Supporting Information
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- Τελαμών Λέανδρος Αλαφούζος
- 5 χρόνια πριν
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1 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
2 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 Temperature/K (10) Crystal system tetragonal Space group I4 1 cd a/å (15) b/å (15) c/å (18) α/ 90 β/ 90 γ/ 90 Volume/Å (11) Z 16 ρ calc g/cm µ/mm F(000) Crystal size/mm Radiation CuKα (λ = ) 2Θ range for data collection/ 8.84 to Index ranges -23 h 24, -22 k 22, -15 l 14 Reflections collected Independent reflections 2526 [R int = , R sigma = ] Data/restraints/parameters 2526/1/187 Goodness-of-fit on F Final R indexes [I>=2σ (I)] R 1 = , wr 2 = Final R indexes [all data] R 1 = , wr 2 = Largest diff. peak/hole / e Å /-0.32 Flack parameter 0.02(9) S2
3 Table S2. Fractional Atomic Coordinates ( 10 4 ) and Equivalent Isotropic Displacement Parameters (Å ) 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) C (12) (12) (19) 12.9(5) C (9) (8) (9) 13.4(5) C (9) (7) (11) 13.9(5) C (9) (7) (11) 14.2(5) N (9) (7) (9) 14.3(4) C (9) (6) (12) 13.5(5) C (12) (12) (18) 14.5(5) N (10) (10) (15) 14.7(4) C (12) (12) 6040(2) 15.1(5) C (12) (12) (19) 14.4(5) C (14) (13) 6755(2) 19.8(5) C (13) (13) 7140(2) 17.1(5) C (11) (12) (19) 13.3(5) C (12) (12) 5004(2) 15.1(5) C (12) (12) 5024(2) 17.0(5) C (12) (13) 4258(2) 14.9(5) C (13) (12) 5707(2) 19.6(5) O (9) (9) (14) 18.9(4) O (9) (9) (14) 18.3(4) C (14) (13) 3848(2) 22.3(6) C (15) (13) 7749(2) 21.3(6) S3
4 Table S3. Anisotropic Displacement Parameters (Å ) 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 C (11) 13.1(11) 14.3(13) -0.6(9) -1.2(9) 1.2(8) C (11) 13.4(11) 13.5(12) 0.6(9) -0.4(9) 1.1(8) C (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) C (11) 14.2(11) 11.6(12) 1.9(9) 0.2(9) 0.1(8) C (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) C (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) C (13) 15.8(12) 23.8(15) -4.4(10) -2.3(11) -0.6(10) C (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 C (3) C7 C (3) C12 N (3) N2 C (3) C12 C (3) C9 C (3) C14 C C9 C (4) C14 C C9 O (3) C14 C (3) C3 C (4) C15 C C3 C (4) C15 C (3) C10 C (4) C5 N C10 O (3) C5 C (3) C1 C (4) N1 C O1 C (3) C6 C (3) O2 C (3) S4
5 Table S5. Bond Angles for 1fa. Atom Atom Atom Angle/ Atom Atom Atom Angle/ N2 C12 C (2) C8 C7 C (2) N2 C12 C (2) C13 N2 C (2) C11 C12 C (2) C8 C9 C (2) C6 C14 C O1 C9 C (2) C13 C14 C (14) O1 C9 C (2) C13 C14 C (14) C9 C8 C (2) C14 C15 C C4 C3 C (2) C1 C15 C (15) C5 C4 C (2) C1 C15 C (15) N2 C13 C (2) N1 C5 C C11 C10 C (2) C4 C5 C (15) O2 C10 C (2) C4 C5 N (15) O2 C10 C (2) C6 N1 C C2 C1 C (2) N1 C6 C C10 C11 C (2) C7 C6 C (15) C1 C2 C (2) C7 C6 N (15) C9 O1 C (2) C6 C7 C (2) C10 O2 C (2) C6 C7 C (2) S5
6 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 C (2) C12 N2 C13 C14-0.3(3) N2 C12 C11 C (2) C14 C15 C5 N1 0.0 C9 C10 C11 C12 4.4(4) C14 C15 C5 C (2) C9 C10 O2 C (2) C14 C15 C1 C (18) C8 C9 C10 C11-3.8(4) C14 C6 C7 C12 2.2(3) C8 C9 C10 O (2) C14 C6 C7 C (18) C8 C9 O1 C17-1.7(4) C15 C14 C6 N1 0.0 C4 C5 N1 C (2) C15 C14 C6 C (2) C4 C3 C2 C1-1.2(4) C15 C14 C13 N (17) C13 C14 C15 C (2) C15 C5 N1 C6 0.0 C13 C14 C15 C1 6.2(3) C15 C5 C4 C3 2.1(3) C13 C14 C6 N (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 C C10 C9 O1 C (2) C5 N1 C6 C (2) C1 C15 C5 N (19) N1 C5 C4 C (18) C1 C15 C5 C4-3.9(2) N1 C6 C7 C (16) C11 C12 C7 C (2) N1 C6 C7 C8 3.5(3) C11 C12 C7 C8-1.6(3) C6 C14 C15 C5 0.0 C11 C12 N2 C (2) C6 C14 C15 C (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 C (2) O1 C9 C8 C (2) C7 C12 N2 C13-0.5(3) O1 C9 C10 C (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 C (2) S6
7 Table S7. Hydrogen Atom Coordinates (Å 10 4 ) and Isotropic Displacement Parameters (Å ) for 1fa Atom x y z U(eq) H H H H H1A H H H16A H16B H16C H17A H17B H17C 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 (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 = g/mol): tetragonal, space group I41cd (no. 110), a = (15) Å, c = (18) Å, V = (11) Å 3, Z = 16, T = (10) K, μ(cukα) = mm -1, Dcalc = g/cm 3, reflections measured (8.84 2Θ ), 2526 unique (Rint = , Rsigma = ) which were used in all calculations. The final R1 was (I > 2σ(I)) and wr2 was (all data). (1) Sheldrick, G.M. Acta Cryst. 2008, A64, (2) Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. J. Appl. Cryst. 2009, 42, (3) Sheldrick, G.M. Acta Cryst. 2015, C71, 3-8. S7
8 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
9 Figure S2. Packing of molecules (16 units) of compound 1fa in the crystalline lattice view along axis c. S9
10 Table S8. Crystal data and structure refinement for compound 1ea Identification code 1ea Empirical formula C 16 H 12 N 2 O Formula weight Temperature/K (15) Crystal system monoclinic Space group P2 1 /c a/å (3) b/å (12) c/å (7) α/ 90 β/ (6) γ/ 90 Volume/Å (13) Z 4 ρ calc g/cm µ/mm F(000) Crystal size/mm Radiation CuKα (λ = ) 2Θ range for data collection/ to Index ranges -5 h 6, -22 k 15, -15 l 15 Reflections collected 7012 Independent reflections 2319 [R int = , R sigma = ] Data/restraints/parameters 2319/0/177 Goodness-of-fit on F Final R indexes [I>=2σ (I)] R 1 = , wr 2 = Final R indexes [all data] R 1 = , wr 2 = Largest diff. peak/hole / e Å /-0.21 S10
11 Table S9. Fractional Atomic Coordinates ( 10 4 ) and Equivalent Isotropic Displacement Parameters (Å ) 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) (8) (11) 39.0(3) C2 1670(3) (8) (10) 38.8(3) N3 1212(3) (9) (10) 49.1(3) O4-5219(3) (8) 379.5(10) 63.1(4) N5 2267(3) (8) (9) 42.1(3) C6-1941(3) (9) (11) 42.4(3) C7-3696(3) (10) (12) 45.4(4) C8 5029(3) (9) (11) 42.4(3) C9-357(3) (9) (11) 43.3(4) C (3) (9) (11) 42.3(3) C (3) (10) (11) 48.2(4) C (3) (9) (11) 42.4(3) C (3) (10) (13) 50.4(4) C (3) (11) (12) 50.5(4) C (3) 9153(1) 772.7(13) 52.1(4) C (3) (10) (13) 49.1(4) C (3) (11) (15) 56.5(5) C (4) (11) 484.8(18) 63.0(5) C (4) (11) (15) 56.8(4) S11
12 Table S10. Anisotropic Displacement Parameters (Å ) 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) C (7) 50.8(9) 29.7(7) -3.5(6) -2.2(5) 5.1(6) C (8) 60.9(10) 28.9(7) -0.9(6) -7.3(6) 1.6(7) C (7) 47.8(9) 34.5(7) -2.6(6) 1.7(6) 4.6(6) C (8) 52.7(10) 48.6(9) 6.0(7) 2.7(7) -3.2(7) C (9) 60.4(11) 36.7(7) 10.2(7) 3.7(6) -0.6(7) C (9) 57.2(10) 42.2(8) 2.6(7) 6.7(7) 1.4(8) C (8) 53.1(10) 43.6(8) -7.0(6) -4.1(6) 0.8(7) C (9) 60.6(11) 60.1(10) -11.4(8) 0.4(8) -6.4(7) C (10) 62.0(12) 73.4(12) -6.4(9) -7.4(9) -6.4(8) C (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 C (2) C7 C (2) C1 C (2) C8 C (2) C1 C (2) C8 C (2) C2 N (19) C8 C (2) C2 C (2) C9 C (2) N3 C (2) C10 C (2) N3 C (2) C12 C (2) O4 C (2) C13 C (3) O4 C (2) C15 C (3) N5 C (2) C16 C (3) C6 C (2) C17 C (3) S12
13 Table S12. Bond Angles for 1ea Atom Atom Atom Angle/ Atom Atom Atom Angle/ C2 C1 C (14) N3 C9 C (15) C6 C1 C (13) N3 C9 C (14) C6 C1 C (15) C14 C9 C (14) N5 C2 C (13) C2 C10 C (13) N5 C2 C (14) C2 C10 C (15) C10 C2 C (13) C11 C10 C (15) C11 N3 C (13) N3 C11 C (15) C7 O4 C (15) N5 C12 C (14) C2 N5 C (12) N5 C12 C (14) C7 C6 C (14) C15 C12 C (15) O4 C7 C (14) C14 C13 C (17) O4 C7 C (16) C13 C14 C (15) C6 C7 C (15) C19 C15 C (16) C12 C8 C (13) C17 C16 C (16) C16 C8 C (15) C16 C17 C (17) C16 C8 C (15) C15 C19 C (17) S13
14 Table S13. Torsion Angles for 1ea A B C D Angle/ A B C D Angle/ C1 C2 N5 C (14) C8 C12 C15 C19 1.6(2) C1 C2 C10 C (13) C8 C16 C17 C19 0.8(3) C1 C2 C10 C11-1.2(2) C9 C1 C2 N (14) C1 C6 C7 O (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 C (14) C10 C2 N5 C (17) C2 C1 C9 N3 1.9(2) C10 C8 C12 N5-0.83(16) C2 C1 C9 C (14) C10 C8 C12 C (15) C2 N5 C12 C8 0.29(17) C10 C8 C16 C (17) C2 N5 C12 C (16) C11 N3 C9 C1-2.8(2) C2 C10 C11 N3 0.4(3) C11 N3 C9 C (16) N3 C9 C14 C (16) C12 C8 C10 C2 1.05(16) O4 C7 C13 C (16) C12 C8 C10 C (18) N5 C2 C10 C8-0.91(17) C12 C8 C16 C17 0.5(2) N5 C2 C10 C (14) C12 C15 C19 C17-0.3(3) N5 C12 C15 C (16) C16 C8 C10 C (17) C6 C1 C2 N5 1.1(3) C16 C8 C10 C11 3.1(3) C6 C1 C2 C (14) C16 C8 C12 N (13) C6 C1 C9 N (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 C (16) C7 C13 C14 C9-0.4(3) C18 O4 C7 C13 6.9(3) C8 C10 C11 N (16) S14
15 Table S14. Hydrogen Atom Coordinates (Å 10 4 ) and Isotropic Displacement Parameters (Å ) for 1ea. Atom x y z U(eq) H H H H H H H H18A H18B H18C H H5 1580(40) 8140(12) 403(17) 55(5) S15
16 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 (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 = g/mol): monoclinic, space group P21/c (no. 14), a = (3) Å, b = (12) Å, c = (7) Å, β = (6), V = (13) Å 3, Z = 4, T = (15) K, μ(cukα) = mm -1, Dcalc = g/cm 3, 7012 reflections measured ( Θ ), 2319 unique (Rint = , Rsigma = ) which were used in all calculations. The final R1 was (I > 2σ(I)) and wr2 was (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
17 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
18 Spectral Charts
19 S19
20 Chemical Formula: C 16 H 13 N 2 + (M+H) + Exact Mass: S20
21 S21
22 S22
23 Chemical Formula: C 17 H 15 N 2 + (M+H) + Exact Mass: S23
24 S24
25 S25
26 Chemical Formula: C 22 H 17 N 2 + (M+H) + Exact Mass: S26
27 Me N N 1ad S27
28 Me N N 1ad S28
29 Me NH N 1ad Chemical Formula: C 21 H 23 N 2 + (M+H) + Exact Mass: S29
30 S30
31 S31
32 Chemical Formula: C 15 H 11 N 2 + (M+H) + Exact Mass: S32
33 S33
34 S34
35 Chemical Formula: C 16 H 13 N 2 + (M+H) + Exact Mass: S35
36 S36
37 S37
38 Chemical Formula: C 21 H 15 N 2 + (M+H) + Exact Mass: S38
39 S39
40 S40
41 Chemical Formula: C 20 H 21 N 2 + (M+H) + Exact Mass: S41
42 S42
43 S43
44 Chemical Formula: C 20 H 14 N 3 + (M+H) + Exact Mass: S44
45 S45
46 S46
47 Chemical Formula: C 16 H 13 N 2 + (M+H) + Exact Mass: S47
48 S48
49 S49
50 Chemical Formula: C 17 H 15 N 2 + (M+H) + Exact Mass: S50
51 S51
52 S52
53 Chemical Formula: C 22 H 17 N 2 + (M+H) + Exact Mass: S53
54 S54
55 S55
56 Chemical Formula: C 17 H 15 N 2 + (M+H) + Exact Mass: S56
57 S57
58 S58
59 Chemical Formula: C 18 H 17 N 2 + (M+H) + Exact Mass: S59
60 S60
61 S61
62 Chemical Formula: C 23 H 19 N 2 + (M+H) + Exact Mass: S62
63 S63
64 S64
65 Chemical Formula: C 16 H 13 N 2 O + (M+H) + Exact Mass: S65
66 S66
67 S67
68 Chemical Formula: C 17 H 15 N 2 O 2 + (M+H) + Exact Mass: S68
69 S69
70 S70
71 Chemical Formula: C 18 H 17 N 2 O 2 + (M+H) + Exact Mass: S71
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Supporting Information Multifunctinality and Crystal Dynamics of Highly Stable Porous Metal-Organic Framework [Zn 4 O(NTB) 2 ] Eun Young Lee, Seung Yeon Jang, and Myunghyun Paik Suh* School of Chemistry,
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chlorostibine Iou-Sheng Ke and François P. Gabbai Department of Chemistry, Texas A&M University, College Station, TX
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Supporting Information. Palladium Complexes with Bulky Diphosphine. Synthesis of (Bio-) Adipic Acid from Pentenoic. Acid Mixtures.
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data reports 2-(4-Methylphenyl)-2-oxoethyl 3,4-dimethoxybenzoate Structure description Synthesis and crystallization Refinement
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metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 [1,2-Bis(1H-benzimidazol-2-yl-jN 3 )- ethane]dichloridozinc(ii) Yan-Ling Zhou, a Ming-Hua Zeng a and Seik
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SUPPORTING INFORMATION Pyrrolo[2,3-d:5,4-d']bisthiazoles: Alternate Synthetic Routes and a Comparative Study to Analogous Fused-ring Bithiophenes Eric J. Uzelac, Casey B. McCausland, and Seth C. Rasmussen*
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SUPPLEMENTARY MATERIAL. A Facile and Convenient Approach for the Synthesis of Novel Sesamol-Oxazine and Quinoline- Oxazine Hybrids
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Table S1 Selected bond lengths [Å] and angles [ ] for complexes 1 8. Complex 1 Zn(1) O(1) 1.969(2) Zn(1) O(5) 1.989(3) Zn(1) O(6) 1.930(3) Zn(1) O(4) a 1.954(4) Zn(1) O(3) a 2.519(25) O(6) Zn(1) O(4) a
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Supporting Information. Generation Response. Physics & Chemistry of CAS, 40-1 South Beijing Road, Urumqi , China. China , USA
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data reports ISSN 2056-9890 Crystal structure of 3b-acetoxyandrosta- 5,16-dien-17-yl trifluoromethanesulfonate Shengjun Zhou, a Huaqi Huang, b Ting Zhang, b Dangfeng Wang b and Rongbin Huang b * a Hangzhou
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ISSN 2414-3146 N,N,N-Triethylethanaminium 5,11,17,23-tetra-tertbutyl-25-[(ethoxycarbonyl)methoxy]-26,28-dihydroxy-27-oxido-2,8,14,20-tetrathiacalix[4]arene: a molecular salt Received 14 September 2016
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