Coordination of a triazine ligand with CuII and AgI investigated by spectral, structural, theoretical and docking studies

Marandi, F.; Moeini, K.; Krautscheid, H.

doi:10.1107/S2053229619011719

Coordination of a triazine ligand with Cu^II and Ag^I investigated by spectral, structural, theoretical and docking studies

F. Marandi, K. Moeini and H. Krautscheid

Two complexes of 5-phenyl-3-(pyridin-2-yl)-1,2,4-triazine (PPTA), namely (ethanol-κO)bis(nitrato-κO)[5-phenyl-3-(pyridin-2-yl-κN)-1,2,4-triazine-κN²]copper(II), [Cu(NO₃)₂(C₁₄H₁₀N₄)(C₂H₆O)] or [Cu(NO₃)₂(PPTA)(EtOH)] (1), and bis[μ-5-phenyl-3-(pyridin-2-yl)-1,2,4-triazine]-κ³N¹:N²,N³;κ³N²,N³:N¹-bis[(nitrato-κO)silver(I)], [Ag₂(NO₃)₂(C₁₄H₁₀N₄)₂] or [Ag₂(NO₃)₂(μ-PPTA)₂] (2), were prepared and characterized by elemental analysis, FT–IR spectroscopy and single-crystal X-ray diffraction. The X-ray structure analysis of 1 revealed a copper complex with square-pyramdial geometry containing two O-donor nitrate ligands along with an N,N′-donor PPTA ligand and one O-donor ethanol ligand. In the binuclear structure of 2, formed by the bridging of two PPTA ligands, each Ag atom has an AgN₃O environment and square-planar geometry. In addition to the four dative interactions, each Ag atom interacts with two O atoms of two nitrate ligands on adjacent complexes to complete a pseudo-octahedral geometry. Density functional theory (DFT) calculations revealed that the geometry around the Cu and Ag atoms in 1^opt and 2^opt (opt is optimized) for an isolated molecule is the same as the experimental results. In 1, O—H

O hydrogen bonds form R₁²(4) motifs. In the crystal network of the complexes, in addition to the hydrogen bonds, there are π–π stacking interactions between the aromatic rings (phenyl, pyridine and triazine) of the ligands on adjacent complexes. The ability of the ligand and complexes 1 and 2 to interact with ten selected biomacromolecules (BRAF kinase, CatB, DNA gyrase, HDAC7, rHA, RNR, TrxR, TS, Top II and B-DNA) was investigated by docking studies. The results show that the studied compounds can interact with proteins better than doxorubicin (except for TrxR and Top II).

Keywords: triazine; copper; silver; crystal structure; DFT calculations; docking studies.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619011719/lf3098sup1.cif Contains datablocks sv0120, sv0187, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619011719/lf3098sv0120sup2.hkl Contains datablock sv0120
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619011719/lf3098sv0187sup3.hkl Contains datablock sv0187

CCDC references: 1887083; 1887082

Computing details top

For both structures, data collection: X-AREA (Stoe & Cie, 2016); cell refinement: X-AREA (Stoe & Cie, 2016); data reduction: X-AREA (Stoe & Cie, 2016); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015). Molecular graphics: ORTEP-3 (Farrugia, 2012), ORTEPIII (Burnett & Johnson, 1996) and DIAMOND (Bergerhoff et al., 1996) for sv0120; ORTEP-3 (Farrugia, 2012), ORTEPIII (Burnett & Johnson, 1996) and DIAMOND (Bergerhoff, et al., 1996) for sv0187. For both structures, software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

(Ethanol-κO)bis(nitrato-κO)[5-phenyl-3-(pyridin-2-yl-κN)-1,2,4-triazine-κN²]copper(II) (sv0120) top

Crystal data top

[Cu(NO₃)₂(C₁₄H₁₀N₄)(C₂H₆O)]	F(000) = 956
M_r = 467.89	D_x = 1.627 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54186 Å
a = 18.8929 (4) Å	Cell parameters from 20318 reflections
b = 12.8744 (2) Å	θ = 4.2–70.7°
c = 8.4047 (2) Å	µ = 2.11 mm⁻¹
β = 110.904 (2)°	T = 180 K
V = 1909.76 (7) Å³	Block, green
Z = 4	0.25 × 0.18 × 0.13 mm

Data collection top

Stoe Stadivari diffractometer	3519 reflections with I > 2σ(I)
Radiation source: GeniX 3D HF Cu	R_int = 0.012
ω scans	θ_max = 70.2°, θ_min = 4.3°
Absorption correction: multi-scan (LANA; Koziskova et al., 2016)	h = −22→22
T_min = 0.443, T_max = 0.909	k = −15→11
22502 measured reflections	l = −9→10
3564 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.078	w = 1/[σ²(F_o²) + (0.0346P)² + 1.5566P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max = 0.001
3564 reflections	Δρ_max = 0.59 e Å⁻³
277 parameters	Δρ_min = −0.33 e Å⁻³
0 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00030 (8)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Data were collected at 180 K using a Stoe StadiVari diffractometer equipped with a copper X-ray microsource (Cu Kα radiation) and a Dectris Pilatus 300k detector. Intensity data were collected using ω scans. All data were corrected for Lorentz and polarization effects. Absorption effects were corrected based on numerical absorption corrections, in addition, a scaling correction was applied using Stoe X-Area software. Structures were solved by direct methods (ShelxS) and refined by full-matrix least-squares against F² by using ShelxL (Sheldrick, 2008). Diagrams of the molecular structure and unit cell were created using Ortep-III and Diamond (Farrugia, 1997, Burnett & Johnson, 1996)(Bergerhof et al., 1996). Crystallographic data and details of the data collection and structure refinement are listed in Table 1, selected bond lengths and angles in Table 2 and hydrogen bond geometries in Table 3.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.64705 (11)	0.81082 (15)	0.0835 (2)	0.0286 (4)
H1	0.6909	0.8482	0.0869	0.034*
C2	0.57648 (12)	0.84640 (15)	−0.0205 (3)	0.0317 (4)
H2	0.5720	0.9076	−0.0866	0.038*
C3	0.51282 (11)	0.79177 (16)	−0.0267 (3)	0.0329 (4)
H3	0.4639	0.8154	−0.0961	0.040*
C4	0.52086 (10)	0.70195 (15)	0.0695 (2)	0.0291 (4)
H4	0.4779	0.6622	0.0653	0.035*
C5	0.59277 (10)	0.67196 (13)	0.1714 (2)	0.0230 (4)
C6	0.60741 (10)	0.57897 (14)	0.2810 (2)	0.0224 (3)
C7	0.64396 (11)	0.41872 (15)	0.4815 (3)	0.0299 (4)
H7A	0.6562	0.3600	0.5547	0.036*
C8	0.56656 (10)	0.43869 (14)	0.3853 (2)	0.0237 (4)
C9	0.50393 (10)	0.37283 (14)	0.3911 (2)	0.0244 (4)
C10	0.51667 (11)	0.28573 (15)	0.4968 (2)	0.0293 (4)
H10	0.5668	0.2679	0.5678	0.035*
C11	0.45628 (12)	0.22534 (16)	0.4981 (3)	0.0353 (4)
H11	0.4653	0.1658	0.5693	0.042*
C12	0.38287 (12)	0.25100 (17)	0.3963 (3)	0.0362 (5)
H12	0.3416	0.2095	0.3984	0.043*
C13	0.36978 (11)	0.33728 (16)	0.2916 (3)	0.0339 (4)
H13	0.3194	0.3550	0.2220	0.041*
C14	0.42953 (11)	0.39788 (15)	0.2877 (2)	0.0289 (4)
H14	0.4201	0.4566	0.2147	0.035*
N1	0.65537 (8)	0.72544 (12)	0.17933 (19)	0.0241 (3)
N2	0.68028 (8)	0.56070 (12)	0.37041 (19)	0.0240 (3)
N3	0.69957 (9)	0.47768 (12)	0.4742 (2)	0.0290 (3)
N4	0.54949 (8)	0.52139 (12)	0.28343 (19)	0.0237 (3)
Cu1	0.75252 (2)	0.66284 (2)	0.33301 (3)	0.02318 (10)
N5	0.81044 (9)	0.86450 (12)	0.4174 (2)	0.0270 (3)
O1	0.81917 (7)	0.78373 (10)	0.33616 (17)	0.0283 (3)
O2	0.85819 (8)	0.93415 (11)	0.4465 (2)	0.0392 (3)
O3	0.75443 (8)	0.87134 (12)	0.4600 (2)	0.0403 (4)
N6	0.85967 (9)	0.61392 (13)	0.6347 (2)	0.0317 (4)
O4	0.84207 (7)	0.58606 (10)	0.47811 (16)	0.0274 (3)
O5	0.91350 (9)	0.57154 (14)	0.7429 (2)	0.0512 (4)
O6	0.82087 (10)	0.68236 (13)	0.66779 (19)	0.0449 (4)
O7	0.77363 (8)	0.59575 (12)	0.10796 (18)	0.0296 (3)
H7	0.7575 (15)	0.545 (2)	0.078 (3)	0.038 (7)*
C15	0.84188 (12)	0.61248 (18)	0.0730 (3)	0.0364 (5)
H15A	0.8649	0.6792	0.1246	0.044*
H15B	0.8289	0.6179	−0.0516	0.044*
C16	0.89888 (12)	0.52694 (18)	0.1408 (3)	0.0449 (5)
H16A	0.8772	0.4611	0.0868	0.067*
H16B	0.9121	0.5213	0.2644	0.067*
H16C	0.9445	0.5427	0.1156	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0276 (9)	0.0241 (9)	0.0322 (10)	−0.0040 (7)	0.0085 (8)	0.0041 (7)
C2	0.0354 (11)	0.0248 (9)	0.0311 (10)	0.0002 (8)	0.0072 (8)	0.0067 (7)
C3	0.0261 (10)	0.0327 (10)	0.0344 (10)	0.0026 (8)	0.0039 (8)	0.0080 (8)
C4	0.0211 (9)	0.0303 (10)	0.0333 (10)	−0.0004 (7)	0.0066 (7)	0.0051 (8)
C5	0.0225 (8)	0.0213 (9)	0.0255 (9)	−0.0006 (7)	0.0088 (7)	0.0005 (7)
C6	0.0208 (8)	0.0223 (9)	0.0245 (8)	0.0014 (7)	0.0086 (7)	0.0003 (7)
C7	0.0273 (9)	0.0247 (9)	0.0363 (10)	0.0021 (7)	0.0095 (8)	0.0084 (8)
C8	0.0248 (9)	0.0218 (9)	0.0263 (9)	0.0015 (7)	0.0113 (7)	−0.0002 (7)
C9	0.0259 (9)	0.0237 (9)	0.0260 (9)	0.0001 (7)	0.0120 (7)	0.0002 (7)
C10	0.0277 (10)	0.0283 (10)	0.0330 (10)	0.0024 (7)	0.0121 (8)	0.0055 (8)
C11	0.0384 (11)	0.0310 (10)	0.0397 (11)	−0.0017 (8)	0.0178 (9)	0.0096 (9)
C12	0.0317 (10)	0.0373 (11)	0.0426 (11)	−0.0101 (9)	0.0171 (9)	0.0026 (9)
C13	0.0249 (10)	0.0380 (11)	0.0363 (11)	−0.0022 (8)	0.0079 (8)	0.0036 (8)
C14	0.0275 (9)	0.0288 (10)	0.0300 (9)	0.0001 (7)	0.0095 (8)	0.0049 (7)
N1	0.0213 (7)	0.0233 (7)	0.0268 (7)	−0.0011 (6)	0.0077 (6)	0.0020 (6)
N2	0.0209 (7)	0.0226 (7)	0.0281 (8)	0.0011 (6)	0.0082 (6)	0.0031 (6)
N3	0.0240 (8)	0.0249 (8)	0.0356 (9)	0.0025 (6)	0.0075 (7)	0.0075 (6)
N4	0.0217 (7)	0.0225 (7)	0.0272 (7)	0.0002 (6)	0.0092 (6)	0.0024 (6)
Cu1	0.01790 (15)	0.02240 (16)	0.02813 (16)	−0.00056 (9)	0.00683 (11)	0.00200 (10)
N5	0.0237 (8)	0.0232 (8)	0.0298 (8)	0.0011 (6)	0.0043 (6)	0.0022 (6)
O1	0.0255 (6)	0.0245 (7)	0.0367 (7)	−0.0028 (5)	0.0134 (6)	−0.0038 (5)
O2	0.0358 (8)	0.0275 (7)	0.0482 (9)	−0.0115 (6)	0.0075 (7)	−0.0027 (6)
O3	0.0327 (8)	0.0375 (8)	0.0561 (9)	0.0015 (6)	0.0222 (7)	−0.0077 (7)
N6	0.0288 (8)	0.0335 (9)	0.0295 (8)	0.0024 (7)	0.0063 (7)	−0.0002 (7)
O4	0.0227 (6)	0.0309 (7)	0.0261 (6)	0.0017 (5)	0.0055 (5)	−0.0017 (5)
O5	0.0453 (9)	0.0576 (11)	0.0338 (8)	0.0181 (8)	−0.0065 (7)	−0.0016 (7)
O6	0.0547 (10)	0.0469 (9)	0.0338 (8)	0.0185 (8)	0.0165 (7)	−0.0013 (7)
O7	0.0286 (7)	0.0289 (8)	0.0327 (7)	−0.0031 (6)	0.0124 (6)	−0.0049 (6)
C15	0.0354 (11)	0.0449 (12)	0.0337 (10)	0.0020 (9)	0.0181 (9)	0.0032 (9)
C16	0.0343 (11)	0.0361 (12)	0.0633 (15)	0.0016 (9)	0.0164 (11)	−0.0117 (11)

Geometric parameters (Å, º) top

C1—N1	1.338 (2)	C12—H12	0.9500
C1—C2	1.386 (3)	C13—C14	1.382 (3)
C1—H1	0.9500	C13—H13	0.9500
C2—C3	1.378 (3)	C14—H14	0.9500
C2—H2	0.9500	N1—Cu1	1.9987 (15)
C3—C4	1.388 (3)	N2—N3	1.345 (2)
C3—H3	0.9500	N2—Cu1	1.9993 (15)
C4—C5	1.377 (3)	Cu1—O4	1.9632 (13)
C4—H4	0.9500	Cu1—O1	1.9962 (13)
C5—N1	1.350 (2)	Cu1—O7	2.2407 (14)
C5—C6	1.475 (2)	N5—O2	1.233 (2)
C6—N4	1.328 (2)	N5—O3	1.235 (2)
C6—N2	1.333 (2)	N5—O1	1.286 (2)
C7—N3	1.315 (3)	N6—O5	1.224 (2)
C7—C8	1.419 (3)	N6—O6	1.239 (2)
C7—H7A	0.9500	N6—O4	1.288 (2)
C8—N4	1.332 (2)	O7—C15	1.437 (2)
C8—C9	1.471 (2)	O7—H7	0.73 (3)
C9—C10	1.397 (3)	C15—C16	1.503 (3)
C9—C14	1.401 (3)	C15—H15A	0.9900
C10—C11	1.384 (3)	C15—H15B	0.9900
C10—H10	0.9500	C16—H16A	0.9800
C11—C12	1.385 (3)	C16—H16B	0.9800
C11—H11	0.9500	C16—H16C	0.9800
C12—C13	1.384 (3)

N1—C1—C2	122.08 (17)	C1—N1—C5	118.46 (15)
N1—C1—H1	119.0	C1—N1—Cu1	127.13 (12)
C2—C1—H1	119.0	C5—N1—Cu1	114.39 (12)
C3—C2—C1	119.04 (18)	C6—N2—N3	119.49 (15)
C3—C2—H2	120.5	C6—N2—Cu1	114.88 (12)
C1—C2—H2	120.5	N3—N2—Cu1	125.62 (11)
C2—C3—C4	119.38 (18)	C7—N3—N2	116.92 (15)
C2—C3—H3	120.3	C6—N4—C8	116.38 (15)
C4—C3—H3	120.3	O4—Cu1—O1	89.12 (5)
C5—C4—C3	118.31 (17)	O4—Cu1—N1	173.50 (6)
C5—C4—H4	120.8	O1—Cu1—N1	97.10 (6)
C3—C4—H4	120.8	O4—Cu1—N2	93.24 (6)
N1—C5—C4	122.72 (16)	O1—Cu1—N2	166.79 (6)
N1—C5—C6	114.66 (15)	N1—Cu1—N2	81.13 (6)
C4—C5—C6	122.62 (16)	O4—Cu1—O7	87.53 (5)
N4—C6—N2	125.70 (16)	O1—Cu1—O7	90.59 (5)
N4—C6—C5	119.39 (15)	N1—Cu1—O7	90.51 (6)
N2—C6—C5	114.91 (15)	N2—Cu1—O7	102.49 (6)
N3—C7—C8	123.13 (17)	O2—N5—O3	122.15 (17)
N3—C7—H7A	118.4	O2—N5—O1	118.05 (16)
C8—C7—H7A	118.4	O3—N5—O1	119.78 (15)
N4—C8—C7	118.37 (16)	N5—O1—Cu1	115.95 (11)
N4—C8—C9	117.97 (16)	O5—N6—O6	123.47 (17)
C7—C8—C9	123.66 (16)	O5—N6—O4	118.54 (17)
C10—C9—C14	119.09 (17)	O6—N6—O4	117.99 (15)
C10—C9—C8	121.72 (16)	N6—O4—Cu1	110.22 (11)
C14—C9—C8	119.19 (16)	C15—O7—Cu1	123.89 (13)
C11—C10—C9	120.03 (18)	C15—O7—H7	111 (2)
C11—C10—H10	120.0	Cu1—O7—H7	117 (2)
C9—C10—H10	120.0	O7—C15—C16	112.74 (18)
C10—C11—C12	120.53 (18)	O7—C15—H15A	109.0
C10—C11—H11	119.7	C16—C15—H15A	109.0
C12—C11—H11	119.7	O7—C15—H15B	109.0
C13—C12—C11	119.79 (18)	C16—C15—H15B	109.0
C13—C12—H12	120.1	H15A—C15—H15B	107.8
C11—C12—H12	120.1	C15—C16—H16A	109.5
C14—C13—C12	120.40 (19)	C15—C16—H16B	109.5
C14—C13—H13	119.8	H16A—C16—H16B	109.5
C12—C13—H13	119.8	C15—C16—H16C	109.5
C13—C14—C9	120.15 (18)	H16A—C16—H16C	109.5
C13—C14—H14	119.9	H16B—C16—H16C	109.5
C9—C14—H14	119.9

Bis[µ-5-phenyl-3-(pyridin-2-yl)-1,2,4-triazine]-κ³N¹:N²,N³;N²,N³:N¹-bis[(nitrato-κO)silver(I)] (sv0187) top

Crystal data top

[Ag₂(NO₃)₂(C₁₄H₁₀N₄)₂]	F(000) = 800
M_r = 404.14	D_x = 1.973 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54186 Å
a = 6.1435 (1) Å	Cell parameters from 17682 reflections
b = 16.2987 (4) Å	θ = 3.2–70.4°
c = 13.9126 (3) Å	µ = 12.13 mm⁻¹
β = 102.414 (2)°	T = 180 K
V = 1360.51 (5) Å³	Rod, yellow
Z = 4	0.30 × 0.06 × 0.04 mm

Data collection top

Stoe STADIVARI diffractometer	2175 reflections with I > 2σ(I)
Radiation source: microfocus	R_int = 0.023
ω scans	θ_max = 67.9°, θ_min = 4.2°
Absorption correction: numerical [X-RED32 (Stoe & Cie, 2016) and LANA (Koziskova et al., 2016)	h = −5→7
T_min = 0.065, T_max = 0.208	k = −19→18
14066 measured reflections	l = −16→15
2432 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.061	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0337P)² + 0.7721P] where P = (F_o² + 2F_c²)/3
2432 reflections	(Δ/σ)_max = 0.002
208 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ag1	0.21648 (3)	0.50990 (2)	0.42836 (2)	0.04241 (9)
C1	−0.1653 (4)	0.63295 (16)	0.32500 (19)	0.0318 (5)
H1	−0.2458	0.5830	0.3113	0.038*
C2	−0.2712 (4)	0.70554 (17)	0.29117 (19)	0.0327 (6)
H2	−0.4216	0.7053	0.2556	0.039*
C3	−0.1554 (5)	0.77841 (17)	0.3098 (2)	0.0360 (6)
H3	−0.2244	0.8291	0.2873	0.043*
C4	0.0639 (5)	0.77619 (16)	0.3621 (2)	0.0346 (6)
H4	0.1479	0.8254	0.3752	0.041*
C5	0.1590 (4)	0.70157 (16)	0.39482 (19)	0.0291 (5)
C6	0.3910 (4)	0.69761 (15)	0.45402 (19)	0.0287 (5)
C7	0.7964 (4)	0.68641 (16)	0.55961 (18)	0.0285 (5)
H7	0.9436	0.6828	0.5984	0.034*
C8	0.7006 (4)	0.76379 (16)	0.53618 (19)	0.0298 (5)
C9	0.8196 (4)	0.84045 (16)	0.57079 (19)	0.0312 (6)
C10	1.0486 (4)	0.84146 (17)	0.6121 (2)	0.0352 (6)
H10	1.1333	0.7924	0.6149	0.042*
C11	1.1514 (5)	0.91381 (18)	0.6489 (2)	0.0404 (7)
H11	1.3069	0.9143	0.6765	0.049*
C12	1.0295 (6)	0.98521 (18)	0.6457 (3)	0.0483 (8)
H12	1.1013	1.0348	0.6708	0.058*
C13	0.8021 (6)	0.98474 (18)	0.6057 (3)	0.0521 (8)
H13	0.7178	1.0337	0.6048	0.063*
C14	0.6980 (5)	0.91293 (18)	0.5671 (2)	0.0406 (7)
H14	0.5432	0.9131	0.5380	0.049*
N1	0.0458 (3)	0.62995 (13)	0.37628 (16)	0.0295 (5)
N2	0.4782 (4)	0.62325 (14)	0.47281 (17)	0.0321 (5)
N3	0.6866 (4)	0.61817 (13)	0.52903 (17)	0.0313 (5)
N4	0.4934 (3)	0.76870 (13)	0.48247 (15)	0.0296 (5)
N5	0.3515 (4)	0.59312 (15)	0.67703 (18)	0.0374 (5)
O1	0.3553 (4)	0.66883 (13)	0.6793 (2)	0.0583 (6)
O2	0.5185 (4)	0.55112 (14)	0.71314 (18)	0.0542 (6)
O3A	0.1920 (5)	0.55619 (18)	0.6205 (3)	0.0400 (10)*	0.726 (9)
O3B	0.1548 (15)	0.5681 (5)	0.6709 (8)	0.050 (3)*	0.274 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.03206 (13)	0.02377 (12)	0.06335 (16)	−0.00061 (7)	−0.00759 (9)	0.00302 (9)
C1	0.0283 (14)	0.0297 (13)	0.0350 (14)	−0.0042 (10)	0.0015 (10)	−0.0001 (10)
C2	0.0255 (14)	0.0354 (14)	0.0341 (14)	−0.0005 (10)	0.0001 (10)	0.0009 (11)
C3	0.0356 (16)	0.0288 (14)	0.0395 (15)	0.0023 (11)	−0.0007 (11)	0.0006 (11)
C4	0.0326 (15)	0.0254 (13)	0.0421 (15)	−0.0030 (10)	−0.0002 (11)	−0.0010 (11)
C5	0.0264 (14)	0.0285 (13)	0.0322 (13)	−0.0037 (9)	0.0057 (10)	−0.0037 (10)
C6	0.0246 (14)	0.0270 (13)	0.0340 (13)	−0.0028 (10)	0.0057 (10)	−0.0012 (10)
C7	0.0216 (13)	0.0295 (13)	0.0319 (13)	−0.0013 (9)	0.0000 (10)	−0.0028 (10)
C8	0.0264 (14)	0.0323 (14)	0.0302 (13)	−0.0018 (10)	0.0051 (10)	−0.0006 (10)
C9	0.0321 (15)	0.0281 (14)	0.0309 (13)	−0.0045 (10)	0.0015 (10)	0.0010 (10)
C10	0.0302 (15)	0.0320 (15)	0.0417 (15)	−0.0025 (10)	0.0043 (11)	−0.0019 (11)
C11	0.0301 (16)	0.0403 (16)	0.0470 (17)	−0.0088 (11)	−0.0005 (12)	−0.0024 (13)
C12	0.0474 (19)	0.0279 (15)	0.0587 (19)	−0.0101 (12)	−0.0126 (14)	0.0005 (13)
C13	0.049 (2)	0.0266 (16)	0.069 (2)	−0.0010 (12)	−0.0128 (15)	0.0037 (14)
C14	0.0346 (16)	0.0301 (15)	0.0495 (17)	−0.0013 (11)	−0.0080 (12)	0.0029 (12)
N1	0.0258 (12)	0.0269 (11)	0.0339 (11)	−0.0031 (8)	0.0022 (8)	−0.0002 (9)
N2	0.0232 (11)	0.0301 (12)	0.0401 (13)	−0.0004 (8)	0.0002 (9)	−0.0013 (9)
N3	0.0238 (12)	0.0290 (12)	0.0388 (12)	0.0018 (8)	0.0019 (9)	0.0000 (9)
N4	0.0265 (12)	0.0282 (11)	0.0324 (12)	−0.0012 (8)	0.0023 (9)	−0.0013 (8)
N5	0.0278 (13)	0.0359 (14)	0.0436 (14)	−0.0071 (9)	−0.0033 (10)	0.0046 (10)
O1	0.0455 (14)	0.0330 (13)	0.0866 (18)	0.0020 (9)	−0.0073 (12)	−0.0166 (11)
O2	0.0351 (12)	0.0481 (13)	0.0706 (15)	0.0051 (9)	−0.0082 (10)	0.0136 (11)

Geometric parameters (Å, º) top

Ag1—N3ⁱ	2.216 (2)	C8—C9	1.475 (4)
Ag1—N1	2.264 (2)	C9—C14	1.393 (4)
Ag1—N2	2.440 (2)	C9—C10	1.401 (4)
C1—N1	1.340 (3)	C10—C11	1.383 (4)
C1—C2	1.383 (4)	C11—C12	1.379 (4)
C2—C3	1.380 (4)	C12—C13	1.388 (5)
C3—C4	1.387 (4)	C13—C14	1.386 (4)
C4—C5	1.383 (4)	N2—N3	1.352 (3)
C5—N1	1.355 (3)	N3—Ag1ⁱ	2.216 (2)
C5—C6	1.486 (4)	N5—O1	1.234 (3)
C6—N2	1.328 (3)	N5—O2	1.246 (3)
C6—N4	1.337 (3)	N5—O3B	1.260 (9)
C7—N3	1.323 (3)	N5—O3A	1.269 (4)
C7—C8	1.400 (4)	O3A—O3B	0.806 (10)
C8—N4	1.333 (3)

N3ⁱ—Ag1—N1	168.20 (8)	C11—C12—C13	120.1 (3)
N3ⁱ—Ag1—N2	121.39 (7)	C14—C13—C12	120.1 (3)
N1—Ag1—N2	70.21 (8)	C13—C14—C9	120.2 (3)
N1—C1—C2	122.9 (2)	C1—N1—C5	117.9 (2)
C3—C2—C1	119.1 (3)	C1—N1—Ag1	122.05 (17)
C2—C3—C4	118.7 (3)	C5—N1—Ag1	120.01 (17)
C5—C4—C3	119.3 (2)	C6—N2—N3	117.5 (2)
N1—C5—C4	122.1 (2)	C6—N2—Ag1	115.17 (17)
N1—C5—C6	117.4 (2)	N3—N2—Ag1	126.22 (16)
C4—C5—C6	120.5 (2)	C7—N3—N2	119.2 (2)
N2—C6—N4	126.0 (2)	C7—N3—Ag1ⁱ	128.10 (18)
N2—C6—C5	116.5 (2)	N2—N3—Ag1ⁱ	112.27 (15)
N4—C6—C5	117.4 (2)	C8—N4—C6	116.5 (2)
N3—C7—C8	121.5 (2)	O1—N5—O2	122.0 (2)
N4—C8—C7	119.2 (2)	O1—N5—O3B	109.7 (5)
N4—C8—C9	118.6 (2)	O2—N5—O3B	123.0 (5)
C7—C8—C9	122.2 (2)	O1—N5—O3A	119.9 (3)
C14—C9—C10	119.3 (2)	O2—N5—O3A	116.7 (3)
C14—C9—C8	118.8 (2)	O3B—N5—O3A	37.2 (4)
C10—C9—C8	121.8 (2)	O3B—O3A—N5	70.9 (7)
C11—C10—C9	120.0 (3)	O3A—O3B—N5	72.0 (8)
C12—C11—C10	120.4 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Selected bond lengths (Å) and angles (°) for complexes of 1, 1^opt, 2 and 2^opt with estimated standard deviations in parentheses top

	1	1^opt		2	2^opt
Cu1—N1	1.9987 (15)	2.061	Ag1—N1	2.264 (2)	2.314
Cu1—N2	1.9993 (15)	2.054	Ag1—N2	2.440 (2)	2.508
Cu1—O1	1.9962 (13)	1.994	Ag1—N3ⁱ	2.216 (2)	2.281
Cu1—O4	1.9632 (13)	1.983	Ag1—O3A	2.680 (3)
Cu1—O7	2.2407 (14)	2.297

N1—Cu1—O1	97.10 (6)		N1—Ag1—N2	70.21 (8)
N1—Cu1—O4	173.50 (6)		N1—Ag1—N3ⁱ	168.20 (8)
N1—Cu1—O7	90.51 (6)		N2—Ag1—N3ⁱ	121.39 (7)
N1—Cu1—N2	81.13 (6)		N1—Ag1—O3A	85.56 (8)
N1—Cu1—O6	129.32 (6)		N2—Ag1—O3A	153.95 (8)
O4—Cu1—O6	53.42 (5)		N3ⁱ—Ag1—O3A	82.70 (9)

Symmetry code: (i) -x+1, -y+1, -z+1.

Hydrogen-bond dimensions (Å, °) in complexes of 1 and 2 top

D—H···A	D—H	H···A	D—H···A	D···A
1
C10—H10···O6ⁱ	0.950	2.700	158.5	3.601 (2)
C11—H11···O5ⁱ	0.950	2.575	133.4	3.300 (2)
C12—H12···O3ⁱⁱ	0.951	2.708	155.1	3.592 (3)
C14—H14···O2ⁱⁱⁱ	0.950	2.559	158.2	3.458 (2)
C4—H4···O2ⁱⁱⁱ	0.949	2.458	159.7	3.364 (2)
C2—H2···O5^iv	0.950	2.552	169.5	3.491 (3)
C16—H16A···O3^v	0.980	2.641	131.6	3.372 (3)
C15—H15B···O6^vi	0.989	2.453	161.5	3.406 (3)
O7—H7···O3^v	0.73 (3)	2.26 (3)	161 (3)	2.956 (2)
O7—H7···O2^v	0.73 (3)	2.56 (3)	140 (3)	3.151 (2)

2
C12—H12···O2^vii	0.951	2.552	127.6	3.221 (4)
C3—H3···O2^viii	0.950	2.583	168.5	3.519 (4)
C3—H3···O1^viii	0.950	2.694	120.0	3.275 (4)
C2—H2···O1^viii	0.950	2.567	125.8	3.216 (3)

Symmetry codes: (i) -x+3/2, y-1/2, -z+3/2; (ii) -x+1, -y+1, -z+1; (iii) x-1/2, -y+3/2, z-1/2; (iv) -x+3/2, y+1/2, -z+1/2; (v) -x+3/2, y-1/2, -z+1/2; (vi) x, y, z-1; (vii) x+2, -y+3/2, z+1/2; (viii) -x-1, y+1/2, -z+1/2.

π–π stacking interactions dimensions (Å and °) in complexes 1 and 2 top

	Centroid–centroid distance	Angle between the planes	Type
1	3.597	1.39	Ph···tz
	3.899	1.68	Ph···py
2	3.467	7.65	Ph···tz
	3.762	9.92	Ph···py

The NBO analysis results for the PPTA and complexes 1 and 2. The values are the total of charge on the similar atoms. The values of parentheses show the variation of charge on the atoms after coordination top

C^PPTA

C^EtOH

H^PPTA

H^EtOH

N^py

N2^tz

N3^tz

N4^tz

N^Nitrato

O^Nitrato

O^EtOH

Metal

PPTA

-0.08

–

+0.25

–

-0.42

-0.27

-0.19

-0.43

–

1^opt

-0.04 (+0.04)

-0.35

+0.24 (-0.01)

+0.27

-0.53 (-0.11)

-0.33 (-0.06)

-0.15 (+0.04)

-0.50 (-0.07)

+0.69

-0.46

-0.81

+0.99

2^opt

-0.04 (+0.04)

–

+0.24 (-0.01)

–

-0.57 (-0.15)

-0.33 (-0.06)

-0.31 (-0.12)

-0.51 (-0.08)

+0.69

-0.52

–

+0.73

HOMO and LUMO orbitals for optimized structures of PPTA and complexes 1 and 2 top

	HOMO	LUMO	Total Energy (kcal mol^-1)	HOMO/LUMO Gap (kcal mol^-1)
PPTA	(a)	(b)	-475964.38	95.83
1^opt	(c)	(d)	-1048023.67	69.52
2^opt	(e)	(f)	-1486507.12	60.81

The calculated fitness values for PPTA ligand and complexes 1 and 2 along with doxorubicin top

	B-DNAs/Min	BRAF-Kinase	CatB	DNA-Gyrase	HDAC7	rHA	RNR	TrxR	TS	Top II
PPTA	50.98	42.95	30.71	46.72	47.71	45.62	39.13	48.79	44.85	42.10
Complex 1	61.24	54.49	32.75	54.26	50.36	56.66	45.06	58.23	50.73	50.24
Complex 2	64.99	59.53	25.85	68.03	39.87	62.31	52.28	49.09	58.40	-2.62
Doxorubicin	83.10	54.21	25.95	52.97	50.73	50.10	49.18	66.70	53.34	59.05

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