(Nitrito-κ2O,O′)bis­[tris­(4-methyl­phen­yl)phosphane-κP]silver(I)

Malan, F.P.; Potgieter, K.; Meijboom, R.

doi:10.1107/S2414314622011488

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 7| Part 12| December 2022| x221148

https://doi.org/10.1107/S2414314622011488

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(Nitrito-κ²O,O′)bis[tris(4-methylphenyl)phosphane-κP]silver(I)

Frederick P. Malan,^a Kariska Potgieter ^b and Reinout Meijboom ^b ^*

^aDepartment of Chemistry, University of Pretoria, Lynnwood Road, Hatfield, Pretoria, 0002, South Africa, and ^bDepartment of Chemical Sciences, University of Johannesburg, PO Box 524, Auckland Park, 2006, Johannesburg, South Africa
^*Correspondence e-mail: rmeijboom@uj.ac.za

Edited by M. Weil, Vienna University of Technology, Austria (Received 23 September 2022; accepted 30 November 2022; online 6 December 2022)

The molecular structure of the title compound, [Ag(NO₂)(C₂₁H₂₁P)₂], exhibits a pseudo-tetrahedral coordination around the central Ag^I atom. The compound crystallizes with one molecule in the asymmetric unit in the monoclinic space group P2₁/n with a rather long b axis [33.8752 (2) Å]. Weak C—H⋯O and C—H⋯N interactions consolidate the crystal packing. The nitrite-O atoms each occupy a single position in the coordination geometry.

Keywords: crystal structure; silver(I) complex; p-tolyl phosphine.

CCDC reference: 2223249

Structure description

Silver is oligodynamic as a result of its excellent antimicrobial, antibacterial and anticancer properties (Meijboom et al., 2009 ). Continuous development of phosphine silver(I) complexes has resulted in this class of compounds being evaluated against numerous cancer cell lines (Potgieter et al., 2016 ). In this context, we report another phosphine silver(I) complex with nitrite as a co-ligand.

The molecular structure of the title compound is shown in Fig. 1. The asymmetric unit contains one complex molecule, featuring a central Ag^I atom, two tris-p-tolylphosphine ligands, and one chelating nitrito ligand. Minor differences in the two Ag—P bond lengths are observed [Ag1—P1 = 2.4287 (5) Å; Ag1—P2 = 2.4570 (5) Å]. The nitrito ligand coordinates in a near symmetric fashion with similar bond lengths [Ag1—O1 = 2.4125 (19) Å; Ag1—O2 = 2.4227 (16) Å; N1—O1 = 1.249 (3) Å; N1—O2 = 1.233 (3) Å]. The pseudo-tetrahedral coordination environment exhibited around the Ag^I atom stems from the three coordinating ligands, with corresponding bond angles of P1—Ag1—P2 [124.597 (16)°], P1—Ag1—O1 [116.26 (6)°], P1—Ag1—O2 [125.62 (4)°], P2—Ag1—O1 [107.68 (7)°], and P2—Ag1—O2 [107.83 (4)°]. The bidentate coordination of the nitrito ligand is underpinned by the O1—Ag1—O2 bite angle of 50.80 (7)°. The ipso-aryl carbon atoms of each of the phosphine ligands overlap in a near-staggered fashion when viewed down the P1—Ag1—P2 axis, presumably due to the steric effect of the bulky phosphine ligands. Corresponding torsion angles are P2—Ag1—P1—C1 = 9.90 (7)°, P2—Ag1—P1—C8 = −108.02 (8)°, P2—Ag1—P1—C15 = 128.73 (9)°, P1—Ag1—P2—C22 = −172.57 (7)°, P1—Ag1—P2—C36 = 70.75 (8)°, and P1—Ag1—P2—C29 = −47.35 (7)°. All of the aforementioned bond lengths and angles closely correspond to those of related Ag^I phosphine complexes (Meijboom et al., 2009).

Figure 1
Perspective view of the molecular structure of the title compound showing displacement ellipsoids at the 50% probability level. Hydrogen atoms are omitted for clarity.

The complex packs in three dimensions as ribbons of isolated molecular complexes. The molecular packing is consolidated through weak intermolecular C—H⋯O and C—H⋯N interactions (Fig. 2, Table 1) involving methyl donor groups and the N and O atom of the nitrito ligand as acceptor atoms; π-stacking interactions are not observed.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C28—H28B⋯O2ⁱ	0.98	2.34	3.292 (3)	165
C42—H42B⋯N1ⁱⁱ	0.98	2.52	3.491 (4)	170
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) .

Figure 2
Packing diagram viewed along the a axis indicating two non-classical C—H⋯N and C—H⋯O hydrogen bonds as cyan dotted lines.

Synthesis and crystallization

Tris-p-tolylphosphine (2 mmol) and silver nitrite (1 mmol) were dissolved separately in acetonitrile (10 ml). The two solutions were carefully mixed together and heated to 353 K for approximately 2 h. The solution was left to crystallize, and small clear colourless crystals were obtained.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	[Ag(NO₂)(C₂₁H₂₁P)₂]
M_r	762.57
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	10.8253 (1), 33.8752 (2), 11.3921 (1)
β (°)	116.880 (1)
V (Å³)	3726.22 (6)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	5.43
Crystal size (mm)	0.21 × 0.15 × 0.12

Data collection
Diffractometer	XtaLAB Synergy R, DW system, HyPix
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2022 $[Rigaku OD (2022). CrysAlis PRO. Rigaku Oxford Diffraction, Tokyo, Japan.]$ )
T_min, T_max	0.524, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	46007, 7335, 7025
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.066, 1.03
No. of reflections	7335
No. of parameters	439
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.55
Computer programs: CrysAlis PRO (Rigaku OD, 2022 $[Rigaku OD (2022). CrysAlis PRO. Rigaku Oxford Diffraction, Tokyo, Japan.]$ ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 2223249

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314622011488/wm4174sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314622011488/wm4174Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314622011488/wm4174Isup3.cdx

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2022); cell refinement: CrysAlis PRO (Rigaku OD, 2022); data reduction: CrysAlis PRO (Rigaku OD, 2022); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

(Nitrito-κ²O,O')bis[tris(4-methylphenyl)phosphane-κP]silver(I) top

Crystal data top

[Ag(NO₂)(C₂₁H₂₁P)₂]	F(000) = 1576
M_r = 762.57	D_x = 1.359 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
a = 10.8253 (1) Å	Cell parameters from 37839 reflections
b = 33.8752 (2) Å	θ = 2.6–78.9°
c = 11.3921 (1) Å	µ = 5.43 mm⁻¹
β = 116.880 (1)°	T = 150 K
V = 3726.22 (6) Å³	Block, colourless
Z = 4	0.21 × 0.15 × 0.12 mm

Data collection top

XtaLAB Synergy R, DW system, HyPix diffractometer	7335 independent reflections
Radiation source: Rotating-anode X-ray tube, Rigaku (Cu) X-ray Source	7025 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.037
Detector resolution: 10.0000 pixels mm^-1	θ_max = 72.1°, θ_min = 2.6°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2022)	k = −33→41
T_min = 0.524, T_max = 1.000	l = −13→14
46007 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.026	H-atom parameters constrained
wR(F²) = 0.066	w = 1/[σ²(F_o²) + (0.0325P)² + 2.634P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.002
7335 reflections	Δρ_max = 0.45 e Å⁻³
439 parameters	Δρ_min = −0.55 e Å⁻³
0 restraints

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	0.65533 (2)	0.63978 (2)	0.42841 (2)	0.02180 (5)
P1	0.77595 (5)	0.57779 (2)	0.44820 (5)	0.02163 (10)
P2	0.65036 (5)	0.69483 (2)	0.28591 (4)	0.01930 (10)
O2	0.57699 (19)	0.66458 (5)	0.58283 (16)	0.0448 (4)
C29	0.81563 (18)	0.70936 (5)	0.29381 (18)	0.0199 (4)
C2	1.0300 (2)	0.57988 (6)	0.43210 (18)	0.0244 (4)
H2	1.0744	0.5726	0.5224	0.029*
C25	0.44352 (19)	0.80859 (5)	0.34053 (19)	0.0235 (4)
C1	0.8860 (2)	0.58141 (5)	0.36531 (18)	0.0220 (4)
C36	0.54431 (19)	0.68106 (5)	0.11468 (18)	0.0210 (4)
C26	0.52576 (19)	0.78451 (6)	0.44557 (19)	0.0244 (4)
H26	0.5396	0.7912	0.5316	0.029*
C22	0.57132 (18)	0.74079 (5)	0.30246 (18)	0.0204 (4)
C37	0.5988 (2)	0.67381 (6)	0.02701 (19)	0.0252 (4)
H37	0.6954	0.6768	0.0553	0.030*
C27	0.58811 (19)	0.75088 (6)	0.42752 (18)	0.0228 (4)
H27	0.6426	0.7346	0.5007	0.027*
C15	0.8942 (2)	0.55952 (6)	0.61134 (18)	0.0228 (4)
C23	0.49327 (19)	0.76552 (5)	0.19701 (18)	0.0223 (4)
H23	0.4833	0.7596	0.1117	0.027*
C3	1.1093 (2)	0.58891 (6)	0.3678 (2)	0.0281 (4)
H3	1.2075	0.5882	0.4153	0.034*
C8	0.6598 (2)	0.53656 (6)	0.37059 (19)	0.0255 (4)
C24	0.42994 (19)	0.79888 (5)	0.21635 (19)	0.0245 (4)
H24	0.3764	0.8154	0.1435	0.029*
C40	0.3180 (2)	0.66502 (6)	−0.0583 (2)	0.0295 (4)
H40	0.2212	0.6624	−0.0871	0.035*
C39	0.3715 (2)	0.65788 (6)	−0.14628 (19)	0.0257 (4)
C30	0.93294 (19)	0.68737 (6)	0.37074 (18)	0.0235 (4)
H30	0.9262	0.6656	0.4202	0.028*
C34	0.8276 (2)	0.74140 (6)	0.2224 (2)	0.0283 (4)
H34	0.7484	0.7568	0.1699	0.034*
O1	0.4291 (2)	0.63526 (8)	0.4201 (2)	0.0757 (7)
C38	0.5131 (2)	0.66231 (6)	−0.10136 (19)	0.0279 (4)
H38	0.5522	0.6574	−0.1597	0.033*
C5	0.9032 (2)	0.59927 (6)	0.16815 (19)	0.0288 (4)
H5	0.8589	0.6050	0.0767	0.035*
C31	1.0598 (2)	0.69698 (6)	0.37583 (19)	0.0285 (4)
H31	1.1391	0.6816	0.4282	0.034*
C4	1.0474 (2)	0.59896 (6)	0.2356 (2)	0.0277 (4)
C16	0.9020 (2)	0.52008 (6)	0.6477 (2)	0.0289 (4)
H16	0.8397	0.5015	0.5877	0.035*
C9	0.5328 (2)	0.53614 (6)	0.3729 (2)	0.0296 (4)
H9	0.5054	0.5582	0.4072	0.035*
C20	0.9859 (2)	0.58611 (6)	0.7025 (2)	0.0298 (4)
H20	0.9801	0.6134	0.6810	0.036*
C41	0.4026 (2)	0.67585 (6)	0.0705 (2)	0.0286 (4)
H41	0.3637	0.6798	0.1295	0.034*
N1	0.4549 (3)	0.65427 (8)	0.5226 (3)	0.0564 (6)
C6	0.8232 (2)	0.59131 (6)	0.23182 (19)	0.0270 (4)
H6	0.7251	0.5926	0.1845	0.032*
C32	1.0722 (2)	0.72882 (6)	0.30523 (19)	0.0276 (4)
C33	0.9545 (2)	0.75080 (6)	0.2280 (2)	0.0302 (4)
H33	0.9614	0.7725	0.1786	0.036*
C28	0.3653 (2)	0.84282 (6)	0.3593 (2)	0.0340 (5)
H28A	0.3499	0.8380	0.4365	0.051*
H28B	0.2759	0.8456	0.2811	0.051*
H28C	0.4193	0.8671	0.3725	0.051*
C19	1.0855 (2)	0.57326 (7)	0.8241 (2)	0.0352 (5)
H19	1.1491	0.5917	0.8837	0.042*
C17	0.9994 (2)	0.50771 (6)	0.7705 (2)	0.0349 (5)
H17	1.0019	0.4807	0.7941	0.042*
C18	1.0939 (2)	0.53389 (7)	0.8601 (2)	0.0353 (5)
C10	0.4457 (2)	0.50374 (7)	0.3256 (2)	0.0355 (5)
H10	0.3595	0.5038	0.3287	0.043*
C13	0.6959 (2)	0.50441 (6)	0.3161 (2)	0.0363 (5)
H13	0.7814	0.5045	0.3116	0.044*
C11	0.4816 (2)	0.47134 (7)	0.2740 (2)	0.0381 (5)
C42	0.2782 (2)	0.64668 (7)	−0.2869 (2)	0.0362 (5)
H42A	0.2573	0.6184	−0.2918	0.054*
H42B	0.3248	0.6525	−0.3414	0.054*
H42C	0.1920	0.6618	−0.3191	0.054*
C12	0.6074 (3)	0.47235 (7)	0.2686 (3)	0.0424 (6)
H12	0.6332	0.4506	0.2316	0.051*
C35	1.2110 (2)	0.73985 (9)	0.3151 (3)	0.0476 (6)
H35A	1.2694	0.7508	0.4025	0.071*
H35B	1.1987	0.7596	0.2478	0.071*
H35C	1.2555	0.7163	0.3013	0.071*
C7	1.1342 (3)	0.60951 (8)	0.1673 (2)	0.0437 (6)
H7A	1.1357	0.6382	0.1581	0.066*
H7B	1.0944	0.5973	0.0799	0.066*
H7C	1.2289	0.5998	0.2194	0.066*
C21	1.2034 (3)	0.51936 (9)	0.9912 (2)	0.0580 (8)
H21A	1.2733	0.5400	1.0327	0.087*
H21B	1.2477	0.4957	0.9779	0.087*
H21C	1.1605	0.5129	1.0483	0.087*
C14	0.3882 (3)	0.43554 (8)	0.2267 (3)	0.0555 (7)
H14A	0.4229	0.4150	0.2944	0.083*
H14B	0.3873	0.4255	0.1456	0.083*
H14C	0.2940	0.4429	0.2095	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.02209 (8)	0.02094 (8)	0.02489 (8)	0.00118 (5)	0.01282 (6)	0.00266 (5)
P1	0.0233 (2)	0.0191 (2)	0.0242 (2)	0.00116 (17)	0.01238 (19)	0.00274 (18)
P2	0.0196 (2)	0.0189 (2)	0.0222 (2)	0.00115 (17)	0.01191 (18)	0.00183 (17)
O2	0.0480 (10)	0.0589 (11)	0.0329 (8)	0.0042 (8)	0.0229 (8)	−0.0024 (8)
C29	0.0199 (9)	0.0200 (9)	0.0224 (9)	−0.0014 (7)	0.0118 (7)	−0.0016 (7)
C2	0.0266 (10)	0.0256 (9)	0.0213 (9)	0.0021 (8)	0.0111 (8)	0.0004 (7)
C25	0.0188 (9)	0.0212 (9)	0.0323 (10)	−0.0035 (7)	0.0132 (8)	−0.0059 (8)
C1	0.0275 (10)	0.0165 (8)	0.0245 (9)	−0.0008 (7)	0.0138 (8)	0.0010 (7)
C36	0.0220 (9)	0.0174 (8)	0.0257 (9)	0.0015 (7)	0.0127 (7)	0.0003 (7)
C26	0.0240 (9)	0.0279 (10)	0.0244 (9)	−0.0057 (8)	0.0136 (8)	−0.0070 (8)
C22	0.0191 (8)	0.0200 (8)	0.0246 (9)	−0.0016 (7)	0.0122 (7)	−0.0004 (7)
C37	0.0200 (9)	0.0309 (10)	0.0266 (9)	0.0010 (8)	0.0122 (8)	0.0008 (8)
C27	0.0208 (9)	0.0252 (9)	0.0217 (9)	−0.0007 (7)	0.0090 (7)	0.0013 (7)
C15	0.0266 (9)	0.0226 (9)	0.0242 (9)	0.0033 (7)	0.0159 (8)	0.0027 (7)
C23	0.0232 (9)	0.0227 (9)	0.0218 (9)	0.0002 (7)	0.0110 (7)	−0.0012 (7)
C3	0.0244 (10)	0.0321 (10)	0.0294 (10)	−0.0012 (8)	0.0135 (8)	−0.0037 (8)
C8	0.0257 (10)	0.0237 (9)	0.0247 (9)	−0.0002 (8)	0.0092 (8)	0.0050 (8)
C24	0.0215 (9)	0.0219 (9)	0.0268 (9)	0.0006 (7)	0.0080 (8)	0.0012 (8)
C40	0.0211 (9)	0.0313 (10)	0.0376 (11)	−0.0043 (8)	0.0146 (8)	−0.0090 (9)
C39	0.0263 (10)	0.0223 (9)	0.0271 (10)	0.0007 (8)	0.0109 (8)	0.0000 (8)
C30	0.0240 (9)	0.0236 (9)	0.0221 (9)	−0.0014 (7)	0.0097 (7)	0.0007 (7)
C34	0.0275 (10)	0.0262 (10)	0.0335 (10)	0.0028 (8)	0.0158 (9)	0.0065 (8)
O1	0.0377 (11)	0.115 (2)	0.0844 (16)	−0.0280 (11)	0.0367 (11)	−0.0450 (14)
C38	0.0269 (10)	0.0365 (11)	0.0251 (9)	0.0011 (8)	0.0161 (8)	−0.0007 (8)
C5	0.0337 (11)	0.0295 (10)	0.0233 (9)	0.0013 (8)	0.0129 (8)	0.0045 (8)
C31	0.0196 (9)	0.0351 (11)	0.0270 (10)	−0.0014 (8)	0.0072 (8)	−0.0012 (8)
C4	0.0323 (10)	0.0267 (10)	0.0288 (10)	−0.0008 (8)	0.0181 (9)	−0.0005 (8)
C16	0.0308 (10)	0.0232 (10)	0.0322 (10)	0.0007 (8)	0.0136 (9)	0.0020 (8)
C9	0.0288 (10)	0.0321 (11)	0.0273 (10)	−0.0008 (8)	0.0122 (8)	0.0022 (8)
C20	0.0424 (12)	0.0231 (9)	0.0270 (10)	0.0003 (9)	0.0184 (9)	0.0008 (8)
C41	0.0257 (10)	0.0333 (11)	0.0346 (11)	−0.0049 (8)	0.0204 (9)	−0.0093 (9)
N1	0.0489 (14)	0.0755 (16)	0.0647 (15)	0.0005 (12)	0.0433 (13)	−0.0034 (13)
C6	0.0251 (10)	0.0264 (10)	0.0278 (10)	0.0028 (8)	0.0105 (8)	0.0047 (8)
C32	0.0242 (10)	0.0360 (11)	0.0248 (9)	−0.0096 (8)	0.0131 (8)	−0.0076 (8)
C33	0.0334 (11)	0.0292 (10)	0.0325 (10)	−0.0077 (8)	0.0190 (9)	0.0020 (8)
C28	0.0311 (11)	0.0299 (11)	0.0424 (12)	0.0019 (9)	0.0178 (10)	−0.0084 (9)
C19	0.0447 (13)	0.0350 (11)	0.0239 (10)	−0.0020 (10)	0.0137 (9)	−0.0046 (9)
C17	0.0446 (13)	0.0241 (10)	0.0355 (11)	0.0077 (9)	0.0177 (10)	0.0082 (9)
C18	0.0436 (13)	0.0370 (12)	0.0246 (10)	0.0112 (10)	0.0148 (9)	0.0044 (9)
C10	0.0299 (11)	0.0410 (12)	0.0326 (11)	−0.0093 (9)	0.0113 (9)	0.0036 (9)
C13	0.0369 (12)	0.0287 (11)	0.0441 (13)	−0.0004 (9)	0.0191 (10)	−0.0040 (9)
C11	0.0394 (12)	0.0309 (11)	0.0314 (11)	−0.0084 (9)	0.0050 (9)	0.0056 (9)
C42	0.0310 (11)	0.0465 (13)	0.0287 (11)	−0.0027 (10)	0.0113 (9)	−0.0041 (9)
C12	0.0467 (14)	0.0279 (11)	0.0485 (14)	−0.0021 (10)	0.0178 (11)	−0.0062 (10)
C35	0.0282 (12)	0.0679 (17)	0.0473 (14)	−0.0169 (11)	0.0176 (11)	−0.0008 (12)
C7	0.0408 (13)	0.0611 (16)	0.0385 (12)	−0.0009 (12)	0.0261 (11)	0.0052 (11)
C21	0.0705 (19)	0.0537 (16)	0.0314 (13)	0.0160 (14)	0.0069 (13)	0.0056 (12)
C14	0.0536 (16)	0.0370 (13)	0.0582 (16)	−0.0176 (12)	0.0096 (13)	−0.0002 (12)

Geometric parameters (Å, º) top

Ag1—O1	2.4125 (19)	C38—H38	0.9500
Ag1—O2	2.4227 (16)	C5—C6	1.384 (3)
Ag1—P1	2.4287 (5)	C5—C4	1.394 (3)
Ag1—P2	2.4570 (5)	C5—H5	0.9500
P1—C8	1.819 (2)	C31—C32	1.388 (3)
P1—C15	1.8234 (19)	C31—H31	0.9500
P1—C1	1.8282 (19)	C4—C7	1.510 (3)
P2—C29	1.8182 (18)	C16—C17	1.382 (3)
P2—C36	1.8209 (19)	C16—H16	0.9500
P2—C22	1.8269 (19)	C9—C10	1.387 (3)
O1—N1	1.249 (3)	C9—H9	0.9500
O2—N1	1.233 (3)	C20—C19	1.386 (3)
C29—C30	1.389 (3)	C20—H20	0.9500
C29—C34	1.397 (3)	C41—H41	0.9500
C2—C3	1.392 (3)	C6—H6	0.9500
C2—C1	1.392 (3)	C32—C33	1.392 (3)
C2—H2	0.9500	C32—C35	1.503 (3)
C25—C26	1.388 (3)	C33—H33	0.9500
C25—C24	1.394 (3)	C28—H28A	0.9800
C25—C28	1.507 (3)	C28—H28B	0.9800
C1—C6	1.397 (3)	C28—H28C	0.9800
C36—C37	1.392 (3)	C19—C18	1.386 (3)
C36—C41	1.392 (3)	C19—H19	0.9500
C26—C27	1.386 (3)	C17—C18	1.390 (3)
C26—H26	0.9500	C17—H17	0.9500
C22—C23	1.393 (3)	C18—C21	1.510 (3)
C22—C27	1.395 (3)	C10—C11	1.381 (3)
C37—C38	1.387 (3)	C10—H10	0.9500
C37—H37	0.9500	C13—C12	1.386 (3)
C27—H27	0.9500	C13—H13	0.9500
C15—C16	1.390 (3)	C11—C12	1.391 (4)
C15—C20	1.394 (3)	C11—C14	1.513 (3)
C23—C24	1.390 (3)	C42—H42A	0.9800
C23—H23	0.9500	C42—H42B	0.9800
C3—C4	1.385 (3)	C42—H42C	0.9800
C3—H3	0.9500	C12—H12	0.9500
C8—C9	1.387 (3)	C35—H35A	0.9800
C8—C13	1.394 (3)	C35—H35B	0.9800
C24—H24	0.9500	C35—H35C	0.9800
C40—C41	1.382 (3)	C7—H7A	0.9800
C40—C39	1.387 (3)	C7—H7B	0.9800
C40—H40	0.9500	C7—H7C	0.9800
C39—C38	1.388 (3)	C21—H21A	0.9800
C39—C42	1.506 (3)	C21—H21B	0.9800
C30—C31	1.387 (3)	C21—H21C	0.9800
C30—H30	0.9500	C14—H14A	0.9800
C34—C33	1.383 (3)	C14—H14B	0.9800
C34—H34	0.9500	C14—H14C	0.9800
O1—N1	1.249 (3)

O1—Ag1—O2	50.80 (7)	C3—C4—C5	118.19 (18)
O1—Ag1—P1	116.26 (6)	C3—C4—C7	120.69 (19)
O2—Ag1—P1	125.62 (4)	C5—C4—C7	121.11 (19)
O1—Ag1—P2	107.68 (7)	C17—C16—C15	120.6 (2)
O2—Ag1—P2	107.83 (4)	C17—C16—H16	119.7
P1—Ag1—P2	124.597 (16)	C15—C16—H16	119.7
C8—P1—C15	104.32 (9)	C8—C9—C10	120.4 (2)
C8—P1—C1	105.61 (9)	C8—C9—H9	119.8
C15—P1—C1	103.18 (9)	C10—C9—H9	119.8
C8—P1—Ag1	113.22 (7)	C19—C20—C15	120.78 (19)
C15—P1—Ag1	119.24 (6)	C19—C20—H20	119.6
C1—P1—Ag1	110.03 (6)	C15—C20—H20	119.6
C29—P2—C36	104.60 (8)	C40—C41—C36	120.68 (18)
C29—P2—C22	105.10 (8)	C40—C41—H41	119.7
C36—P2—C22	103.35 (8)	C36—C41—H41	119.7
C29—P2—Ag1	116.47 (6)	O2—N1—O1	113.4 (2)
C36—P2—Ag1	109.17 (6)	C5—C6—C1	120.37 (19)
C22—P2—Ag1	116.74 (6)	C5—C6—H6	119.8
N1—O2—Ag1	97.86 (14)	C1—C6—H6	119.8
C30—C29—C34	119.00 (17)	C31—C32—C33	118.79 (18)
C30—C29—P2	118.98 (14)	C31—C32—C35	120.3 (2)
C34—C29—P2	122.00 (14)	C33—C32—C35	120.9 (2)
C3—C2—C1	120.60 (18)	C34—C33—C32	120.79 (19)
C3—C2—H2	119.7	C34—C33—H33	119.6
C1—C2—H2	119.7	C32—C33—H33	119.6
C26—C25—C24	117.94 (17)	C25—C28—H28A	109.5
C26—C25—C28	120.83 (18)	C25—C28—H28B	109.5
C24—C25—C28	121.15 (18)	H28A—C28—H28B	109.5
C2—C1—C6	118.49 (17)	C25—C28—H28C	109.5
C2—C1—P1	123.02 (14)	H28A—C28—H28C	109.5
C6—C1—P1	117.95 (15)	H28B—C28—H28C	109.5
C37—C36—C41	118.24 (17)	C20—C19—C18	121.0 (2)
C37—C36—P2	123.18 (14)	C20—C19—H19	119.5
C41—C36—P2	118.52 (14)	C18—C19—H19	119.5
C27—C26—C25	121.38 (17)	C16—C17—C18	121.4 (2)
C27—C26—H26	119.3	C16—C17—H17	119.3
C25—C26—H26	119.3	C18—C17—H17	119.3
C23—C22—C27	118.79 (17)	C19—C18—C17	117.9 (2)
C23—C22—P2	123.59 (14)	C19—C18—C21	121.6 (2)
C27—C22—P2	117.61 (14)	C17—C18—C21	120.5 (2)
C38—C37—C36	120.51 (18)	C11—C10—C9	121.4 (2)
C38—C37—H37	119.7	C11—C10—H10	119.3
C36—C37—H37	119.7	C9—C10—H10	119.3
C26—C27—C22	120.37 (17)	C12—C13—C8	120.2 (2)
C26—C27—H27	119.8	C12—C13—H13	119.9
C22—C27—H27	119.8	C8—C13—H13	119.9
C16—C15—C20	118.18 (18)	C10—C11—C12	117.9 (2)
C16—C15—P1	123.38 (15)	C10—C11—C14	121.1 (2)
C20—C15—P1	118.37 (14)	C12—C11—C14	120.9 (2)
C24—C23—C22	120.16 (17)	C39—C42—H42A	109.5
C24—C23—H23	119.9	C39—C42—H42B	109.5
C22—C23—H23	119.9	H42A—C42—H42B	109.5
C4—C3—C2	121.01 (19)	C39—C42—H42C	109.5
C4—C3—H3	119.5	H42A—C42—H42C	109.5
C2—C3—H3	119.5	H42B—C42—H42C	109.5
C9—C8—C13	118.70 (19)	C13—C12—C11	121.3 (2)
C9—C8—P1	118.16 (15)	C13—C12—H12	119.4
C13—C8—P1	123.03 (16)	C11—C12—H12	119.4
C23—C24—C25	121.30 (18)	C32—C35—H35A	109.5
C23—C24—H24	119.4	C32—C35—H35B	109.5
C25—C24—H24	119.4	H35A—C35—H35B	109.5
C41—C40—C39	121.37 (18)	C32—C35—H35C	109.5
C41—C40—H40	119.3	H35A—C35—H35C	109.5
C39—C40—H40	119.3	H35B—C35—H35C	109.5
C40—C39—C38	117.86 (18)	C4—C7—H7A	109.5
C40—C39—C42	120.99 (19)	C4—C7—H7B	109.5
C38—C39—C42	121.14 (18)	H7A—C7—H7B	109.5
C31—C30—C29	120.40 (18)	C4—C7—H7C	109.5
C31—C30—H30	119.8	H7A—C7—H7C	109.5
C29—C30—H30	119.8	H7B—C7—H7C	109.5
C33—C34—C29	120.26 (19)	C18—C21—H21A	109.5
C33—C34—H34	119.9	C18—C21—H21B	109.5
C29—C34—H34	119.9	H21A—C21—H21B	109.5
N1—O1—Ag1	97.87 (15)	C18—C21—H21C	109.5
C37—C38—C39	121.31 (18)	H21A—C21—H21C	109.5
C37—C38—H38	119.3	H21B—C21—H21C	109.5
C39—C38—H38	119.3	C11—C14—H14A	109.5
C6—C5—C4	121.28 (18)	C11—C14—H14B	109.5
C6—C5—H5	119.4	H14A—C14—H14B	109.5
C4—C5—H5	119.4	C11—C14—H14C	109.5
C30—C31—C32	120.75 (19)	H14A—C14—H14C	109.5
C30—C31—H31	119.6	H14B—C14—H14C	109.5
C32—C31—H31	119.6

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28B···O2ⁱ	0.98	2.34	3.292 (3)	165
C42—H42B···N1ⁱⁱ	0.98	2.52	3.491 (4)	170

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

Acknowledgements

We greatly acknowledge the National Research Foundation (NRF, SA), the University of Pretoria and the University of Johannesburg for funding provided.

Funding information

Funding for this research was provided by: National Research Foundation (grant No. 138280).

References

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