Fig. 1S. 1H NMR Spectrum of the Free Ligand

Fig. 1S. 1H NMR spectrum of the free ligand.

Fig. 2S. 1H NMR spectrum of Cu(II)-complex.

Fig. 3S. 13CNMR spectrum of Cu(II)-complex.

(A)

(B) (C)

(D) (E)

Fig. 4S. X-Ray diffraction patterns (A, B, C, D and E) of Co(II), Ni(II), Cu(II), Fe(III) and Mn(II) complexes, respectively.

(A)
(B) / (C)
(D) / (E)

Fig. 5S. Scanning electron micrographs of Co(II), Ni(II), Cu(II), Fe(III) and Mn(II) (A, B, C, D and E) inset shows the magnified image.

Fig. 6S. The images for the calculated distribution of activity scores for GPCR ligands, kinase inhibitors, ion channel modulators, nuclear receptor ligands, protease inhibitors and other enzyme targets compared with scores for about 100'000 average drug-like molecules.

(A)

(A)

(B)

(C)

(D)

Fig. 7S. DOS diagrams of ligand, Mn(II), Ni(II) and Cu(II) complexes (A, B, C and D, respectively).

Table 1S. Selected bond lengths (Å) of ligand using DFT-method from DMOL3 calculations

Bond / Length(Å) / Bond / Length(Å) / Bond / Length(Å)
O(32)-H(50) / 0.995 / C(25)-C(26) / 1.405 / C(30)-C(31) / 1.410
C(24)-C(31) / 1.429 / C(24)-C(25) / 1.426 / C(29)-C(30) / 1.417
C(23)-C(28) / 1.429 / C(28)-C(29) / 1.412 / C(27)-O(32) / 1.388
C(23)-C(24) / 1.459 / C(26)-C(27) / 1.414 / C(22)-C(27) / 1.444
C(22)-C(23) / 1.458 / C(21)-C(22) / 1.440 / N(20)-C(21) / 1.338
C(18)-C(19) / 1.407 / C(17)-N(20) / 1.370 / C(17)-C(18) / 1.437
C(16)-C(17) / 1.436 / C(15)-C(16) / 1.404 / C(14)-C(19) / 1.435
C(14)-C(15) / 1.437 / N(13)-C(14) / 1.372 / C(11)-N(13) / 1.338
C(9)-C(10) / 1.414 / C(8)-C(9) / 1.417 / C(5)-C(6) / 1.410
C(7)-C(8) / 1.409 / C(5)-O(12) / 1.381 / C(4)-C(11) / 1.438
C(4)-C(5) / 1.446 / C(3)-C(10) / 1.429 / C(3)-C(4) / 1.464
C(2)-C(7) / 1.433 / C(1)-C(2) / 1.420 / C(1)-C(6) / 1.349

Table 2S. Selected bond angles (°) of ligand using DFT-method from DMOL3 calculations

Angle / Degree(°) / Angle / Degree(°)
C(31)-C(30)-C(29) / 119.405 / C(30)-C(31)-C(24) / 121.710
C(29)-C(28)-C(23) / 121.874 / O(32)-C(27)-C(26) / 120.178
O(32)-C(27)-C(22) / 117.041 / C(26)-C(27)-C(22) / 122.778
C(30)-C(29)-C(28) / 120.155 / C(27)-C(26)-C(25) / 119.590
C(26)-C(25)-C(24) / 120.950 / C(31)-C(24)-C(25) / 121.233
C(22)-C(21)-N(20) / 125.023 / C(31)-C(24)-C(23) / 118.976
C(25)-C(24)-C(23) / 119.787 / C(28)-C(23)-C(24) / 117.818
C(24)-C(23)-C(22) / 119.655 / C(27)-C(22)-C(23) / 117.016
C(28)-C(23)-C(22) / 122.514 / C(27)-C(22)-C(21) / 117.214
C(23)-C(22)-C(21) / 125.707 / C(18)-C(19)-C(14) / 121.601
C(21)-N(20)-C(17) / 125.851 / C(19)-C(18)-C(17) / 120.552
N(20)-C(17)-C(18) / 124.618 / N(20)-C(17)-C(16) / 117.582
C(18)-C(17)-C(16) / 117.799 / C(17)-C(16)-C(15) / 121.589
C(19)-C(14)-N(13) / 117.474 / C(19)-C(14)-C(15) / 117.743
C(14)-N(13)-C(11) / 125.631 / C(15)-C(14)-N(13) / 124.581
C(16)-C(15)-C(14) / 120.640 / N(13)-C(11)-C(4) / 125.881
C(10)-C(9)-C(8) / 120.106 / C(9)-C(10)-C(3) / 122.362
C(11)-C(4)-C(3) / 118.512 / C(11)-C(4)-C(5) / 123.865
C(6)-C(5)-C(4) / 120.574 / O(12)-C(5)-C(4) / 119.910
O(12)-C(5)-C(6) / 119.516 / C(5)-C(6)-C(1) / 121.025
C(6)-C(1)-C(2) / 123.780 / C(3)-C(2)-C(1) / 117.037
C(7)-C(2)-C(1) / 123.624 / C(7)-C(2)-C(3) / 119.320
C(4)-C(3)-C(2) / 119.794 / C(10)-C(3)-C(2) / 116.990

Table 3S. Selected bond lengths (Å) of Mn complex using DFT-method from DMOL3 calculations

Bond / Length(Å) / Bond / Length(Å) / Bond / Length(Å)
N(38)-O(41) / 1.542 / N(38)-O(40) / 1.465 / N(38)-O(39) / 1.487
O(37)-Mn(42) / 2.051 / O(36)-Mn(42) / 1.989 / N(34)-O(37) / 1.535
N(34)-O(36) / 1.469 / N(34)-O(35) / 1.481 / O(41)-Mn(33) / 2.043
Mn(33)-O(40) / 1.983 / O(32)-Mn(33) / 1.998 / C(30)-C(31) / 1.495
C(29)-C(30) / 1.497 / C(28)-C(29) / 1.499 / C(27)-O(32) / 1.498
C(27)-C(26) / 1.497 / C(25)-C(26) / 1.491 / C(31)-C(24) / 1.503
C(24)-C(25) / 1.497 / C(23)-C(28) / 1.507 / C(23)-C(24) / 1.511
C(27)-C(22) / 1.527 / C(22)-C(23) / 1.521 / C(21)-C(22) / 1.527
Mn(33)-N(20) / 2.003 / N(20)-C(21) / 1.478 / C(18)-C(19) / 1.506
C(17)-N(20) / 1.488 / C(17)-C(18) / 1.509 / C(16)-C(17) / 1.496
C(15)-C(16) / 1.492 / C(14)-C(19) / 1.506 / C(14)-C(15) / 1.493
N(13)-Mn(42) / 2.002 / N(13)-C(14) / 1.484 / O(12)-Mn(42) / 1.997
C(11)-N(13) / 1.478 / C(9)-C(10) / 1.499 / C(8)-C(9) / 1.496
C(7)-C(8) / 1.495 / C(5)-O(12) / 1.495 / C(5)-C(6) / 1.497
C(1)-C(2) / 1.497 / C(6)-C(1) / 1.489 / C(2)-C(3) / 1.511
C(2)-C(7) / 1.502 / C(3)-C(4) / 1.522 / C(10)-C(3) / 1.507
C(4)-C(5) / 1.525 / C(4)-C(11) / 1.526

Table 4S. Selected bond angles (°) ofMn complex using DFT-method from DMOL3 calculations

Angle / Degree(°) / Angle / Degree(°)
O(37)-Mn(42)-O(36) / 64.698 / N(13)-Mn(42)-O(12) / 101.797
O(37)-Mn(42)-N(13) / 112.360 / O(36)-Mn(42)-N(13) / 124.710
O(37)-Mn(42)-O(12) / 102.800 / O(36)-Mn(42)-O(12) / 133.394
N(38)-O(41)-Mn(33) / 97.974 / N(38)-O(40)-Mn(33) / 103.381
O(41)-N(38)-O(40) / 92.975 / O(41)-N(38)-O(39) / 108.981
O(40)-N(38)-O(39) / 107.659 / Mn(42)-O(37)-N(34) / 98.620
Mn(42)-O(36)-N(34) / 103.759 / O(37)-N(34)-O(36) / 92.018
O(37)-N(34)-O(35) / 109.234 / O(36)-N(34)-O(35) / 108.664
O(41)-Mn(33)-O(40) / 65.601 / O(41)-Mn(33)-O(32) / 127.455
O(41)-Mn(33)-N(20) / 127.591 / O(40)-Mn(33)-O(32) / 113.500
O(40)-Mn(33)-N(20) / 112.053 / O(32)-Mn(33)-N(20) / 102.343
Mn(33)-O(32)-C(27) / 109.721 / C(30)-C(31)-C(24) / 120.215
C(31)-C(30)-C(29) / 119.639 / C(30)-C(29)-C(28) / 120.417
C(29)-C(28)-C(23) / 120.627 / O(32)-C(27)-C(26) / 115.359
O(32)-C(27)-C(22) / 123.293 / C(26)-C(27)-C(22) / 121.328
C(27)-C(26)-C(25) / 120.270 / C(26)-C(25)-C(24) / 119.901
C(31)-C(24)-C(25) / 118.925 / C(31)-C(24)-C(23) / 120.618
C(25)-C(24)-C(23) / 120.451 / C(28)-C(23)-C(24) / 118.483
C(28)-C(23)-C(22) / 120.959 / C(24)-C(23)-C(22) / 120.509
C(27)-C(22)-C(23) / 117.310 / C(27)-C(22)-C(21) / 124.416
C(23)-C(22)-C(21) / 118.215 / C(22)-C(21)-N(20) / 123.103
Mn(33)-N(20)-C(17) / 123.655 / Mn(33)-N(20)-C(21) / 117.261
C(18)-C(19)-C(14) / 119.994 / C(21)-N(20)-C(17) / 119.046
N(20)-C(17)-C(18) / 122.571 / C(19)-C(18)-C(17) / 120.606
C(14)-N(13)-C(11) / 119.413 / Mn(42)-N(13)-C(11) / 118.173
Mn(42)-N(13)-C(14) / 122.409 / C(15)-C(14)-N(13) / 117.566
C(19)-C(14)-N(13) / 123.597 / C(19)-C(14)-C(15) / 118.837
C(16)-C(15)-C(14) / 120.949 / C(17)-C(16)-C(15) / 120.856
C(18)-C(17)-C(16) / 118.393 / N(20)-C(17)-C(16) / 119.003
C(10)-C(9)-C(8) / 120.343 / C(9)-C(10)-C(3) / 120.734
N(13)-C(11)-C(4) / 123.783 / Mn(42)-O(12)-C(5) / 112.572
C(6)-C(1)-C(2) / 119.785 / C(7)-C(2)-C(1) / 118.877
C(3)-C(2)-C(1) / 120.497 / C(7)-C(2)-C(3) / 120.624
C(4)-C(3)-C(2) / 120.618 / C(10)-C(3)-C(2) / 118.376
C(10)-C(3)-C(4) / 120.989 / C(5)-C(4)-C(3) / 117.138
C(11)-C(4)-C(3) / 118.016 / C(11)-C(4)-C(5) / 124.838
C(6)-C(5)-C(4) / 121.401 / O(12)-C(5)-C(4) / 122.986
O(12)-C(5)-C(6) / 115.556 / C(5)-C(6)-C(1) / 120.324
C(8)-C(7)-C(2) / 120.292 / C(9)-C(8)-C(7) / 119.628

Table 5S. Selected bond lengths (Å) of Ni complex using DFT-method from DMOL3 calculations

Bond / Length(Å) / Bond / Length(Å) / Bond / Length(Å)
C(47)-O(50) / 1.385 / C(47)-O(49) / 1.287 / C(47)-C(48) / 1.495
C(43)-O(46) / 1.377 / C(43)-O(45) / 1.294 / C(43)-C(44) / 1.494
C(39)-O(42) / 1.382 / C(39)-O(41) / 1.290 / C(39)-C(40) / 1.493
C(35)-O(38) / 1.384 / C(35)-O(37) / 1.296 / C(35)-C(36) / 1.493
O(50)-Ni(34) / 3.146 / O(49)-Ni(34) / 2.117 / O(46)-Ni(34) / 3.083
O(45)-Ni(34) / 2.090 / O(37)-Ni(33) / 2.106 / O(41)-Ni(33) / 2.076
O(32)-Ni(34) / 2.407 / C(22)-C(23) / 1.469 / C(27)-C(22) / 1.442
C(30)-C(31) / 1.413 / Ni(33)-O(38) / 3.096 / O(42)-Ni(33) / 3.165
C(27)-O(32) / 1.399 / C(28)-C(29) / 1.419 / C(29)-C(30) / 1.421
C(31)-C(24) / 1.437 / C(25)-C(26) / 1.413 / C(27)-C(26) / 1.419
C(18)-C(19) / 1.417 / N(20)-C(21) / 1.371 / N(20)-Ni(34) / 2.044
C(14)-C(15) / 1.433 / C(14)-C(19) / 1.435 / C(15)-C(16) / 1.415
C(5)-O(12) / 1.383 / C(7)-C(8) / 1.413 / C(8)-C(9) / 1.421
C(4)-C(5) / 1.447 / C(4)-C(11) / 1.442 / C(5)-C(6) / 1.420
C(1)-C(2) / 1.433 / C(6)-C(1) / 1.408 / C(2)-C(3) / 1.457
C(2)-C(7) / 1.433 / C(3)-C(4) / 1.464 / C(10)-C(3) / 1.435
C(16)-C(17) / 1.433 / C(17)-C(18) / 1.435 / C(17)-N(20) / 1.408
C(9)-C(10) / 1.418 / C(11)-N(13) / 1.375 / O(12)-Ni(33) / 3.148
O(12)-H(58) / 0.994 / N(13)-C(14) / 1.425 / N(13)-Ni(33) / 2.068
C(23)-C(24) / 1.459 / C(23)-C(28) / 1.437 / C(24)-C(25) / 1.433
C(21)-C(22) / 1.442

Table 6S. Selected bond angles (°) of Ni complex using DFT-method from DMOL3 calculations

Angle / Degree(°) / Angle / Degree(°)
C(47)-O(50)-Ni(34) / 72.151 / O(50)-C(47)-O(49) / 116.860
C(47)-O(49)-Ni(34) / 123.489 / O(50)-C(47)-C(48) / 119.324
O(49)-C(47)-C(48) / 123.767 / C(43)-O(46)-Ni(34) / 73.166
C(43)-O(45)-Ni(34) / 122.394 / O(46)-C(43)-O(45) / 116.833
O(46)-C(43)-C(44) / 120.299 / O(45)-C(43)-C(44) / 122.741
C(39)-O(42)-Ni(33) / 71.058 / C(39)-O(41)-Ni(33) / 125.539
O(42)-C(39)-O(41) / 117.287 / O(42)-C(39)-C(40) / 119.420
C(35)-O(37)-Ni(33) / 122.318 / C(35)-O(38)-Ni(33) / 73.260
O(38)-C(35)-C(36) / 119.981 / O(38)-C(35)-O(37) / 116.898
O(50)-Ni(34)-N(20) / 115.266 / O(50)-Ni(34)-O(32) / 82.512
O(49)-Ni(34)-O(45) / 104.831 / O(49)-Ni(34)-O(46) / 112.559
O(42)-Ni(33)-O(38) / 87.075 / O(42)-Ni(33)-O(41) / 46.085
O(42)-Ni(33)-N(13) / 134.291 / O(42)-Ni(33)-O(37) / 84.090
O(41)-Ni(33)-O(38) / 131.753 / O(42)-Ni(33)-O(12) / 76.147
C(15)-C(14)-N(13) / 119.147 / N(20)-C(17)-C(16) / 118.615
Ni(33)-N(13)-C(14) / 104.272 / C(19)-C(14)-N(13) / 121.657
O(38)-Ni(33)-O(12) / 66.690 / O(38)-Ni(33)-N(13) / 99.385
O(37)-Ni(33)-O(12) / 111.871 / O(37)-Ni(33)-N(13) / 132.431
O(32)-C(27)-C(26) / 118.780 / N(13)-Ni(33)-O(12) / 65.675
O(12)-C(5)-C(4) / 122.653 / O(12)-C(5)-C(6) / 115.047
N(13)-C(11)-C(4) / 126.103 / Ni(33)-O(12)-C(5) / 98.531
C(14)-N(13)-C(11) / 118.580 / Ni(33)-N(13)-C(11) / 128.432
O(41)-Ni(33)-N(13) / 120.523 / O(41)-Ni(33)-O(37) / 106.369
O(38)-Ni(33)-O(37) / 47.518 / O(41)-Ni(33)-O(12) / 104.289
O(32)-C(27)-C(22) / 118.116 / Ni(34)-O(32)-C(27) / 118.839
Ni(34)-N(20)-C(17) / 112.658 / Ni(34)-N(20)-C(21) / 126.890
N(20)-C(17)-C(18) / 122.480 / C(21)-N(20)-C(17) / 119.780
O(49)-Ni(34)-N(20) / 112.216 / O(49)-Ni(34)-O(32) / 128.394
O(46)-Ni(34)-O(32) / 113.066 / O(46)-Ni(34)-O(45) / 47.564
O(45)-Ni(34)-O(32) / 88.986 / O(46)-Ni(34)-N(20) / 102.476
O(32)-Ni(34)-N(20) / 79.754 / O(45)-Ni(34)-N(20) / 140.054
O(50)-Ni(34)-O(49) / 46.363 / O(37)-C(35)-C(36) / 123.026
O(50)-Ni(34)-O(45) / 100.821 / O(50)-Ni(34)-O(46) / 141.424

Table 7S. Selected bond lengths (Å) of Cu complex using DFT-method from DMOL3 calculations

Bond / Length(Å) / Bond / Length(Å) / Bond / Length(Å)
C(47)-O(50) / 1.391 / C(47)-O(49) / 1.280 / C(43)-O(46) / 1.385
C(43)-O(45) / 1.285 / C(39)-O(42) / 1.380 / C(39)-O(41) / 1.288
C(35)-O(38) / 1.379 / C(35)-O(37) / 1.299 / O(50)-Cu(34) / 3.197
O(49)-Cu(34) / 2.358 / O(46)-Cu(34) / 3.419 / O(45)-Cu(34) / 2.439
O(42)-Cu(33) / 3.193 / O(41)-Cu(33) / 2.120 / Cu(33)-O(38) / 3.311
C(27)-O(32) / 1.378 / O(32)-Cu(34) / 3.339 / O(37)-Cu(33) / 2.090
C(14)-C(19) / 1.435 / N(20)-C(21) / 1.360 / N(20)-Cu(34) / 2.435
N(13)-C(14) / 1.415 / N(13)-Cu(33) / 2.090 / C(14)-C(15) / 1.430
C(5)-O(12) / 1.400 / C(11)-N(13) / 1.367 / O(12)-Cu(33) / 2.421

Table 8S.Selected bond angles (°) of [Ni(H2PAPT)Cl2(H2O)].2H2O using DFT-method from DMOL3 calculations

Angle / Degree(°) / Angle / Degree(°)
C(43)-O(45)-Cu(34) / 121.663 / O(46)-C(43)-O(45) / 121.926
C(47)-O(50)-Cu(34) / 76.793 / O(50)-C(47)-O(49) / 118.096
C(47)-O(49)-Cu(34) / 118.990 / O(50)-C(47)-C(48) / 119.982
O(49)-C(47)-C(48) / 121.903 / C(43)-O(46)-Cu(34) / 73.342
O(46)-C(43)-C(44) / 114.717 / O(45)-C(43)-C(44) / 123.335
C(39)-O(42)-Cu(33) / 71.966 / C(39)-O(41)-Cu(33) / 126.107
O(42)-C(39)-O(41) / 116.654 / O(42)-C(39)-C(40) / 120.131
O(41)-C(39)-C(40) / 122.912 / C(35)-O(38)-Cu(33) / 66.222
C(35)-O(37)-Cu(33) / 125.096 / O(50)-Cu(34)-O(49) / 45.695
O(38)-C(35)-O(37) / 121.286 / O(50)-Cu(34)-O(46) / 74.429
O(38)-C(35)-C(36) / 115.421 / O(50)-Cu(34)-O(45) / 81.509
O(37)-C(35)-C(36) / 123.060 / O(50)-Cu(34)-O(32) / 105.336
O(50)-Cu(34)-N(20) / 143.736 / O(49)-Cu(34)-O(46) / 88.793
O(49)-Cu(34)-O(45) / 119.582 / O(49)-Cu(34)-O(32) / 96.148
O(49)-Cu(34)-N(20) / 99.236 / O(46)-Cu(34)-O(45) / 43.060
O(46)-Cu(34)-O(32) / 172.756 / O(46)-Cu(34)-N(20) / 121.182
O(45)-Cu(34)-O(32) / 129.721 / O(45)-Cu(34)-N(20) / 133.257
O(32)-Cu(34)-N(20) / 63.319 / O(42)-Cu(33)-O(41) / 45.231
O(42)-Cu(33)-O(38) / 78.374 / O(42)-Cu(33)-O(37) / 82.114
O(42)-Cu(33)-N(13) / 156.872 / O(42)-Cu(33)-O(12) / 93.421
O(41)-Cu(33)-O(38) / 89.503 / O(41)-Cu(33)-O(37) / 119.118
O(41)-Cu(33)-N(13) / 113.264 / O(41)-Cu(33)-O(12) / 97.045
O(38)-Cu(33)-O(37) / 44.449 / O(38)-Cu(33)-N(13) / 114.322
O(37)-Cu(33)-N(13) / 120.699 / O(38)-Cu(33)-O(12) / 160.752
O(32)-C(27)-C(26) / 113.679 / Cu(34)-O(32)-C(27) / 123.698
Cu(34)-N(20)-C(21) / 146.149 / O(32)-C(27)-C(22) / 124.335
C(21)-N(20)-C(17) / 117.192 / Cu(34)-N(20)-C(17) / 95.894
N(20)-C(17)-C(16) / 122.894 / N(20)-C(17)-C(18) / 118.683
Cu(33)-N(13)-C(11) / 127.430 / Cu(33)-N(13)-C(14) / 112.400
Cu(33)-O(12)-C(5) / 122.059 / C(14)-N(13)-C(11) / 118.373
O(12)-C(5)-C(4) / 118.607 / N(13)-C(11)-C(4) / 128.546
C(35)-O(37)-Cu(33) / 125.096 / O(50)-Cu(34)-O(49) / 45.695
O(38)-C(35)-O(37) / 121.286 / O(50)-Cu(34)-O(46) / 74.429
O(38)-C(35)-C(36) / 115.421 / O(50)-Cu(34)-O(45) / 81.509
O(37)-C(35)-C(36) / 123.060 / O(50)-Cu(34)-O(32) / 105.336
O(50)-Cu(34)-N(20) / 143.736 / O(49)-Cu(34)-O(46) / 88.793
O(49)-Cu(34)-O(45) / 119.582 / O(49)-Cu(34)-O(32) / 96.148
O(49)-Cu(34)-N(20) / 99.236 / O(46)-Cu(34)-O(45) / 43.060
O(46)-Cu(34)-O(32) / 172.756 / O(46)-Cu(34)-N(20) / 121.182
N(13)-Cu(33)-O(12) / 79.674 / O(37)-Cu(33)-O(12) / 117.629

1