Di-μ-acetato-bis­{[3-benzyl-1-(2,4,6-tri­methyl­phen­yl)imidazol-2-ylidene]silver(I)}

Jayaraman, S.; Castillo Guel, R.A.; Malek, K.; Arumugam, K.

doi:10.1107/S2414314619010034

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 4| Part 7| July 2019| x191003

https://doi.org/10.1107/S2414314619010034

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Di-μ-acetato-bis{[3-benzyl-1-(2,4,6-trimethylphenyl)imidazol-2-ylidene]silver(I)}

Selvakumar Jayaraman,^a Roberto Alexander Castillo Guel,^a Kotiba Malek ^a and Kuppuswamy Arumugam ^a ^*

^aDepartment of Chemistry, Wright State University, 3640 Colonel Glenn Hwy, Dayton, OH, 45435, USA
^*Correspondence e-mail: kuppuswamy.arumugam@wright.edu

Edited by S. Parkin, University of Kentucky, USA (Received 20 May 2019; accepted 12 July 2019; online 30 July 2019)

The title compound, [Ag₂(C₂H₃O₂)₂(C₁₉H₂₀N₂)₂] (2), was readily synthesized by treatment of 3-benzyl-1-(2,4,6-trimethylphenyl)imidazolium chloride with silver acetate. The solution structure of the complex was analyzed by NMR spectroscopy, while the solid-state structure was confirmed by single-crystal X-ray diffraction studies. Compound 2 crystallizes in the triclinic space group P $[\overline{1}]$ , with a silver-to-carbene bond length (Ag—C_NHC) of 2.084 (3) Å. The molecule resides on an inversion center, so that only half of the molecule is crystallographically unique. The planes defined by the two imidazole rings are parallel to each other, but not coplanar [interplanar distance is 0.662 (19) Å]. The dihedral angles between the imidazole ring and the benzyl and mesityl rings are 77.87 (12) and 72.86 (11)°, respectively. The crystal structure features π–π stacking interactions between the benzylic groups of inversion-related (−x + 1, −y + 1, −z + 1) molecules and C—H⋯π interactions.

Keywords: N-Heterocyclic carbene; silver acetate; binuclear; π-π stacking; inversion center; crystal structure.

CCDC reference: 1940243

Structure description

The quest for new antibacterial drugs with different modes of action is necessary, as evident from recent bacterial outbreaks (Brown & Wright, 2016 ). Silver-based drugs are promising alternatives to current β-lactam drugs because of their higher antibacterial activity with minimal bacterial resistance and non-toxicity in small doses (Morones-Ramirez et al., 2013 ; Clement & Jarrett, 1994 ). However, many silver-based antibacterial drugs release silver ions rapidly, limiting their bioavailability for a longer period of time (Johnson et al., 2017 ). Recently, silver complexes containing N-heterocyclic carbenes (NHC) have become a popular subject of research because of their versatility and they may release silver ions slowly under biological conditions. Moreover, NHCs are highly desired owing to their facile synthetic modifications and strong affinity for transition-metal centers, which ensures the delayed release of silver to the biological system over longer periods of time (Herrmann, 2002 ; Jafarpour et al., 1999 ; Garrison & Youngs, 2005 ; Meng et al., 2019 ). Several silver–NHC complexes have been synthesized and tested against several bacterial strains (gram-positive and gram-negative). In most instances, these complexes displayed outstanding antibacterial activity (Johnson et al., 2017; Liang et al., 2018 ; Patil et al., 2011 ; Sim et al., 2018 ). Recently, our group reported several dual-targeting redox-active N-heterocyclic carbene ligated gold(I) complexes as cancer therapeutic agents (Arambula et al., 2016 ; McCall et al., 2017 ). In a continuation of this effort, we are currently focusing on the development of dual-targeting redox-active N-heterocyclic carbene-ligated silver(I) complexes to combat drug-resistant bacteria strains. In relevance to this context, we prepared the title compound di-μ-acetato-bis[[3-benzyl-1-(2,4,6-trimethylphenyl)imidazol-2-yl]silver(I)] and studied its solid-state structural features. The results related to the synthesis and solid-state structural characterization are presented here.

The title compound was obtained as colorless crystalline needles by diffusing Et₂O into a saturated CH₂Cl₂ solution. The molecular structure of compound 2 is presented in Fig. 1. Compound 2 forms triclinic crystals, space group P $[\overline{1}]$ . The Ag—C_NHC bond distance was found to be 2.084 (3) Å, which falls within the range reported for other Ag^I–NHC complexes (2.056 to 2.094 Å; Patil et al., 2011). The solid-state structure of complex 2 reveals that the molecule resides on an inversion center (½, 1, ½), so that only half of the molecule is crystallographically unique. This arrangement results in a four-membered centrosymmetric ring (two Ag^I and two O atoms) representing each corner of a parallelogram with Ag—O distances of 2.165 (2) and 2.525 (3) Å and O1—Ag—O1ⁱ and Ag—O1—Agⁱ [symmetry code: (i) 1 − x, 2 − y, 1 − z] bond angles of 70.65 (11) and 109.35 (11)°, respectively. The geometry at the silver atom is trigonal planar, but with significant deviation from idealized geometry because of the non-identical nature of the three groups attached to the silver atom. The O1—Ag—C1 bond angle is 127.22 (11)°, while the C1—Ag—O1ⁱ bond angle is 161.35 (12)°. The dihedral angle between the plane of the imidazole ring (C2–N1–C1–N2–C3) and the parallelogram Ag1–O1–Ag1ⁱ–O1ⁱ is 69.71 (12)°. Similarly, the dihedral angles between the plane of the imidazole ring and the planes of the benzyl (C4–C10) and mesityl (C11–C16) rings are 77.87 (12) and 72.86 (11)°, respectively.

Figure 1
Molecular structure of 2, with displacement ellipsoids drawn at the 50% probability level.

The solid-state structure of compound 2 features C—H⋯π and π–π interactions, the parameters related to these interactions are presented in Table 1. Pictorial representations of the C—H⋯π and π–π interactions are presented in Fig. 2. As viewed along the c axis, molecules are interconnected via C—H⋯π interactions to give uni-directional strands, Fig. 2. These strands are held together by intermolecular π–π stacking interactions of inversion-related benzyl groups parallel to the b axis to yield two-dimensional sheets, Fig. 2. These two-dimensional sheets are stacked one over the other and are held in place by weak intersheet C—H⋯O interactions, Fig. 3. Short interactions of mesityl aryl H atoms with carbonyl oxygen, C—H⋯O, and short interactions of mesityl methyl H atoms with carbonyl carbon, C—H⋯C(O), are represented in Fig. 3.

Table 1
Selected short interactions (Å)

H3⋯π_mesityl(2 − x, 1 − y, 2 − z)	2.642
H13⋯O2(x − 1, 1 + y, z)	2.542
O2⋯H2(x − 1, 1 + y, z)	2.376
O2⋯C2(x − 1, 1 + y, z)	3.162 (5)
H17C⋯C20(1 + x, y, z)	2.820
π_benzyl⋯π_benzyl(1 − x, 1 − y, 1 − z)	3.968 (3)

Figure 2
Intermolecular C—H⋯.π interactions and π–π stacking interactions (shown as dotted lines) for compound 2.

Figure 3
Intercalation of two-dimensional sheets via C—H⋯O and C—H⋯C short interactions in complex 2.

A CSD (Groom et al., 2016 ) structure search for the core NHC–Ag–O revealed 35 hits. A few of those results are summarized here. For more information regarding symmetrically and unsymmetrically substituted silver–NHC acetate complexes such as 1-methyl-3-(4-cyanobenzyl)imidazole-2-silver(I)acetate and 1,3-dibenzyl-4,5-diphenylimidazole-2-silver(I) acetate, see: Patil et al., (2011). For silver(I)–N-heterocyclic carbene complexes derived from caffeine, see: Mohamed et al. (2015 ); Kascatan-Nebioglu et al. (2006 ). Bis(thiophene)-substituted silver acetate complexes have been prepared and used as monomers to make electroconducting polymers, for more information, see: Powell et al. (2010 ). For NHC–Ag acetate complexes bearing benzyl groups, see: Patil et al. (2010 ). In scanning the literature, the C_NHC—Ag, Ag—O(Ac), C—N and N—C—N, bond lengths and N—C_NHC—N bond angles were comparable to those of compound 2.

Synthesis and crystallization

A 20 ml scintillation vial with a stir bar was charged with 33 mg (0.1 mmol) of 1–1-(2,4,6-trimethylphenyl)-3-(benzyl)imidazolium chloride (Samantaray et al., 2011 ), compound (1), NaN(SiCH₃)₂ (20 mg, 0.11 mmol) and 5 ml of dry toluene. The resulting mixture was stirred at 298 K for 1 h, which resulted in a yellow solution and a suspended white precipitate. The heterogeneous mixture was filtered through a plug of Celite into a clean 20 ml scintillation vial containing AgOAc (17 mg, 0.1 mmol) in 5 ml of THF. The resulting mixture was stirred at 298 K for 12 h in the dark. The resulting dark-yellow solution was filtered through a plug of Celite and the volatiles were removed under vacuum. The obtained yellow residue was dissolved in a minimum amount of dichloromethane (1 ml) and triturated with 25 ml of hexanes, resulting in a colorless precipitate. The supernatant liquid was decanted and the precipitate was washed with 5 ml of hexane and dried under vacuum for 24 h to yield the title compound, 30.6 mg, 69% yield, IR, 1562 cm⁻¹.

¹H NMR (300 MHz, CDCl₃): δ 7.39–7.30 (m, 5H), 7.08 (s, 1H), 6.95 (s, 2H), 6.93 (s, 1H), 5.43 (s, 2H), 2.32 (s, 3H), 1.99 (s, 9H). ¹³C-NMR (75 MHz, CDCl₃): δ 178.45, 139.43, 135.70, 135.42, 134.73, 129.37, 129.11, 128.58, 127.73, 123.12, 120.89, 55.88, 23.16, 21.04, 17.67. X-ray diffraction quality single crystals were obtained by diffusing diethyl ether into a saturated solution of 2 in CH₂Cl₂.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	[Ag₂(C₂H₃O₂)₂(C₁₉H₂₀N₂)₂]
M_r	886.57
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	183
a, b, c (Å)	9.078 (2), 10.473 (2), 12.236 (3)
α, β, γ (°)	65.065 (6), 77.420 (7), 65.229 (7)
V (Å³)	956.7 (4)
Z	1
Radiation type	Mo Kα
μ (mm⁻¹)	1.07
Crystal size (mm)	0.64 × 0.26 × 0.2

Data collection
Diffractometer	Bruker SMART X2S benchtop
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.783, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	15885, 3354, 2837
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.080, 1.05
No. of reflections	3354
No. of parameters	239
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.78, −0.43
Computer programs: APEX2 and SAINT (Bruker, 2014 ), SHELXT2014 (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), OLEX2 (Dolomanov et al., 2009 ), PLATON (Spek, 2009 ) and Mercury (Macrae et al., 2006 ).

Structural data

CCDC reference: 1940243

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314619010034/pk4026sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619010034/pk4026Isup4.hkl

Scheme 2. DOI: https://doi.org/10.1107/S2414314619010034/pk4026sup5.tif

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: APEX2 (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009), PLATON (Spek, 2009) and Mercury (Macrae et al., 2006).

Di-µ-acetato-bis{[3-benzyl-1-(2,4,6-trimethylphenyl)imidazol-2-\ ylidene]silver(I)} top

Crystal data top

[Ag₂(C₂H₃O₂)₂(C₁₉H₂₀N₂)₂]	Z = 1
M_r = 886.57	F(000) = 452
Triclinic, P1	D_x = 1.539 Mg m⁻³
a = 9.078 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.473 (2) Å	Cell parameters from 3884 reflections
c = 12.236 (3) Å	θ = 2.5–22.8°
α = 65.065 (6)°	µ = 1.07 mm⁻¹
β = 77.420 (7)°	T = 183 K
γ = 65.229 (7)°	Needle, colorless
V = 956.7 (4) Å³	0.64 × 0.26 × 0.2 mm

Data collection top

Bruker SMART X2S benchtop diffractometer	3354 independent reflections
Radiation source: XOS X-beam microfocus source	2837 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	R_int = 0.056
ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −10→10
T_min = 0.783, T_max = 1.000	k = −12→12
15885 measured reflections	l = −14→14

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.080	w = 1/[σ²(F_o²) + (0.0318P)² + 0.9398P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
3354 reflections	Δρ_max = 0.78 e Å⁻³
239 parameters	Δρ_min = −0.43 e Å⁻³

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.

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

	x	y	z	U_iso*/U_eq
Ag1	0.67227 (4)	0.80738 (3)	0.56178 (3)	0.03206 (12)
O1	0.3866 (3)	0.9810 (3)	0.5928 (2)	0.0339 (6)
O2	0.1564 (3)	1.0757 (3)	0.6868 (3)	0.0416 (7)
N1	0.8628 (3)	0.4584 (3)	0.6776 (3)	0.0238 (6)
N2	0.8626 (3)	0.5700 (3)	0.7896 (3)	0.0240 (7)
C1	0.8045 (4)	0.5972 (4)	0.6853 (3)	0.0236 (8)
C4	0.8287 (4)	0.4281 (4)	0.5811 (3)	0.0288 (8)
H4A	0.9266	0.3556	0.5593	0.035*
H4B	0.7985	0.5212	0.5105	0.035*
C5	0.6935 (4)	0.3665 (4)	0.6172 (3)	0.0256 (8)
C6	0.7160 (5)	0.2350 (4)	0.6026 (3)	0.0324 (9)
H6	0.8166	0.1818	0.5741	0.039*
C7	0.5909 (5)	0.1818 (4)	0.6298 (4)	0.0376 (10)
H7	0.6080	0.0943	0.6182	0.045*
C8	0.4421 (5)	0.2568 (4)	0.6736 (3)	0.0354 (9)
H8	0.3585	0.2205	0.6925	0.042*
C9	0.4189 (5)	0.3870 (4)	0.6892 (4)	0.0358 (9)
H9	0.3186	0.4383	0.7194	0.043*
C10	0.5421 (4)	0.4429 (4)	0.6607 (3)	0.0320 (9)
H10	0.5234	0.5318	0.6707	0.038*
C2	0.9553 (4)	0.3484 (4)	0.7744 (3)	0.0308 (9)
H2	1.0077	0.2458	0.7880	0.037*
C3	0.9553 (4)	0.4173 (4)	0.8454 (3)	0.0317 (9)
H3	1.0071	0.3719	0.9175	0.038*
C11	0.8354 (4)	0.6847 (4)	0.8361 (3)	0.0239 (8)
C12	0.9159 (4)	0.7872 (4)	0.7781 (3)	0.0253 (8)
C17	1.0252 (5)	0.7852 (5)	0.6671 (4)	0.0416 (10)
H17A	0.9612	0.8202	0.6000	0.062*
H17B	1.1011	0.6837	0.6802	0.062*
H17C	1.0833	0.8503	0.6502	0.062*
C13	0.8878 (4)	0.8938 (4)	0.8275 (3)	0.0290 (8)
H13	0.9419	0.9610	0.7924	0.035*
C14	0.7822 (4)	0.9036 (4)	0.9272 (3)	0.0277 (8)
C15	0.7065 (4)	0.7999 (4)	0.9809 (3)	0.0292 (8)
H15	0.6363	0.8050	1.0481	0.035*
C16	0.7312 (4)	0.6879 (4)	0.9383 (3)	0.0265 (8)
C19	0.6529 (5)	0.5716 (5)	1.0031 (4)	0.0409 (10)
H19A	0.7295	0.4801	1.0545	0.061*
H19B	0.6200	0.5507	0.9450	0.061*
H19C	0.5596	0.6103	1.0510	0.061*
C18	0.7545 (5)	1.0233 (5)	0.9749 (4)	0.0432 (11)
H18A	0.8551	1.0086	1.0004	0.065*
H18B	0.6768	1.0159	1.0423	0.065*
H18C	0.7138	1.1216	0.9125	0.065*
C20	0.2867 (4)	0.9732 (4)	0.6823 (3)	0.0239 (8)
C21	0.3356 (5)	0.8255 (4)	0.7907 (4)	0.0387 (10)
H21A	0.4238	0.8174	0.8277	0.058*
H21B	0.3692	0.7421	0.7651	0.058*
H21C	0.2447	0.8237	0.8479	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0419 (2)	0.01798 (16)	0.03125 (18)	−0.00692 (13)	−0.01203 (13)	−0.00377 (12)
O1	0.0329 (15)	0.0224 (13)	0.0305 (15)	−0.0037 (12)	−0.0004 (13)	−0.0024 (11)
O2	0.0340 (17)	0.0239 (15)	0.0545 (19)	−0.0078 (13)	0.0107 (14)	−0.0124 (14)
N1	0.0225 (16)	0.0170 (15)	0.0297 (17)	−0.0057 (12)	−0.0006 (13)	−0.0088 (13)
N2	0.0244 (16)	0.0179 (15)	0.0290 (17)	−0.0068 (13)	−0.0062 (13)	−0.0067 (13)
C1	0.0231 (19)	0.0199 (18)	0.0257 (19)	−0.0100 (15)	−0.0027 (15)	−0.0040 (15)
C4	0.032 (2)	0.027 (2)	0.031 (2)	−0.0120 (17)	0.0036 (17)	−0.0157 (17)
C5	0.031 (2)	0.0229 (19)	0.0235 (19)	−0.0097 (16)	−0.0057 (16)	−0.0069 (16)
C6	0.041 (2)	0.025 (2)	0.030 (2)	−0.0099 (18)	−0.0005 (18)	−0.0113 (17)
C7	0.049 (3)	0.028 (2)	0.042 (2)	−0.016 (2)	−0.012 (2)	−0.0131 (19)
C8	0.040 (3)	0.036 (2)	0.032 (2)	−0.020 (2)	−0.0085 (19)	−0.0066 (19)
C9	0.028 (2)	0.037 (2)	0.039 (2)	−0.0090 (18)	−0.0012 (18)	−0.0144 (19)
C10	0.031 (2)	0.027 (2)	0.040 (2)	−0.0072 (18)	−0.0014 (18)	−0.0188 (18)
C2	0.026 (2)	0.0164 (18)	0.043 (2)	−0.0017 (16)	−0.0081 (17)	−0.0081 (17)
C3	0.031 (2)	0.0168 (18)	0.039 (2)	−0.0038 (16)	−0.0178 (18)	−0.0008 (17)
C11	0.0218 (19)	0.0195 (18)	0.029 (2)	−0.0038 (15)	−0.0111 (16)	−0.0071 (15)
C12	0.0222 (19)	0.0215 (18)	0.030 (2)	−0.0077 (15)	−0.0031 (16)	−0.0071 (16)
C17	0.045 (3)	0.041 (2)	0.048 (3)	−0.026 (2)	0.012 (2)	−0.022 (2)
C13	0.030 (2)	0.0222 (19)	0.037 (2)	−0.0132 (16)	−0.0048 (17)	−0.0079 (17)
C14	0.023 (2)	0.0252 (19)	0.032 (2)	−0.0050 (16)	−0.0059 (16)	−0.0093 (17)
C15	0.030 (2)	0.034 (2)	0.0240 (19)	−0.0141 (17)	−0.0051 (16)	−0.0074 (17)
C16	0.026 (2)	0.0251 (19)	0.026 (2)	−0.0101 (16)	−0.0092 (16)	−0.0019 (16)
C19	0.051 (3)	0.042 (2)	0.037 (2)	−0.031 (2)	0.000 (2)	−0.008 (2)
C18	0.044 (3)	0.044 (3)	0.052 (3)	−0.018 (2)	−0.002 (2)	−0.026 (2)
C20	0.029 (2)	0.0200 (19)	0.028 (2)	−0.0118 (17)	0.0016 (17)	−0.0122 (16)
C21	0.045 (3)	0.029 (2)	0.033 (2)	−0.0116 (19)	0.0011 (19)	−0.0067 (18)

Geometric parameters (Å, º) top

Ag1—O1ⁱ	2.165 (2)	C2—C3	1.343 (5)
Ag1—O1	2.525 (3)	C3—H3	0.9300
Ag1—C1	2.084 (3)	C11—C12	1.407 (5)
O1—Ag1ⁱ	2.165 (2)	C11—C16	1.398 (5)
O1—C20	1.258 (4)	C12—C17	1.500 (5)
O2—C20	1.230 (4)	C12—C13	1.392 (5)
N1—C1	1.360 (4)	C17—H17A	0.9600
N1—C4	1.467 (4)	C17—H17B	0.9600
N1—C2	1.381 (4)	C17—H17C	0.9600
N2—C1	1.360 (4)	C13—H13	0.9300
N2—C3	1.390 (4)	C13—C14	1.390 (5)
N2—C11	1.446 (4)	C14—C15	1.382 (5)
C4—H4A	0.9700	C14—C18	1.505 (5)
C4—H4B	0.9700	C15—H15	0.9300
C4—C5	1.518 (5)	C15—C16	1.393 (5)
C5—C6	1.387 (5)	C16—C19	1.511 (5)
C5—C10	1.390 (5)	C19—H19A	0.9600
C6—H6	0.9300	C19—H19B	0.9600
C6—C7	1.386 (5)	C19—H19C	0.9600
C7—H7	0.9300	C18—H18A	0.9600
C7—C8	1.371 (6)	C18—H18B	0.9600
C8—H8	0.9300	C18—H18C	0.9600
C8—C9	1.379 (5)	C20—C21	1.516 (5)
C9—H9	0.9300	C21—H21A	0.9600
C9—C10	1.387 (5)	C21—H21B	0.9600
C10—H10	0.9300	C21—H21C	0.9600
C2—H2	0.9300

Ag1···C1	2.084 (3)	C20···O2	1.230 (4)
Ag1···O1	2.165 (2)	C1···N1	1.360 (4)
O1···C20	1.258 (4)	C2···C3	1.343 (5)

O1ⁱ—Ag1—O1	70.65 (11)	C12—C11—N2	119.1 (3)
C1—Ag1—O1	127.22 (11)	C16—C11—N2	118.4 (3)
C1—Ag1—O1ⁱ	161.35 (12)	C16—C11—C12	122.5 (3)
Ag1ⁱ—O1—Ag1	109.35 (11)	C11—C12—C17	122.3 (3)
C20—O1—Ag1ⁱ	117.5 (2)	C13—C12—C11	116.9 (3)
C20—O1—Ag1	132.6 (2)	C13—C12—C17	120.8 (3)
C1—N1—C4	124.6 (3)	C12—C17—H17A	109.5
C1—N1—C2	111.2 (3)	C12—C17—H17B	109.5
C2—N1—C4	124.1 (3)	C12—C17—H17C	109.5
C1—N2—C3	111.3 (3)	H17A—C17—H17B	109.5
C1—N2—C11	124.8 (3)	H17A—C17—H17C	109.5
C3—N2—C11	123.9 (3)	H17B—C17—H17C	109.5
N1—C1—Ag1	129.0 (2)	C12—C13—H13	118.7
N2—C1—Ag1	126.9 (2)	C14—C13—C12	122.6 (3)
N2—C1—N1	104.0 (3)	C14—C13—H13	118.7
N1—C4—H4A	109.0	C13—C14—C18	120.1 (3)
N1—C4—H4B	109.0	C15—C14—C13	118.1 (3)
N1—C4—C5	112.7 (3)	C15—C14—C18	121.8 (4)
H4A—C4—H4B	107.8	C14—C15—H15	118.7
C5—C4—H4A	109.0	C14—C15—C16	122.6 (4)
C5—C4—H4B	109.0	C16—C15—H15	118.7
C6—C5—C4	120.6 (3)	C11—C16—C19	121.7 (3)
C6—C5—C10	118.1 (3)	C15—C16—C11	117.3 (3)
C10—C5—C4	121.2 (3)	C15—C16—C19	121.0 (3)
C5—C6—H6	119.5	C16—C19—H19A	109.5
C7—C6—C5	121.0 (4)	C16—C19—H19B	109.5
C7—C6—H6	119.5	C16—C19—H19C	109.5
C6—C7—H7	119.6	H19A—C19—H19B	109.5
C8—C7—C6	120.7 (3)	H19A—C19—H19C	109.5
C8—C7—H7	119.6	H19B—C19—H19C	109.5
C7—C8—H8	120.7	C14—C18—H18A	109.5
C7—C8—C9	118.7 (4)	C14—C18—H18B	109.5
C9—C8—H8	120.7	C14—C18—H18C	109.5
C8—C9—H9	119.4	H18A—C18—H18B	109.5
C8—C9—C10	121.3 (4)	H18A—C18—H18C	109.5
C10—C9—H9	119.4	H18B—C18—H18C	109.5
C5—C10—H10	119.9	O1—C20—C21	115.9 (3)
C9—C10—C5	120.2 (3)	O2—C20—O1	124.6 (3)
C9—C10—H10	119.9	O2—C20—C21	119.5 (3)
N1—C2—H2	126.4	C20—C21—H21A	109.5
C3—C2—N1	107.2 (3)	C20—C21—H21B	109.5
C3—C2—H2	126.4	C20—C21—H21C	109.5
N2—C3—H3	126.8	H21A—C21—H21B	109.5
C2—C3—N2	106.4 (3)	H21A—C21—H21C	109.5
C2—C3—H3	126.8	H21B—C21—H21C	109.5

Symmetry code: (i) −x+1, −y+2, −z+1.

Selected short interactions (Å) top

H3···π_mesityl(2 - x, 1 - y, 2 - z)	2.642
H13···O2(x - 1, 1 + y, z)	2.542
O2···H2(x - 1, 1 + y, z)	2.376
O2···C2(x - 1, 1 + y, z)	3.162 (5)
H17C···C20(1 + x, y, z)	2.820
π_benzyl···π_benzyl(1 - x, 1 - y, 1 - z)	3.968 (3)

Acknowledgements

The authors thank Wright State University for instrument infrastructure and Dr David Grossie (Wright State University) for valuable crystallographic discussions.

Funding information

Funding for this research was provided by: National Institute of Health, National Cancer Institute (grant No. CA232765 to Kuppuswamy Arumugam).

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