Supplementary File. Modification of Boc-protected CAN508 via acylation and Suzuki-Miyaura Coupling
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1 Supplementary File Modification of Boc-protected CA508 via acylation and Suzuki-Miyaura Coupling Martin Pisár, Eva Schütznerová 2, Filip Hančík, Igor Popa 3, Zdeněk Trávníček 3 and Petr Cankař, * Department of rganic Chemistry, Faculty of Science, Palacký University, 7. listopadu 92/2, lomouc, Czech Republic; martin.pisar0@upol.cz (M.P.); Filda.Hancik@seznam.cz (F.H.) 2 Institute of Molecular and Translation Medicine, Faculty of Medicine, Palacký University, Hněvotínská 5, lomouc, Czech Republic; eva.schutznerova@upol.cz 3 Department of Inorganic Chemistry, Faculty of Science, Palacký University, 7. listopadu 92/2, lomouc, Czech Republic; igor.popa@upol.cz (I.P.); zdenek.travnicek@upol.cz (Z.T.) * Correspondence: petr.cankar@upol.cz; Tel.: Table of Contents. H and 3 C MR spectra... S2 2. Crystallographic data for structures 5 and 3... S23 S
2 H and 3 C MR spectra of 3 H 2 H 2 H 2 H 2 S2
3 H and 3 C MR spectra of 5 H 2 H 2 H H 2 H 2 H S3
4 H and 3 C MR spectra of 6 C C H Si impurity C C H Si S4
5 H and 3 C MR spectra of 7 H H 2 H 2 Si H H 2 H 2 Si S5
6 H and 3 C MR spectra of 8 H 2 H 2 Si H 2 H 2 Si S6
7 H and 3 C MR spectra of 9 S7
8 H and 3 C MR spectra of 0 H H 2 H 2 H H 2 H 2 S8
9 H and 3 C MR spectra of c H 2 H Br H 2 H Br S9
10 H and 3 C MR spectra of 2b S0
11 H and 3 C MR spectra of 2c S
12 H and 3 C MR spectra of 2d S2
13 H and 3 C MR spectra of 2e S3
14 H and 3 C MR spectra of 2f S4
15 H and 3 C MR spectra of 2g S5
16 H and 3 C MR spectra of 2h S6
17 H and 3 C MR spectra of 2i S7
18 H and 3 C MR spectra of 2j S8
19 H and 3 C MR spectra of 2k S9
20 H and 3 C MR spectra of 2l S20
21 H and 3 C MR spectra of 2m S2
22 H and 3 C MR spectra of 2n S22
23 Single crystal X-ray analysis The single crystal X-ray data of 3 (CCDC 45332) and 5 (CCDC ) were obtained using an Xcalibur2 diffractometer (xford Diffraction Ltd., UK) equipped with a Sapphire2 CCD detector, and with MoKα radiation (monochromator Enhance, xford Diffraction Ltd.) and ω- scan technique at 20 K. Additional details regarding structure determinations, such as crystal data and structure refinements, selected bond lengths and angles of covalent as well as noncovalent contacts are summarized below. Data collection and reduction were performed by the CrysAlis software package. The structure was solved by direct methods using SHELX 2 and refined on F 2 using a full-matrix least-squares procedure. All H-atoms were located from difference Fourier maps and refined using a riding model, with C H = 0.95 Å (CH) aromatic, 0.98 Å (CH 3 ), H = 0.84 Å and H = 0.88 Å (H) aromatic, and with U iso (H) =.2U eq (CH, H, H) and.5u eq (CH 3 ). The H-atoms of the H 2 groups were refined freely. Molecular graphics were drawn using DIAMD. 3 Crystal data and structure refinements for 3 and 5 are given in Tables S and S2, sets of covalent and non-covalent bonding in Tables S3 S6, and parts of crystal structures are depicted in Figures S S4 (see below). xford Diffraction, CrysAlis RED and CrysAlis CCD Software (Version ), xford Diffraction Ltd., Abingdon, xfordshire, UK. 2 G.M. Sheldrick, A short history of SHELX, Acta Crystallogr., Sect. A 64 (2008) K. Brandenburg DIAMD, Release 4.., Crystal Impact GbR, Bonn, Germany, 205. S23
24 Table S. Crystal data and structure refinement for 5. Empirical formula C 4 H Formula weight Temperature 30(2) K Wavelength Å Crystal system Monoclinic Space group P2/c Unit cell dimensions a = (2) Å α= 90. b = 9.759(4) Å β= (3). c = (9) Å γ = 90. Volume (0) Å 3 Z 4 Density (calculated).427 Mg/m 3 Absorption coefficient 0.05 mm - F(000) 672 Crystal size x x 0.50 mm 3 Theta range for data collection to Index ranges -7 h 7, -9 k, -28 l 28 Reflections collected 204 Independent reflections 260 [R(int) = ] Completeness to theta = % Absorption correction Semi-empirical from equivalents Max. and min. transmission.000 and Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 260 / 0 / 227 Goodness-of-fit on F Final R indices [I>2sigma(I)] R = 0.032, wr2 = R indices (all data) R = , wr2 = Largest diff. peak and hole 0.20 and e. Å -3 S24
25 Table S2. Crystal data and structure refinement for 3. Empirical formula C 9 H Formula weight Temperature 20(2) K Wavelength Å Crystal system Triclinic Space group P- Unit cell dimensions a = 6.060(2) Å α= (4). b =.9685(5) Å β= (4). c = (7) Å γ = 97.02(3). Volume (8) Å 3 Z 2 Density (calculated).335 Mg/m 3 Absorption coefficient mm - F(000) 444 Crystal size x x mm 3 Theta range for data collection 3.06 to Index ranges -7 h 7, -2 k 4, -7 l 7 Reflections collected 9776 Independent reflections 3667 [R(int) = ] Completeness to theta = % Absorption correction Semi-empirical from equivalents Max. and min. transmission.000 and Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 3667 / 0 / 293 Goodness-of-fit on F 2.06 Final R indices [I>2sigma(I)] R = , wr2 = R indices (all data) R = , wr2 = 0.02 Largest diff. peak and hole 0.87 and e. Å -3 Table S3. Bond lengths [Å ] and angles [ ] for 5. ()-C(7).3663(5) ()-H(A) ()-C().3744(6) ()-C(0).3933(6) ()-(2).4096(5) C()-(6).373(7) C()-C(2).3752(8) (2)-C(3).326(6) (2)-C(0).2097(6) C(2)-(3).3805(6) C(2)-C(3).4322(8) (3)-C(0).3226(6) (3)-C().5033(5) (3)-(4).278(5) C(3)-(5).3446(7) (4)-C(4).490(7) C(4)-C(9).3896(9) C(4)-C(5).392(9) (5)-H(5D) 0.857(7) S25
26 (5)-H(5C) 0.908(8) C(5)-C(6).3836(8) C(5)-H(5A) (6)-H(6D) 0.898(8) (6)-H(6C) 0.88(7) C(6)-C(7).383(2) C(6)-H(6A) C(7)-C(8).3856(9) C(8)-C(9).3793(8) C(8)-H(8A) C(9)-H(9A) C()-C(4).539(9) C()-C(3).544(9) C()-C(2).536(9) C(2)-H(2A) C(2)-H(2B) C(2)-H(2C) C(3)-H(3A) C(3)-H(3B) C(3)-H(3C) C(4)-H(4A) C(4)-H(4B) C(4)-H(4C) C(7)-()-H(A) 09.5 C()-()-C(0) 25.79() C()-()-(2).54(0) C(0)-()-(2) 22.09(0) (6)-C()-() 23.48(2) (6)-C()-C(2) 29.73(2) ()-C()-C(2) 06.78() C(3)-(2)-() 03.99(0) C()-C(2)-(3) 22.7(2) C()-C(2)-C(3) 05.50() (3)-C(2)-C(3) 3.69(2) C(0)-(3)-C() 9.47(0) (4)-(3)-C(2) 4.8() (2)-C(3)-(5) 22.6(2) (2)-C(3)-C(2) 2.4() (5)-C(3)-C(2) 25.70(2) (3)-(4)-C(4) 3.80() C(9)-C(4)-C(5) 9.3(2) C(9)-C(4)-(4) 24.42(2) C(5)-C(4)-(4) 6.44(2) C(3)-(5)-H(5D) 7.6() C(3)-(5)-H(5C) 20.4(0) H(5D)-(5)-H(5C) 20.(5) C(6)-C(5)-C(4) 20.52(3) C(6)-C(5)-H(5A) 9.7 C(4)-C(5)-H(5A) 9.7 C()-(6)-H(6D) 3.() C()-(6)-H(6C).4() H(6D)-(6)-H(6C) 4.6(5) C(7)-C(6)-C(5) 9.80(3) C(7)-C(6)-H(6A) 20. C(5)-C(6)-H(6A) 20. ()-C(7)-C(6) 7.73(2) S26
27 ()-C(7)-C(8) 22.26(3) C(6)-C(7)-C(8) 20.0(2) C(9)-C(8)-C(7) 20.2(3) C(9)-C(8)-H(8A) 9.9 C(7)-C(8)-H(8A) 9.9 C(8)-C(9)-C(4) 20.3(3) C(8)-C(9)-H(9A) 9.8 C(4)-C(9)-H(9A) 9.8 (2)-C(0)-(3) 27.6(2) (2)-C(0)-() 2.00(2) (3)-C(0)-().37() (3)-C()-C(4).2() (3)-C()-C(3) 0.98(0) C(4)-C()-C(3) 0.2(2) (3)-C()-C(2) 08.0(0) C(4)-C()-C(2) 3.04(2) C(3)-C()-C(2).75(2) C()-C(2)-H(2A) 09.5 C()-C(2)-H(2B) 09.5 H(2A)-C(2)-H(2B) 09.5 C()-C(2)-H(2C) 09.5 H(2A)-C(2)-H(2C) 09.5 H(2B)-C(2)-H(2C) 09.5 C()-C(3)-H(3A) 09.5 C()-C(3)-H(3B) 09.5 H(3A)-C(3)-H(3B) 09.5 C()-C(3)-H(3C) 09.5 H(3A)-C(3)-H(3C) 09.5 H(3B)-C(3)-H(3C) 09.5 C()-C(4)-H(4A) 09.5 C()-C(4)-H(4B) 09.5 H(4A)-C(4)-H(4B) 09.5 C()-C(4)-H(4C) 09.5 H(4A)-C(4)-H(4C) 09.5 H(4B)-C(4)-H(4C) 09.5 S27
28 Table S4. Bond lengths [Å] and angles [ ] for 3. ()-C(0).322(2) ()-C().482(9) (2)-C(0).207(2) (3)-C(5).358(2) (3)-C(7).405(9) (4)-C(5).950(9) (5)-C(5).323(2) (5)-C(6).4892(9) ()-C(3).374(2) ()-C(0).386(2) ()-(2).409(9) (2)-C().38(2) (3)-(4).2773(9) (3)-C(2).374(2) (4)-C(4).48(2) (5)-C().355(2) (5)-H(5B) 0.90(2) (5)-H(5A) 0.87(2) (6)-C(3).342(2) (6)-H(6B) 0.88(2) (6)-H(6A) 0.88(2) C()-C(2).437(2) C(2)-C(3).382(2) C(4)-C(9).387(2) C(4)-C(5).395(2) C(5)-C(6).377(2) C(5)-H(5C) C(6)-C(7).382(2) C(6)-H(6C) C(7)-C(8).375(2) C(8)-C(9).38(2) C(8)-H(8A) C(9)-H(9A) C()-C(2).505(3) C()-C(4).509(2) C()-C(3).56(2) C(2)-H(2A) C(2)-H(2B) C(2)-H(2C) C(3)-H(3A) C(3)-H(3B) C(3)-H(3C) C(4)-H(4A) C(4)-H(4B) C(4)-H(4C) C(6)-C(9).52(2) C(6)-C(7).509(3) C(6)-C(8).59(3) C(7)-H(7A) C(7)-H(7B) C(7)-H(7C) C(8)-H(8A) C(8)-H(8B) C(8)-H(8C) S28
29 C(9)-H(9A) C(9)-H(9B) C(9)-H(9C) C(0)-()-C() 9.67(2) C(5)-(3)-C(7) 5.27(2) C(5)-(5)-C(6) 9.3(2) C(3)-()-C(0) 26.6(4) C(3)-()-(2).78(2) C(0)-()-(2) 2.79(3) C()-(2)-() 04.20(2) (4)-(3)-C(2) 4.5(3) (3)-(4)-C(4) 4.32(3) C()-(5)-H(5B) 2.5(3) C()-(5)-H(5A) 6.7(2) H(5B)-(5)-H(5A) 4.8(8) C(3)-(6)-H(6B) 8.4(3) C(3)-(6)-H(6A) 3.6(3) H(6B)-(6)-H(6A) 7.0(9) (2)-C()-(5) 22.9(5) (2)-C()-C(2) 2.7(4) (5)-C()-C(2) 25.60(5) (3)-C(2)-C(3) 22.59(4) (3)-C(2)-C() 3.90(4) C(3)-C(2)-C() 05.48(4) (6)-C(3)-() 24.26(5) (6)-C(3)-C(2) 29.34(5) ()-C(3)-C(2) 06.37(4) C(9)-C(4)-C(5) 9.42(5) C(9)-C(4)-(4) 5.42(4) C(5)-C(4)-(4) 25.2(4) C(6)-C(5)-C(4) 9.85(5) C(6)-C(5)-H(5C) 20. C(4)-C(5)-H(5C) 20. C(5)-C(6)-C(7) 9.58(5) C(5)-C(6)-H(6C) 20.2 C(7)-C(6)-H(6C) 20.2 C(8)-C(7)-C(6) 2.45(5) C(8)-C(7)-(3) 7.53(4) C(6)-C(7)-(3) 20.98(4) C(7)-C(8)-C(9) 8.83(5) C(7)-C(8)-H(8A) 20.6 C(9)-C(8)-H(8A) 20.6 C(8)-C(9)-C(4) 20.8(5) C(8)-C(9)-H(9A) 9.6 C(4)-C(9)-H(9A) 9.6 (2)-C(0)-() 27.56(5) (2)-C(0)-() 2.9(5) ()-C(0)-() 0.53(4) ()-C()-C(2) 07.60(4) ()-C()-C(4).64(3) C(2)-C()-C(4) 3.0(6) ()-C()-C(3) 0.38(3) C(2)-C()-C(3).66(6) C(4)-C()-C(3) 0.92(5) C()-C(2)-H(2A) 09.5 S29
30 C()-C(2)-H(2B) 09.5 H(2A)-C(2)-H(2B) 09.5 C()-C(2)-H(2C) 09.5 H(2A)-C(2)-H(2C) 09.5 H(2B)-C(2)-H(2C) 09.5 C()-C(3)-H(3A) 09.5 C()-C(3)-H(3B) 09.5 H(3A)-C(3)-H(3B) 09.5 C()-C(3)-H(3C) 09.5 H(3A)-C(3)-H(3C) 09.5 H(3B)-C(3)-H(3C) 09.5 C()-C(4)-H(4A) 09.5 C()-C(4)-H(4B) 09.5 H(4A)-C(4)-H(4B) 09.5 C()-C(4)-H(4C) 09.5 H(4A)-C(4)-H(4C) 09.5 H(4B)-C(4)-H(4C) 09.5 (4)-C(5)-(5) 28.79(5) (4)-C(5)-(3) 24.97(5) (5)-C(5)-(3) 06.24(3) (5)-C(6)-C(9) 02.3(3) (5)-C(6)-C(7) 09.25(4) C(9)-C(6)-C(7).37(5) (5)-C(6)-C(8) 09.84(3) C(9)-C(6)-C(8) 0.43(5) C(7)-C(6)-C(8) 3.25(5) C(6)-C(7)-H(7A) 09.5 C(6)-C(7)-H(7B) 09.5 H(7A)-C(7)-H(7B) 09.5 C(6)-C(7)-H(7C) 09.5 H(7A)-C(7)-H(7C) 09.5 H(7B)-C(7)-H(7C) 09.5 C(6)-C(8)-H(8A) 09.5 C(6)-C(8)-H(8B) 09.5 H(8A)-C(8)-H(8B) 09.5 C(6)-C(8)-H(8C) 09.5 H(8A)-C(8)-H(8C) 09.5 H(8B)-C(8)-H(8C) 09.5 C(6)-C(9)-H(9A) 09.5 C(6)-C(9)-H(9B) 09.5 H(9A)-C(9)-H(9B) 09.5 C(6)-C(9)-H(9C) 09.5 H(9A)-C(9)-H(9C) 09.5 H(9B)-C(9)-H(9C) 09.5 S30
31 Table S5. Selected hydrogen bonds for 5 [Å and ]. D H A d(d H) d(h A) d(d A) <(DHA) ()-H(A)...(6)# (5) 55.4 C(2)-H(2A)...(2) (8) 6.4 C(3)-H(3B)...(2)# (9) 53.2 C(4)-H(4A)...(2) (7) 4.8 (6)-H(6D)...(2)# (8) 2.307(8) 3.045(6) 47.9(4) (5)-H(5D)...(4) 0.857(7) 2.262(6) (7) 24.9(3) (5)-H(5C)...(2)# (8) 2.99(8) 3.04(7) 54.0(4) (5)-H(5C)...(3)# (8) 2.645(7) (5) 27.4(2) (6)-H(6C)...(2) 0.88(7) 2.5(6) (6) 26.0(4) Symmetry transformations used to generate equivalent atoms: # -x+2,-y+2,-z+; #2 x-,y,z; #3 x+,y,z; #4 -x,-y+,-z+ Figure S. A part of the crystal structure of 5 showing the formation of supramolecular D chain and selected H, H and H hydrogen bonds (dashed lines) Figure S2. A part of the crystal structure of 3 showing the formation of supramolecular D chain and selected H, H and C H hydrogen bonds (dashed lines) S3
32 Table S6. Selected hydrogen bonds for 3 [Å and ]. D H A d(d H) d(h A) d(d A) <(DHA) C(2)-H(2A)...(2) (2) 5.9 C(4)-H(4B)...(4)# (2) 66.8 C(7)-H(7B)...(4) (2) 8. C(8)-H(8A)...(4) (2) 5.3 C(9)-H(9C)...(2)# (2) 56.6 (5)-H(5B)...()#3 0.90(2) 2.66(2) (9) 3.9(7) (5)-H(5B)...(2)#3 0.90(2) 2.3(2) 2.997(2) 63.4(9) (6)-H(6B)...(2) 0.88(2) 2.7(2) 2.744(2) 22.9(6) (5)-H(5A)...(4) 0.87(2) 2.25(2) 2.842(2) 24.5(5) (6)-H(6A)...(5)#4 0.88(2) 2.45(2) 3.5(2) 36.9(7) Symmetry transformations used to generate equivalent atoms: # -x+,-y,-z+; #2 -x+2,-y+,-z+; #3 -x,-y,-z+; #4 x+,y,z Figure S3. A part of the crystal structure of 5 showing the formation of supramolecular layers and selected C H non-covalent contacts (dashed lines) Figure S4. A part of the crystal structure of 3 showing the formation of supramolecular layers and selected C H and H non-covalent contacts (dashed lines) S32
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