structure was solved with the ShelXD structure solution program 1 using Olex2 interface 2 and refined with the ShelXL [3] refinement package 3 using Least Squares minimization algorithm. Crystal structure determination of 1fa Crystal Data for C17H14N2O2 (M =278.30 g/mol): tetragonal, space group I41cd (no. 110), a = 20.00573(15) Å, c = 13.20742(18) Å, V = 5286.00(11) Å 3, Z = 16, T = 100.00(10) K, μ(cukα) = 0.754 mm -1, Dcalc = 1.399 g/cm 3, 11191 reflections measured (8.84 2Θ 148.144 ), 2526 unique (Rint = 0.0293, Rsigma = 0.0232) which were used in all calculations. The final R1 was 0.0346 (I > 2σ(I)) and wr2 was 0.0878 (all data). (1) Sheldrick, G.M. Acta Cryst. 2008, A64, 112-122. (2) Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. J. Appl. Cryst. 2009, 42, 339-341. (3) Sheldrick, G.M. Acta Cryst. 2015, C71, 3-8. S7

Refinement model description Number of restraints - 1, number of constraints - unknown. Details: 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Aromatic/amide H refined with riding coordinates: C8(H8), C3(H3), C4(H4), C13(H13), C1(H1a), C11(H11), C2(H2) 2.b Fitted pentagon refined as free rotating group: C14(C15,C5,N1,C6) 2.c Idealised Me refined as rotating group: C16(H16a,H16b,H16c), C17(H17a,H17b,H17c) Figure S1. ORTEP drawing of compound 1fa: showing 50% probability amplitude displacement ellipsoids. S8

Figure S2. Packing of molecules (16 units) of compound 1fa in the crystalline lattice view along axis c. S9

Table S8. Crystal data and structure refinement for compound 1ea Identification code 1ea Empirical formula C 16 H 12 N 2 O Formula weight 248.28 Temperature/K 292.96(15) Crystal system monoclinic Space group P2 1 /c a/å 5.1053(3) b/å 18.1238(12) c/å 12.8535(7) α/ 90 β/ 93.383(6) γ/ 90 Volume/Å 3 1187.22(13) Z 4 ρ calc g/cm 3 1.389 µ/mm -1 0.706 F(000) 520.0 Crystal size/mm 3 0.554 0.136 0.097 Radiation CuKα (λ = 1.54184) 2Θ range for data collection/ 8.444 to 147.664 Index ranges -5 h 6, -22 k 15, -15 l 15 Reflections collected 7012 Independent reflections 2319 [R int = 0.0304, R sigma = 0.0305] Data/restraints/parameters 2319/0/177 Goodness-of-fit on F 2 1.088 Final R indexes [I>=2σ (I)] R 1 = 0.0460, wr 2 = 0.1237 Final R indexes [all data] R 1 = 0.0527, wr 2 = 0.1333 Largest diff. peak/hole / e Å -3 0.20/-0.21 S10

Table S9. Fractional Atomic Coordinates ( 10 4 ) and Equivalent Isotropic Displacement Parameters (Å 2 10 3 ) for 1ea. U eq is defined as 1/3 of of the trace of the orthogonalised U IJ tensor. Atom x y z U(eq) C1-240(3) 7172.3(8) 1934.4(11) 39.0(3) C2 1670(3) 7730.2(8) 1866.8(10) 38.8(3) N3 1212(3) 7039.0(9) 3795.7(10) 49.1(3) O4-5219(3) 6172.3(8) 379.5(10) 63.1(4) N5 2267(3) 8156.7(8) 1037.5(9) 42.1(3) C6-1941(3) 6935.6(9) 1104.9(11) 42.4(3) C7-3696(3) 6376.5(10) 1238.7(12) 45.4(4) C8 5029(3) 8490.1(9) 2409.8(11) 42.4(3) C9-357(3) 6832.1(9) 2934.2(11) 43.3(4) C10 3310(3) 7921.8(9) 2734.8(11) 42.3(3) C11 2968(3) 7553.9(10) 3681.1(11) 48.2(4) C12 4298(3) 8624.9(9) 1348.8(11) 42.4(3) C13-3810(3) 6031.1(10) 2219.5(13) 50.4(4) C14-2176(3) 6261.9(11) 3036.5(12) 50.5(4) C15 5548(3) 9153(1) 772.7(13) 52.1(4) C16 7123(3) 8887.9(10) 2884.2(13) 49.1(4) C17 8390(3) 9402.3(11) 2304.5(15) 56.5(5) C18-7213(4) 5641.8(11) 484.8(18) 63.0(5) C19 7592(4) 9533.8(11) 1266.0(15) 56.8(4) S11

Table S10. Anisotropic Displacement Parameters (Å 2 10 3 ) for 1ea. The Anisotropic displacement factor exponent takes the form: -2π 2 [h 2 a* 2 U 11 +2hka*b*U 12 + ]. Atom U 11 U 22 U 33 U 23 U 13 U 12 C1 42.0(7) 45.7(8) 28.9(6) 0.2(5) -0.7(5) 6.5(6) C2 43.3(7) 45.0(8) 27.7(6) -0.7(5) 0.2(5) 6.8(6) N3 56.8(8) 62.2(9) 27.5(6) 4.7(5) -2.6(5) 0.0(6) O4 68.3(8) 68.6(9) 49.9(7) 6.7(6) -16.8(6) -19.6(6) N5 49.0(7) 50.2(7) 26.5(6) 0.4(5) -2.0(5) 0.0(5) C6 46.6(7) 48.8(9) 31.3(7) 2.6(6) -2.5(6) 4.4(6) C7 44.5(8) 50.9(9) 40.1(7) -0.4(6) -4.4(6) 3.4(6) C8 43.4(7) 48.1(8) 35.2(7) -4.1(6) -1.3(6) 6.0(6) C9 48.0(8) 52.1(9) 29.6(7) 2.6(6) 1.2(6) 5.4(6) C10 46.0(7) 50.8(9) 29.7(7) -3.5(6) -2.2(5) 5.1(6) C11 53.5(8) 60.9(10) 28.9(7) -0.9(6) -7.3(6) 1.6(7) C12 44.7(7) 47.8(9) 34.5(7) -2.6(6) 1.7(6) 4.6(6) C13 50.0(8) 52.7(10) 48.6(9) 6.0(7) 2.7(7) -3.2(7) C14 54.4(9) 60.4(11) 36.7(7) 10.2(7) 3.7(6) -0.6(7) C15 57.2(9) 57.2(10) 42.2(8) 2.6(7) 6.7(7) 1.4(8) C16 49.9(8) 53.1(10) 43.6(8) -7.0(6) -4.1(6) 0.8(7) C17 48.3(9) 60.6(11) 60.1(10) -11.4(8) 0.4(8) -6.4(7) C18 52.2(10) 62.0(12) 73.4(12) -6.4(9) -7.4(9) -6.4(8) C19 55.0(9) 55.5(10) 60.9(10) 1.9(8) 11.1(8) -5.2(7) Table S11. Bond Lengths for 1ea Atom Atom Length/Å Atom Atom Length/Å C1 C2 1.411(2) C7 C13 1.412(2) C1 C6 1.402(2) C8 C10 1.431(2) C1 C9 1.430(2) C8 C12 1.414(2) C2 N5 1.3656(19) C8 C16 1.399(2) C2 C10 1.399(2) C9 C14 1.401(2) N3 C9 1.380(2) C10 C11 1.407(2) N3 C11 1.308(2) C12 C15 1.388(2) O4 C7 1.364(2) C13 C14 1.368(3) O4 C18 1.412(2) C15 C19 1.374(3) N5 C12 1.381(2) C16 C17 1.378(3) C6 C7 1.370(2) C17 C19 1.393(3) S12

Table S12. Bond Angles for 1ea Atom Atom Atom Angle/ Atom Atom Atom Angle/ C2 C1 C9 115.46(14) N3 C9 C1 123.45(15) C6 C1 C2 124.87(13) N3 C9 C14 118.81(14) C6 C1 C9 119.66(15) C14 C9 C1 117.74(14) N5 C2 C1 129.83(13) C2 C10 C8 107.12(13) N5 C2 C10 109.37(14) C2 C10 C11 118.23(15) C10 C2 C1 120.81(13) C11 C10 C8 134.65(15) C11 N3 C9 118.21(13) N3 C11 C10 123.78(15) C7 O4 C18 119.13(15) N5 C12 C8 108.93(14) C2 N5 C12 108.66(12) N5 C12 C15 129.06(14) C7 C6 C1 120.74(14) C15 C12 C8 122.01(15) O4 C7 C6 116.42(14) C14 C13 C7 119.65(17) O4 C7 C13 123.45(16) C13 C14 C9 122.09(15) C6 C7 C13 120.11(15) C19 C15 C12 117.42(16) C12 C8 C10 105.92(13) C17 C16 C8 118.94(16) C16 C8 C10 135.19(15) C16 C17 C19 120.91(17) C16 C8 C12 118.87(15) C15 C19 C17 121.82(17) S13

Table S13. Torsion Angles for 1ea A B C D Angle/ A B C D Angle/ C1 C2 N5 C12-179.71(14) C8 C12 C15 C19 1.6(2) C1 C2 C10 C8 179.18(13) C8 C16 C17 C19 0.8(3) C1 C2 C10 C11-1.2(2) C9 C1 C2 N5-179.74(14) C1 C6 C7 O4-178.34(14) C9 C1 C2 C10 0.2(2) C1 C6 C7 C13 0.0(2) C9 C1 C6 C7-0.7(2) C1 C9 C14 C13-0.2(2) C9 N3 C11 C10 1.5(3) C2 C1 C6 C7 178.46(14) C10 C2 N5 C12 0.39(17) C2 C1 C9 N3 1.9(2) C10 C8 C12 N5-0.83(16) C2 C1 C9 C14-178.43(14) C10 C8 C12 C15 179.50(15) C2 N5 C12 C8 0.29(17) C10 C8 C16 C17 178.83(17) C2 N5 C12 C15 179.93(16) C11 N3 C9 C1-2.8(2) C2 C10 C11 N3 0.4(3) C11 N3 C9 C14 177.57(16) N3 C9 C14 C13 179.47(16) C12 C8 C10 C2 1.05(16) O4 C7 C13 C14 178.78(16) C12 C8 C10 C11-178.42(18) N5 C2 C10 C8-0.91(17) C12 C8 C16 C17 0.5(2) N5 C2 C10 C11 178.67(14) C12 C15 C19 C17-0.3(3) N5 C12 C15 C19-178.01(16) C16 C8 C10 C2-177.43(17) C6 C1 C2 N5 1.1(3) C16 C8 C10 C11 3.1(3) C6 C1 C2 C10-179.02(14) C16 C8 C12 N5 177.94(13) C6 C1 C9 N3-178.90(14) C16 C8 C12 C15-1.7(2) C6 C1 C9 C14 0.8(2) C16 C17 C19 C15-0.9(3) C6 C7 C13 C14 0.6(3) C18 O4 C7 C6-174.87(16) C7 C13 C14 C9-0.4(3) C18 O4 C7 C13 6.9(3) C8 C10 C11 N3 179.82(16) S14

Table S14. Hydrogen Atom Coordinates (Å 10 4 ) and Isotropic Displacement Parameters (Å 2 10 3 ) for 1ea. Atom x y z U(eq) H6-1877 7161 457 51 H11 4053 7684 4259 58 H13-4990 5649 2310 61 H14-2275 6033 3681 61 H15 5023 9245 80 62 H16 7650 8807 3580 59 H17 9797 9665 2611 68 H18A -8165 5574-175 94 H18B -8391 5809 990 94 H18C -6437 5182 711 94 H19 8467 9889 896 68 H5 1580(40) 8140(12) 403(17) 55(5) S15

Experimental Single crystals of C16H12N2O (1ea) were recrystallized from EtOH. A suitable crystal was selected and glued with acrylic glue to the glass stick on a SuperNova, Dual, AtlasS2 diffractometer. The crystal was kept at 100.00(10) K during data collection. The structure was solved with the ShelXD structure solution program 1 using Olex2 interface 2 and refined with the ShelXL refinement package 3 using Least Squares minimization algorithm. Crystal structure determination of 1ea Crystal Data for C16H12N2O (M =248.28 g/mol): monoclinic, space group P21/c (no. 14), a = 5.1053(3) Å, b = 18.1238(12) Å, c = 12.8535(7) Å, β = 93.383(6), V = 1187.22(13) Å 3, Z = 4, T = 292.96(15) K, μ(cukα) = 0.706 mm -1, Dcalc = 1.389 g/cm 3, 7012 reflections measured (8.444 2Θ 147.664 ), 2319 unique (Rint = 0.0304, Rsigma = 0.0305) which were used in all calculations. The final R1 was 0.0460 (I > 2σ(I)) and wr2 was 0.1333 (all data). Refinement model description Number of restraints - 0, number of constraints - unknown. Details: 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Aromatic/amide H refined with riding coordinates: C6(H6), C11(H11), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C19(H19) 2.b Idealised Me refined as rotating group: C18(H18a,H18b,H18c) S16

Figure S3. ORTEP drawing of compound 1ea: showing 50% probability amplitude displacement ellipsoids. Figure S4. Packing of molecules of compound 1ea in the crystalline lattice S17

Spectral Charts

S19

Chemical Formula: C 16 H 13 N 2 + (M+H) + Exact Mass: 233.1073 S20

S21

S22

Chemical Formula: C 17 H 15 N 2 + (M+H) + Exact Mass: 247.1230 S23

S24

S25

Chemical Formula: C 22 H 17 N 2 + (M+H) + Exact Mass: 309.1386 S26

Me N N 1ad S27

Me N N 1ad S28

Me NH N 1ad Chemical Formula: C 21 H 23 N 2 + (M+H) + Exact Mass: 303.1856 S29

S30

S31

Chemical Formula: C 15 H 11 N 2 + (M+H) + Exact Mass: 219.0917 S32

S33

S34

Chemical Formula: C 16 H 13 N 2 + (M+H) + Exact Mass: 233.1073 S35

S36

S37

Chemical Formula: C 21 H 15 N 2 + (M+H) + Exact Mass: 295.1230 S38

S39

S40

Chemical Formula: C 20 H 21 N 2 + (M+H) + Exact Mass: 289.1699 S41

S42

S43

Chemical Formula: C 20 H 14 N 3 + (M+H) + Exact Mass: 296.1182 S44

S45

S46

Chemical Formula: C 16 H 13 N 2 + (M+H) + Exact Mass: 233.1073 S47

S48

S49

Chemical Formula: C 17 H 15 N 2 + (M+H) + Exact Mass: 247.1230 S50

S51

S52

Chemical Formula: C 22 H 17 N 2 + (M+H) + Exact Mass: 309.1386 S53

S54

S55

Chemical Formula: C 17 H 15 N 2 + (M+H) + Exact Mass: 247.1230 S56

S57

S58

Chemical Formula: C 18 H 17 N 2 + (M+H) + Exact Mass: 261.1386 S59

S60

S61

Chemical Formula: C 23 H 19 N 2 + (M+H) + Exact Mass: 323.1543 S62

S63

S64

Chemical Formula: C 16 H 13 N 2 O + (M+H) + Exact Mass: 249.1022 S65

S66

S67

Chemical Formula: C 17 H 15 N 2 O 2 + (M+H) + Exact Mass: 279.1128 S68

S69

S70

Chemical Formula: C 18 H 17 N 2 O 2 + (M+H) + Exact Mass: 293.1285 S71