Synthesis, crystal structure, antiproliferative activities ... · C15-H15···Cg1 #3 2.99 -2.80...

Acta Cryst. (2019). C75, doi:10.1107/S2053229619015687 Supporting information

Volume 75 (2019)

Supporting information for article:

Synthesis, crystal structure, antiproliferative activities and reverse docking studies of eight novel Schiff bases derived from benzil

Xue-Jie Tan, Di Wang, Xiao-Ming Hei, Feng-Cun Yang, Ya-Ling Zhu, Dian-Xiang Xing and Jian-Ping Ma

Acta Cryst. (2019). C75, doi:10.1107/S2053229619015687 Supporting information, sup-1

Table S1. Hydrogen bond geometry of BDHFI in crystal packing (Å, °).

Notation D—H···A D—H H···A D···A D—H···A

a N3—H35···N1i 0.86 2.14 2.948(2) 155.7

C3—H3···N3ii 0.93 2.61 3.320(3) 133.2

Symmetry code: (i) −x+2, y+1/2, −z+1/2; (ii) x, y−1, z.

Table S2. Selected C-H···π interaction geometry of BDHFI (the H-centroid distance (H···Cg), the perpendicular distance of

H to plane I (H-Perp), slipping angles between H···Cg and the normal to the plane I (γ), the C-H···Cg angles (C-H···Cg), the

C-centroid distance (C···Cg), the angles between C-H bond line and plane I (C-H···π)) (Å, °).

Notation C-H···π (plane I) H···Cg H-Perp γ C-H···Cg C···Cg C-H···π

b N6-H36···Cg5 #4 2.41 2.38 9.37 159 3.230(3) 75

C6-H6···Cg4 #1 2.91 2.81 15.41 148 3.732(3) 70

C11-H11···Cg6 #2 2.95 -2.69 24.16 157 3.821(3) 76

C15-H15···Cg1 #3 2.99 -2.80 20.50 110 3.415(2) 32

intra C18-H18···Cg3 2.80 2.73 12.64 159 3.681(2) 72

Ring 1: N5 C22 C17 C16 C23

Ring 3: C2 C3 C4 C5 C6 C7

Ring 4: C9 C10 C11 C12 C13 C14

Ring 5: C17 C18 C19 C20 C21 C22

Ring 6: C26 C27 C28 C29 C30 C31

Symmetry codes :

#1: 2-x,1-y,-z

#2: 1-x,1-y,-z

#3: 2-x,1/2+y,1/2-z

#4: -1+x,y,z

Table S3. Selected π, π –interaction geometry of BDHFI (the centroid-centroid distance (d), the dihedral angles (α), slipping

angles between centroid–centroid distance and the normal to the plane I (β), slipping angles between centroid–centroid

distance and the normal to the plane J (γ), the perpendicular distance of centroid I to plane J (e) and the perpendicular

distance of centroid J to plane I (f)) (Å, °).

Notation π, π –interactions

(I→J)

d α β γ e f

c Cg3 → Cg3 #8 4.1734(18) 0.00(10) 29.1 29.1 3.6478(9) 3.6477(9)

Cg5 → Cg2 #2 4.3563(19) 78.05(12) 6.5 79.8 0.7740(8) 4.3286(10)

Cg5 → Cg1 #1 4.4381(18) 45.63(10) 19.3 50.1 2.8477(8) 4.1875(8)

Cg1 → Cg5 #3 4.4381(18) 45.63(10) 50.1 19.3 4.1875(8) 2.8478(8)

Cg1 → Cg1 #1 5.002(2) 46.54(11) 32.9 74.9 1.3016(8) 4.2017(8)

Cg4 → Cg3 #10 5.008(2) 86.60(11) 6.6 86.9 0.2678(10) 4.9746(9)

Cg1 → Cg2 #2 5.084(2) 77.86(13) 32.1 89.9 0.0059(8) 4.3044(10)

Cg6 → Cg4 #6 5.137(2) 89.19(12) 16.7 77.2 1.1367(10) 4.9189(10)

Cg2 → Cg6 #7 5.155(2) 44.60(14) 44.6 17.6 4.9132(10) 3.6689(11)

Cg6 → Cg2 #5 5.155(2) 44.60(14) 17.6 44.6 3.6688(11) 4.9131(10)

Cg4 → Cg4 #6 5.178(2) 0.03(12) 41.7 41.7 3.8645(10) 3.8645(10)

Cg1 → Cg6 #2 5.324(2) 77.79(12) 14.2 89.3 0.0625(8) 5.1619(10)

Cg2 → Cg4 #6 5.355(2) 88.99(13) 23.2 70.7 1.7671(10) 4.9217(10)

Cg5 → Cg6 #2 5.377(2) 78.01(11) 16.5 81.5 0.7903(8) 5.1559(10)


Cg1 → Cg5 #4 5.429(2) 0.93(10) 57.9 58.8 2.8099(8) 2.8844(8)

Cg5 → Cg1 #9 5.429(2) 0.93(10) 58.8 57.9 2.8843(8) 2.8099(8)

Cg6 → Cg2 #4 5.430(2) 2.12(14) 58.1 60.1 2.7072(11) 2.8719(10)

Cg2 → Cg2 #5 5.467(2) 42.59(14) 27.3 66.3 2.1938(10) 4.8592(10)

Cg2 → Cg5 #3 5.549(2) 86.04(12) 30.8 70.2 1.8795(10) 4.7665(8)

Cg6 → Cg5 #3 5.617(2) 84.66(11) 32.7 63.0 2.5533(10) 4.7282(8)

Cg3 → Cg4 #9 5.667(2) 86.60(11) 46.3 51.9 3.4939(9) 3.9155(10)

Cg4 → Cg3 #4 5.667(2) 86.60(11) 51.9 46.3 3.9155(10) 3.4939

Cg1 → Cg3 #3 5.697(2) 84.85(10) 50.8 58.3 2.9941(8) 3.5974(9)

intra Cg3 → Cg1 5.893(2) 82.86(10) 18.4 87.7 0.2334(9) 5.5907(8)

intra Cg3 → Cg5 5.039(2) 82.98(10) 11.1 87.1 0.2524(9) 4.9436(8)

intra Cg4 → Cg6 5.250(2) 89.18(12) 17.7 74.2 1.4321(10) 5.0012(10)

Ring 1: N5 C22 C17 C16 C23

Ring 2: N6 C31 C26 C25 C32


Ring 4: C9 C10 C11 C12 C13 C14

Ring 5: C17 C18 C19 C20 C21 C22

Ring 6: C26 C27 C28 C29 C30 C31

Symmetry codes :

#1: 2-x,-1/2+y,1/2-z

#2: 1+x,y,z

#3: 2-x,1/2+y,1/2-z

#4: x,1+y,z

#5: 1-x,1/2+y,1/2-z

#6: 1-x,1-y,-z

#7: 1-x,-1/2+y,1/2-z

#8: 2-x,-y,-z

#9: x,-1+y,z

#10: 2-x,1-y,-z

Table S4. Hydrogen bond geometry of BDHAI in crystal packing (Å, °).


a N6—H36···N4i 0.86 2.36 3.1675(19) 156

intra C18—H18···N4 0.93 2.61 3.100(2) 114

intra C27—H27···N2 0.93 2.59 3.0859(19) 114

intra C34—H34C···N1 0.96 2.29 2.712(3) 106

Symmetry code: (i) −x, −y+1, −z+1.

Table S5. Selected C-H···π interaction geometry of BDHAI (the H-centroid distance (H···Cg), the perpendicular distance of

H to plane I (H-Perp), slipping angles between H···Cg and the normal to the plane I (γ), the C-H···Cg angles (C-H···Cg), the

C-centroid distance (C···Cg), the angles between C-H bond line and plane I (C-H···π)) (Å, °).


b N5-H35···Cg3 #1 2.82 -2.55 24.83 173 3.6707(17) 71

C6-H5···Cg4 #2 2.81 2.79 7.13 146 3.623(2) 63

C30-H30···Cg5 #3 2.86 -2.76 15.27 170 3.776(2) 64

C34-H34B···Cg2 #3 2.97 -2.93 8.89 139 3.746(3) 51

intra C27-H27···Cg4 3.00 -2.83 19.36 148 3.8143(18) 77

Ring 2: N6 C31 C26 C25 C32


Ring 4: C9 C10 C11 C12 C13 C14


Ring 5: C17 C18 C19 C20 C21 C22

Symmetry codes :

#1: 1-x,-y,2-z

#2: 1-x,-y,1-z

#3: 2-x,1-y,1-z

#4: 2-x,-y,1-z

Table S6. Selected π, π –interaction geometry of BDHAI (the centroid-centroid distance (d), the dihedral angles (α),

slipping angles between centroid–centroid distance and the normal to the plane I (β), slipping angles between centroid–

centroid distance and the normal to the plane J (γ), the perpendicular distance of centroid I to plane J (e) and the

perpendicular distance of centroid J to plane I (f)) (Å, °).


(I→J)

d α β γ e f

c Cg1 → Cg5 #1 3.7463(11) 2.71(10) 20.3 17.7 3.5689(8) 3.5126(8)

c Cg5 → Cg1 #1 3.7464(11) 2.71(10) 17.7 20.3 3.5126(8) 3.5690(8)

d Cg1 → Cg1 #1 3.7570(12) 0.00(11) 18.2 18.2 3.5682(8) 3.5683(8)

Cg2 → Cg2 #2 4.6980(10) 0.00(10) 47.1 47.1 3.1988(7) 3.1989(7)

Cg5 → Cg5 #1 4.8212(10) 0.00(9) 41.5 41.5 3.6112(8) 3.6112(8)

Cg3 → Cg1 #1 4.8309(10) 70.94(10) 22.3 86.8 0.2711(8) 4.4703(7)

Cg4 → Cg3 #3 4.9014(13) 86.84(10) 8.1 87.1 0.2517(9) 4.8527(8)

Cg2 → Cg3 #4 4.9313(11) 38.92(9) 35.9 58.6 2.5722(7) 3.9924(8)

Cg3 → Cg2 #4 4.9314(12) 38.92(9) 58.6 35.9 3.9924(8) 2.5722(7)

Cg5 → Cg6 #2 5.1816(11) 73.57(9) 19.9 86.7 0.2953(8) 4.8715(7)

Cg1 → Cg4 #5 5.3141(12) 25.21(11) 41.4 58 2.8158(7) 3.9891(10)

Cg4 → Cg1 #6 5.3141(12) 25.21(11) 58 41.4 3.9891(10) 2.8157(7)

Cg6 → Cg5 #7 5.3490(11) 73.57(9) 38.6 63.2 2.4145(7) 4.1827(8)

Cg6 → Cg6 #8 5.3914(10) 0.03(8) 55.8 55.8 3.0266(7) 3.0266(7)

Cg5 → Cg2 #2 5.4416(11) 73.61(10) 40 88 0.1921(8) 4.1707(7)

Cg6 → Cg3 #4 5.4614(11) 41.26(8) 41.7 77.2 1.2101(7) 4.0804(8)

Cg5 → Cg4 #5 5.4628(13) 22.88(10) 43.9 66 2.2216(7) 3.9343(10)

Cg1 → Cg4 #9 5.4932(13) 25.21(11) 48.4 61.4 2.6315(7) 3.6457(10)

Cg1 → Cg2 #2 5.5142(10) 71.03(10) 41.8 74 1.5243(8) 4.1108(7)

Cg2 → Cg4 #10 5.5157(12) 84.26(11) 27.4 62.7 2.5313(7) 4.8967(10)

Cg4 → Cg6 #8 5.5943(11) 84.56(10) 59.4 47.5 3.7792(10) 2.8450(7)

Cg6 → Cg4 #8 5.5942(11) 84.56(10) 47.5 59.4 2.8450(7) 3.7791(10)

Cg1 → Cg6 #2 5.7520(10) 70.96(10) 33.9 75.2 1.4679(8) 4.7752(7)

Cg3 → Cg5 #1 5.7839(11) 72.36(9) 29.7 85.7 0.4319(8) 5.0223(7)

Cg6 → Cg1 #9 5.8188(10) 70.96(10) 42.8 81.1 0.8971(7) 4.2662(8)

intra Cg1 → Cg3 5.6915(11) 70.94(10) 54.6 20.6 5.3265(7) 3.2972(8)

intra Cg3 → Cg1 5.6915(11) 70.94(10) 20.6 54.6 3.2971(8) 5.3266(7)

intra Cg3 → Cg5 5.1809(11) 72.36(9) 22.8 52.1 3.1793(8) 4.7746(7)

intra Cg4 → Cg6 5.1238(12) 84.56(10) 5.2 81.6 0.7525(10) 5.1029(7)

intra Cg5 → Cg3 5.1809(11) 72.36(9) 52.1 22.8 4.7746(7) 3.1793(8)

Ring 1: N5 C22 C17 C16 C23

Ring 2: N6 C31 C26 C25 C32


Ring 4: C9 C10 C11 C12 C13 C14

Ring 5: C17 C18 C19 C20 C21 C22

Ring 6: C26 C27 C28 C29 C30 C31

Symmetry codes :

#1: 1-x,-y,2-z

#2: 2-x,1-y,1-z

#3: 1-x,-y,1-z

#4: 2-x,-y,1-z


#5: x,y,1+z

#6: x,y,-1+z

#7: x,1+y,-1+z

#8: 2-x,1-y,-z

#9: 1-x,1-y,1-z

#10: 1+x,y,z

Table S7. Hydrogen bond geometry of BDHMFI in crystal packing (Å, °).


a C12—H12···N7i 0.93 2.51 3.372 (7) 155

Symmetry code: (i) −x+2, −y, −z+1.

Table S8. Selected C-H···π interaction geometry of BDHMFI (the H-centroid distance (H···Cg), the perpendicular distance

of H to plane I (H-Perp), slipping angles between H···Cg and the normal to the plane I (γ), the C-H···Cg angles (C-H···Cg),

the C-centroid distance (C···Cg), the angles between C-H bond line and plane I (C-H···π)) (Å, °).


C34-H34A···Cg6 #1 2.85 2.85 3.16 137 3.615(3) 47

C34-H34C··· Cg3 #2 2.98 2.95 7.21 143 3.789(3) 60


Ring 6: C26 C27 C28 C29 C30 C31

Symmetry codes :

#1: 1-x,1-y,1-z

#2: 1+x,y,z

Table S9. Selected π, π –interaction geometry of BDHMFI (the centroid-centroid distance (d), the dihedral angles (α),





(I→J)

d α β γ e f

b Cg1→ Cg1 #1 3.4077(12) 0.00(11) 7.8 7.8 3.3761(8) 3.3761(8)

Cg1→ Cg5 #1 4.2253(12) 2.19(11) 37.9 35.8 3.4282(8) 3.3321(9)

Cg5→ Cg1 #1 4.2254(12) 2.19(11) 35.8 37.9 3.3321(9) 3.4282(8)

Cg2→ Cg3 #2 4.3891(13) 9.99(11) 30.6 37.8 3.4665(8) 3.7788(10)

Cg3→ Cg2 #3 4.3892(13) 9.99(11) 37.8 30.6 3.7789(10) 3.4665(8)

Cg2→ Cg6 #4 4.7018(12) 0.93(10) 41.9 41.9 3.4985(8) 3.5019(8)

Cg6→ Cg2 #4 4.7017(12) 0.93(10) 41.9 41.9 3.5019(8) 3.4985(8)

Cg4→ Cg5 #5 4.8069(13) 19.21(11) 38.8 49.8 3.1052(11) 3.7452(9)

Cg5→ Cg4 #6 4.8068(13) 19.21(11) 49.8 38.8 3.7452(9) 3.1052(11)

Cg3→ Cg6 #3 4.9577(13) 10.72(11) 50.6 40 3.7964(10) 3.1483(8)

Cg6→ Cg3 #2 4.9576(13) 10.72(11) 40 50.6 3.1483(8) 3.7963(10)

Cg2→ Cg2 #4 5.0048(11) 0.02(10) 45.9 45.9 3.4842(8) 3.4842(8)

Cg1→ Cg3 #7 5.0913(13) 80.25(11) 22.6 60.3 2.5247(8) 4.7009(10)

Cg4→ Cg6 #3 5.2158(14) 85.55(11) 7 78.6 1.0332(9) 5.1768(9)

Cg2→ Cg4 #8 5.2274(13) 85.24(11) 29.2 60.4 2.5856(8) 4.5634(9)

Cg6→ Cg6 #4 5.3344(12) 0.00(10) 49.3 49.3 3.4814(8) 3.4814(8)

Cg5→ Cg5 #1 5.7791(13) 0.00(10) 53.2 53.2 3.4652(9) 3.4652(9)

Cg3→ Cg5 #9 5.8127(14) 80.95(11) 49.3 50.6 3.6912(10) 3.7871(8)

Cg5→ Cg3 #9 5.8126(14) 80.95(11) 50.6 49.3 3.7871(8) 3.6911(10)

Cg5→ Cg3 #7 5.9718(14) 80.95(11) 39.5 62 2.8077(8) 4.6078(10)

intra Cg4→ Cg3 5.3730(13) 88.76(12) 51 63.4 2.4028(10) 3.3828(10)

Ring 1: N5 C22 C17 C16 C23


Ring 2: N6 C31 C26 C25 C32


Ring 4: C9 C10 C11 C12 C13 C14

Ring 5: C17 C18 C19 C20 C21 C22

Ring 6: C26 C27 C28 C29 C30 C31

Symmetry codes :

#1: 1-x,-y,-z

#2: 1+x,y,z

#3: -1+x,y,z

#4: 1-x,1-y,1-z

#5: x,y,1+z

#6: x,y,-1+z

#7: -x,-y,-z

#8: -x,1-y,1-z

#9: -x,1-y,-z

Table S10. Hydrogen bond geometry of BDHFN in crystal packing (Å, °).


intra C15—H15···N2 0.93 2.27 2.920(5) 126

Table S11. Selected π, π –interaction geometry of BDHFN (the centroid-centroid distance (d), the dihedral angles (α),





(I→J)

d α β γ e f

a Cg1 → Cg2 #1 3.999(2) 21.29(17) 26.5 13.6 3.8874(13) 3.5788(16)

a Cg2 → Cg1 #1 3.999(2) 21.29(17) 13.6 26.5 3.5788(16) 3.8874(13)

Cg1 → Cg3 #1 4.644(3) 24.18(17) 55.4 32.0 3.9379(13) 2.6376(16)

Cg3 → Cg1 #1 4.644(3) 24.18(17) 32 55.4 2.6377(16) 3.9379(13)

Cg3 → Cg2#2 5.155(3) 87.69(18) 21.6 66.8 2.0311(15) 4.7937(15)

Cg2 → Cg2 #3 5.606(3) 0.02(17) 58 58.0 2.9725(15) 2.9726(15)

Cg1 → Cg3 #4 5.614(3) 24.18(17) 53.7 59.4 2.8606(13) 3.3226(16)

Cg3 → Cg1 #5 5.614(3) 24.18(17) 59.4 53.7 3.3227(16) 2.8605(13)

Cg2 → Cg1 #6 5.635(3) 81.52(17) 15.1 71.0 1.8348(16) 5.4404(13)

Cg3 → Cg1 #6 5.875(3) 82.48(17) 23.1 66.6 2.3340(16) 5.4056(13)

Cg3 → Cg3 #7 5.891(3) 85.78(18) 39.1 69.1 2.1061(15) 4.5699(15)

Cg2 → Cg2 #8 5.985(3) 89.52(17) 56.7 38.5 4.6830(15) 3.2900(15)

Cg2 → Cg2 #2 5.985(3) 89.52(17) 38.5 56.7 3.2901(15) 4.6830(15)

Cg1 → Cg3 #9 5.998(3) 82.48(17) 59.8 61.8 2.8335(13) 3.0191(16)

intra Cg1 → Cg3 5.309(3) 82.48(17) 12.5 76.2 1.2703(13) 5.1831(16)

intra Cg1 → Cg1 5.667(3) 79.95(16) 59.9 59.9 2.8446(13) 2.8445(13)


Ring 2: C9 C10 C11 C12 C13 C14

Ring 3: C13 C14 C15 C16 C17 C18

Symmetry codes :

#1: -x,1-y,-z

#2: x,2-y,1/2+z

#3: -x,2-y,-z

#4: -1/2+x,-1/2+y,z

#5: 1/2+x,1/2+y,z

#6: -x,1+y,1/2-z

#7: 1/2-x,-1/2+y,1/2-z


#8: x,2-y,-1/2+z

#9: -1/2+x,3/2-y,-1/2+z

Table S12. Hydrogen bond geometry of BMHFI in crystal packing (Å, °).


a N3—H24···O1i 0.86 2.17 2.927(2) 146

b C3—H3···O1ii 0.93 2.55 3.413(3) 154

Symmetry codes: (i) 1+x,y,z; (ii) 1/2+x,1/2-y,-z.

Table S13. Selected C-H···π interaction geometry of BMHFI (the H-centroid distance (H···Cg), the perpendicular distance




C15-H15···Cg1 #1 2.87 -2.77 15.48 140 3.635(2) 45

C6-H6···Cg3 #3 2.79 -2.78 3.86 148 3.616(3) 60

C19-H19···Cg4 #5 2.93 2.89 9.1 137 3.667(3) 44

Ring 1: N3 C16 C17 C22 C23


Ring 3: C9 C10 C11 C12 C13 C14

Ring 4: C17 C18 C19 C20 C21 C22

#1: 1-x,1/2+y,1/2-z

#2: -x,1/2+y,1/2-z

#3: x,-1+y,z

#4: 1/2+x,1/2-y,-z

#5: -1/2+x,-1/2-y,-z

Table S14. Selected π, π –interaction geometry of BMHFI (the centroid-centroid distance (d), the dihedral angles (α),





(I→J)

d α β γ e f

Cg1 → Cg4 #1 4.6341(12) 52.96(11) 15.5 47.8 3.1114(9) 4.4652(9)

Cg4 → Cg1 #2 4.6341(12) 52.96(11) 47.8 15.5 4.4652(9) 3.1114(9)

Cg1 → Cg4 #3 4.7120(12) 52.96(11) 50.3 22.3 4.3585(9) 3.0091(9)

Cg4 → Cg1 #4 4.7120(12) 52.96(11) 22.3 50.3 3.0091(9) 4.3586(9)

Cg4 → Cg4 #1 4.8646(13) 53.07(10) 23.4 73.4 1.3920(9) 4.4642(9)

Cg3 → Cg2 #5 4.9038(17) 64.93(14) 13.3 74.4 1.3184(14) 4.7728(10)

Cg1 → Cg1 #4 5.0045(12) 52.85(12) 29.6 75 1.2918(9) 4.3523(9)

Cg2 → Cg2 #6 5.0101(16) 59.58(14) 3.6 63.1 2.2635(12) 5.0001(12)

Cg4 → Cg1 #7 5.0392(14) 0.28(11) 52.5 52.6 3.0599(9) 3.0672(9)

Cg1 → Cg4 #8 5.0393(14) 0.28(11) 52.6 52.5 3.0672(9) 3.0599(9)

Cg2 → Cg3 #9 5.3949(18) 79.33(14) 16.5 79.4 0.9965(10) 5.1735(14)

Cg1 → Cg3 #1 5.4662(16) 87.54(13) 51.4 42.4 4.0380(9) 3.4092(14)

Cg3 → Cg1 #2 5.4664(16) 87.54(13) 42.4 51.4 3.4093(14) 4.0380(9)

Cg4 → Cg3 #1 5.8731(17) 87.77(13) 54.2 52.1 3.6061(9) 3.4330(14)

Cg3 → Cg4 #2 5.8733(17) 87.77(13) 52.1 54.2 3.4331(14) 3.6061(9)

Cg2 → Cg3 #10 5.9578(19) 79.33(14) 59.2 64.5 2.5606(10) 3.0464(14)

intra Cg3 → Cg4 5.5044(16) 80.55(13) 19.4 80.4 0.9185(14) 5.1914(9)

Ring 1: N3 C16 C17 C22 C23



Ring 3: C9 C10 C11 C12 C13 C14

Ring 4: C17 C18 C19 C20 C21 C22

Symmetry codes :

#1: 1/2+x,3/2-y,2-z

#2: -1/2+x,3/2-y,2-z

#3: 1/2+x,1/2-y,2-z

#4: -1/2+x,1/2-y,2-z

#5: 1-x,1/2+y,3/2-z

#6: 2-x,1/2+y,3/2-z

#7: -1+x,y,z

#8: 1+x,y,z

#9: x,-1+y,z

#10: 1+x,-1+y,z

Table S15. Hydrogen bond geometry of BMHAI in crystal packing (Å, °).


intra C18-H18···N2 0.93 2.60 3.074(3) 112

Table S16. Selected C-H···π interaction geometry of BMHAI (the H-centroid distance (H···Cg), the perpendicular distance




a C23-H23···Cg4 #2 2.98 -2.96 6.14 126 3.609(3) 38

C10-H10···Cg1 #1 2.90 2.88 5.51 150 3.732(3) 65

Ring 1: N3 C16 C17 C22 C23

Ring 4: C17 C18 C19 C20 C21 C22

#1: -1+x,y,z

#2: 1/2+x,1/2-y,1/4-z

Table S17. Selected π, π –interaction geometry of BMHAI (the centroid-centroid distance (d), the dihedral angles (α),





(I→J)

d α β γ e f

Cg1 → Cg1 #1 4.4694(14) 77.43(14) 18.3 59.4 2.2777(10) 4.2439(10)

Cg1 → Cg1 #2 4.4694(14) 77.43(14) 59.4 18.3 4.2438(10) 2.2776(10)

Cg4 → Cg1 #1 4.5325(16) 76.64(14) 20.6 77.2 1.0013(12) 4.2421(10)

Cg2 → Cg3 #3 4.8203(17) 63.15(14) 58.9 4.5 4.8052(12) 2.4883(12)

Cg3 → Cg2 #4 4.8204(17) 63.15(14) 4.5 58.9 2.4883(12) 4.8053(12)

Cg1 → Cg3 #5 5.0338(16) 72.60(14) 7.9 78.1 1.0395(10) 4.9864(12)

Cg2 → Cg3 #6 5.1231(17) 63.15(14) 11.7 70.1 1.7445(12) 5.0161(12)

Cg2 → Cg3 #7 5.1727(16) 84.48(14) 17.3 70.9 1.6938(12) 4.9382(11)

Cg4 → Cg3 #5 5.2015(17) 72.36(14) 16.2 72.6 1.5569(12) 4.9939(12)

Cg1 → Cg3 #2 5.2277(16) 22.50(14) 43.8 53.7 3.0955(10) 3.7739(12)

Cg3 → Cg1 #1 5.2277(16) 22.50(14) 53.7 43.8 3.7738(12) 3.0955(10)

Cg4 → Cg2 #6 5.6268(15) 13.26(14) 55 62.3 2.6124(12) 3.2271(12)

Cg1 → Cg4 #1 5.8204(16) 76.64(14) 18.5 66.2 2.3494(10) 5.5202(12)

Cg4 → Cg4 #8 5.8777(17) 75.88(14) 57.4 54.3 3.4265(12) 3.1649(12)


Cg4 → Cg4 #9 5.8777(17) 75.88(14) 54.3 57.4 3.1650(12) 3.4266(12)

Cg2 → Cg2 #10 5.9112(18) 67.17(15) 40 40 4.5303(12) 4.5303(12)

Cg2 → Cg2 #3 5.9616(18) 67.17(15) 53.3 60.1 2.9741(12) 3.5647(12)

Cg3 → Cg4 #8 5.9682(15) 21.09(14) 59.2 76.6 1.3856(12) 3.0590(12)

Cg1 → Cg2 #6 5.9707(15) 14.47(14) 57.1 68.7 2.1676(10) 3.2435(12)

intra Cg3 → Cg4 5.0130(17) 72.36(14) 5.1 71.4 1.5976(12) 4.9928(12)

Ring 1: N3 C16 C17 C22 C23


Ring 3: C9 C10 C11 C12 C13 C14

Ring 4: C17 C18 C19 C20 C21 C22

Symmetry codes :

#1: -1/2+x,1/2-y,1/4-z

#2: 1/2+x,1/2-y,1/4-z

#3: 1+y,x,-z

#4: y,-1+x,-z

#5: 1+x,y,z

#6: 1+y,-1+x,-z

#7: x,1+y,z

#8: -1/2+x,-1/2-y,1/4-z

#9: 1/2+x,-1/2-y,1/4-z

#10: y,x,-z

Table S18. Selected C-H···π interaction geometry of BMHMFI (the H-centroid distance (H···Cg), the perpendicular

distance of H to plane I (H-Perp), slipping angles between H···Cg and the normal to the plane I (γ), the C-H···Cg angles (C-

H···Cg), the C-centroid distance (C···Cg), the angles between C-H bond line and plane I (C-H···π)) (Å, °).


a C23-H23···Cg4 #1 2.59 -2.54 10.71 172 3.5126(18) 78

C6-H6···Cg3 #2 2.80 2.80 2.30 157 3.673(3) 66

Ring 4: C17 C18 C19 C20 C21 C22

Ring 3: C9 C10 C11 C12 C13 C14

#1: -x,1/2+y,1/2-z

#2: 1-x,1/2+y,1/2-z

Table S19. Selected π, π –interaction geometry of BMHMFI (the centroid-centroid distance (d), the dihedral angles (α),





(I→J)

d α β γ e f

b Cg1 → Cg4 #1 3.5371(10) 1.29(8) 15.8 14.6 3.4234(7) 3.4031(7)

b Cg4 → Cg1 #1 3.5372(10) 1.29(8) 14.6 15.8 3.4031(7) 3.4234(7)

c Cg4 → Cg4 #1 3.7069(10) 0.00(8) 23.4 23.4 3.4008(7) 3.4008(7)

Cg2 → Cg2 #2 4.2676(17) 0.02(15) 11.3 11.3 4.1853(12) 4.1853(12)

Cg1 → Cg1 #1 4.5321(10) 0.00(9) 41.8 41.8 3.3796(7) 3.3797(7)

Cg4 → Cg1 #3 4.6692(10) 79.19(8) 10.4 89.6 0.0338(7) 4.5922(7)

Cg1 → Cg1 #3 4.7548(9) 77.98(9) 14.8 63.2 2.1414(7) 4.5971(7)

Cg3 → Cg2 #4 4.9993(14) 86.52(13) 11.4 87 0.2630(10) 4.9008(10)

Cg2 → Cg3 #5 5.1696(16) 84.23(13) 20.1 64.1 2.2579(10) 4.8539(10)

Cg1 → Cg4 #6 5.2256(10) 79.19(8) 26.4 74.8 1.3715(7) 4.6788(7)

Cg4 → Cg4 #7 5.2995(10) 0.00(8) 52.6 52.6 3.2207(7) 3.2207(7)

Cg2 → Cg3 #6 5.9983(15) 86.52(13) 49.2 47.9 4.0231(10) 3.9223(10)

Cg3 → Cg2 #8 5.9984(15) 86.52(13) 47.9 49.2 3.9223(10) 4.0230(10)


intra Cg3 → Cg4 5.6574(13) 83.09(10) 21.4 76 1.3714(10) 5.2674(9)

Ring 1: N3 C16 C17 C22 C23


Ring 3: C9 C10 C11 C12 C13 C14

Ring 4: C17 C18 C19 C20 C21 C22

Symmetry codes :

#1: 1-x,1-y,-z

#2: 2-x,1-y,1-z

#3: 1-x,-1/2+y,1/2-z

#4: 2-x,-1/2+y,1/2-z

#5: x,1+y,z

#6: x,1/2-y,1/2+z

#7: 1-x,-y,-z

#8: x,1/2-y,-1/2+z

Table S20. Hydrogen bond geometry of BMHFN in crystal packing (Å, °).


a C5-H5···O1 i 0.93 2.49 3.355(4) 156

intra C22-H22···N2 0.93 2.28 2.930(4) 126

Symmetry codes: (i) 1-x,-1/2+y,3/2-z.

Table S21. Selected π, π –interaction geometry of BMHFN (the centroid-centroid distance (d), the dihedral angles (α),





(I→J)

d α β γ e f

b Cg2···Cg3 #1 3.9462(19) 21.66(15) 24 4.8 3.9323(14) 3.6040(12)

b Cg3···Cg2 #2 3.9462(19) 21.66(15) 4.8 24 3.6040(12) 3.9323(14)

c Cg1···Cg1 #3 4.0842(19) 0.02(15) 22.8 22.8 3.7652(13) 3.7652(13)

d Cg2···Cg5 #1 4.1057(17) 22.46(13) 39.6 17.2 3.9225(14) 3.1620(10)

d Cg5···Cg2 #2 4.1057(17) 22.46(13) 17.2 39.6 3.1620(10) 3.9225(14)

Cg2···Cg4 #1 4.6011(19) 23.24(15) 53.6 30.5 3.9651(14) 2.7298(13)

Cg4···Cg2 #2 4.6011(19) 23.24(15) 30.5 53.6 2.7297(13) 3.9651(14)

Cg3···Cg2 #4 5.2514(19) 79.79(15) 7.3 76.6 1.2153(12) 5.2093(14)

Cg5···Cg2 #4 5.3067(18) 80.75(13) 10.5 73.1 1.5409(10) 5.2174(14)

Cg4···Cg3 #5 5.3148(17) 87.07(14) 27.5 68.8 1.9237(12) 4.7138(12)

Cg1···Cg3 #6 5.4229(19) 23.20(15) 45.2 62 2.5486(13) 3.8232(12)

Cg5···Cg3 #5 5.5629(16) 85.89(12) 32.7 61.4 2.6590(10) 4.6807(12)

Cg4···Cg2 #4 5.623(2) 81.70(15) 23.2 70.5 1.8734(13) 5.1680(14)

Cg1···Cg1 #7 5.7259(19) 73.58(15) 30 63.3 2.5734(13) 4.9604(13)

Cg2···Cg4 #8 5.7779(19) 23.24(15) 52.1 63.9 2.5387(14) 3.5464(13)

Cg4···Cg4 #8 5.7574(19) 89.49(14) 40.9 66.1 2.3292(12) 4.3525(12)

Cg4···Cg5 #8 5.8274(17) 88.30(12) 51.8 65.7 2.4011(12) 3.6003(10)

Cg4···Cg5 #5 5.8806(16) 88.30(12) 21.8 70 2.0117(12) 5.4597(10)

intra Cg1···Cg2 5.7016(19) 78.29(16) 58 62.5 2.6348(13) 3.0209(14)

intra Cg2···Cg4 5.258(2) 81.70(15) 10.6 73.3 1.5136(14) 5.1684(13)


intra Cg2···Cg5 5.8134(18) 80.75(13) 18.9 74 1.6005(14) 5.5008(10)


Ring 2: C9 C10 C11 C12 C13 C14

Ring 3: C16 C17 C18 C19 C20 C21

Ring 4: C20 C21 C22 C23 C24 C25

Ring 5: C16 C17 C18 C19 C20 C21 C22 C23 C24 C25

Symmetry codes :

#1: x,1/2-y,1/2+z

#2: x,1/2-y,-1/2+z

#3: 1-x,-y,1-z

#4: x,1+y,z

#5: x,3/2-y,1/2+z

#6: 1-x,1-y,1-z

#7: 1-x,1/2+y,3/2-z

#8: -x,-1/2+y,1/2-z

Table S22. Rank values of eight Schiff bases when docking with 18 possible targets. Spearman's rank correlation

coefficients (the last two rows) were calculated on the basis of these rank values.

c-Jun N-

terminal

kinase

3(2R9s)

CaM

kinase II

(2VZ6)

Delta

opioid

receptor

(4N6H)

Gonadot

ropin-

releasing

hormone

receptor

(6NBF)

hERG

(3O0U)

Inhibitor

of

apoptosi

s protein

3

(5C3H)

Kinesin-

like

protein 1

(3ZCW)

Mu

opioid

receptor

(4DKL)

Probable

G-

protein

coupled

receptor

88

(5XF1)

BDHFI 2 2 1 3 2 1 1 2 1

BDHAI 1 1 2 2 1 2 7 1 2

BDHMFI 5 5 6 1 7 5 4 3 4

BDHFN 6 3 4 6 4 4 3 4 3

BMHFI 3 4 3 5 5 3 2 5 7

BMHAI 7 6 8 4 3 6 5 8 6

BMHMFI 4 8 5 8 6 7 6 7 5

BMHFN 8 7 7 7 8 8 8 6 8

ρA549 0.67 0.74 0.57 0.71 0.86 0.83 0.48 0.52 0.62

ρ4T1 0.69 0.76 0.55 0.74 0.88 0.81 0.33 0.55 0.60

Table S22 (continued) Rank values of eight Schiff bases when docking with 18 possible targets.


Protein

kinase C

alpha

(4RA4)

Serine/th

reonine-

protein

kinase

AKT2

(3D0E)

Serine/th

reonine-

protein

kinase

PIM1

(1YXT)

Serine/th

reonine-

protein

kinase

PIM2

(4X7Q)

Serine/th

reonine-

protein

kinase

PIM3

(5DWR)

Sigma

opioid

receptor

(6DK0)

Tryptase

beta-1

(4MPU)

Neuroki

nin 2

receptor(

by

homolog

y)

5-HT6

receptor(

by

homolog

y)

BDHFI 2 1 1 4 2 1 3 1 1

BDHAI 1 6 2 1 1 3 1 2 7

BDHMFI 4 7 6 8 8 8 4 4 3

BDHFN 3 8 4 7 7 7 2 3 2

BMHFI 7 3 3 2 5 5 6 5 6

BMHAI 6 5 5 3 3 2 5 8 5

BMHMFI 5 4 8 5 4 4 8 7 8

BMHFN 8 2 7 6 6 6 7 6 4

ρA549 0.60 0.12 0.86 0.62 0.69 0.69 0.62 0.52 0.17

ρ4T1 0.62 0.00 0.83 0.69 0.71 0.64 0.67 0.50 0.02

Table S23. Rank values of eight Schiff bases in MTT assays.

A549 cells growth inhibition, IC50 (μM) 4T1 cells growth inhibition, IC50 (μM)

BDHFI 1 2

BDHAI 2 1

BDHMFI 5 5

BDHFN 6 6

BMHFI 4 4

BMHAI 3 3

BMHMFI 7 7

BMHFN 8 8


Fig. S1. 1H NMR spectrum of BDHFI.

Fig. S2. 13C NMR spectrum of BDHFI.


Fig. S3 1H NMR spectrum of BDHAI.

Fig. S4 13C NMR spectrum of BDHAI.


Fig. S5 1H NMR spectrum of BDHMFI.

Fig. S6 13C NMR spectrum of BDHMFI.


Fig. S7 1H NMR spectrum of BDHFN.

Fig. S8 13C NMR spectrum of BDHFN.


Fig. S9 1H NMR spectrum of BMHFI.

Fig. S10 13C NMR spectrum of BMHFI.


Fig. S11 1H NMR spectrum of BMHAI.

Fig. S12 13C NMR spectrum of BMHAI.


Fig. S13 1H NMR spectrum of BMHMFI.

Fig. S14 13C NMR spectrum of BMHMFI.


Fig. S15 1H NMR spectrum of BMHFN.

Fig. S16 13C NMR spectrum of BMHFN.


Fig. S17 Sequence alignment of human NK2 receptor (in red) with Chain A of Bovine Rhodopsin (in

cyan). Conserved residues and the residues for which the character is conseved are denoted by * and :

respectively.


Fig. S18 Sequence alignment of human 5-HT6 receptor (Chain A) with the β2 adrenergic receptor

template (PDB ID: 4LDE). Secondary structure is indicated as “PSIPRED” mode.

Synthesis, crystal structure, antiproliferative activities ... · C15-H15···Cg1 #3 2.99 -2.80...

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