Poly[[μ2-1,2-bis­(diphenyl­phosphan­yl)-1,2-diethylhydrazine]-μ4-nitrato-μ2-nitrato-silver(I)]

Kriel, F.H.; Fernandes, M.A.; Coates, J.

doi:10.1107/S1600536810019094

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page m710

https://doi.org/10.1107/S1600536810019094

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Poly[[μ₂-1,2-bis(diphenylphosphanyl)-1,2-diethylhydrazine]-μ₄-nitrato-μ₂-nitrato-silver(I)]

Frederik H. Kriel,^a ^* Manuel A. Fernandes ^b and Judy Coates ^a

^aProject AuTEK, Mintek, Private Bag X3015, Randburg 2125, South Africa, and ^bMolecular Science Institute, School of Chemistry, University of the Witwatersrand, PO Wits, 2050 Johannesburg, South Africa
^*Correspondence e-mail: erikk@mintek.co.za

(Received 30 April 2010; accepted 21 May 2010; online 26 May 2010)

The title compound, [Ag₂(NO₃)₂(C₂₈H₃₀N₂P₂)]_n, crystallizes in polymeric α-helices. Three O atoms from three different nitrate ions in equatorial positions and two Ag atoms at axial positions set up a trigonal bipyramid. These units are linked by the phosphine ligands into endless helical chains that run along the c axis. The crystal used for the data collection was a racemic twin.

Related literature

For related structures, see: Reddy et al. (1994 , 1995 ); Hu (2000 ).

Experimental

Crystal data

[Ag₂(NO₃)₂(C₂₈H₃₀N₂P₂)]
M_r = 796.24
Orthorhombic, P n a 2₁
a = 16.332 (1) Å
b = 20.6486 (13) Å
c = 9.0164 (5) Å
V = 3040.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.44 mm⁻¹
T = 173 K
0.22 × 0.08 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: analytical (SADABS; Bruker, 1999 ) T_min = 0.788, T_max = 0.907
13103 measured reflections
8801 independent reflections
6217 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.161
S = 1.01
8801 reflections
380 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.73 e Å⁻³
Absolute structure: Flack (1983 ), 3898 Friedel pairs
Flack parameter: 0.53 (4)

Data collection: SMART-NT (Bruker, 1998 ); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810019094/fk2018sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810019094/fk2018Isup2.hkl

checkCIF report

Comment top

The centre of a polymeric α-helix produced by the title compound is filled by nitrate counter ions. Three oxygen atoms from three different nitrate ions occupy the equatorial positions of a trigonal bipyramid and two silver atoms are situated at the axial positions. This complex arrangement connects each silver atom of one complex to a silver atom in a neighbouring complex. The resulting α-helices (Figure 2) are packed parallel to each other and run down the c-axis of the crystal.

Polymerisation in silver nitrate complexes analogous to the title compound is commonly encountered. For example, the case of (NO₃)Ag(dppe)Ag(NO₃) that forms long chains with P—Ag—P units as the connecting entity (Hu, 2000). These long chains are also periodically connected by short chains of Ag—O—Ag bonds, giving rise to sheets of connected complexes. The Ag—P bond distances of 2.334 (2) Å and 2.349 (2) Å in the title compound are considerably shorter than those of (NO₃)Ag(dppe)Ag(NO₃) (2.41 Å and 2.42 Å). The trigonal bipyramidal structure of the title compound consists of four long Ag—O bonds in the range of 2.5 Å and two short Ag—O bonds in the range of 2.3 Å. Two longer bonds are to the same NO₃^-, while two sets of a short and long bond are connected to the other two nitrates, respectively. This compares to Ag—O bond lengths between 2.68 Å and 2.17 Å in (NO₃)Ag(dppe)Ag(NO₃). The title compound exhibits Ag—O—Ag angles in the range of 93° to 99° and O—Ag—O angles in the range of 66° to 75°.

Related literature top

For related structures, see: Reddy et al. (1994, 1995); Hu (2000).

Experimental top

Silver nitrate (100 mg, 0.59 mmol) was suspended in THF or dissolved in the minimum amount of acetonitrile. To the stirred suspension were added 0.5 equivalents of bis(diphenylphosphino)-1,2-diethylhydrazine (132 mg, 0.29 mmol) in dichloromethane (DCM) (5 ml). The suspension turned light brown. The solvent was removed in vacuo to afford the product as a solid (65% yield).

The title compound crystallised from a mixture of acetonitrile, ethylacetate and hexane after being left at -20 °C for two weeks.

Structure description top

For related structures, see: Reddy et al. (1994, 1995); Hu (2000).

Computing details top

Data collection: SMART-NT (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. : Molecular structure of I drawn with displacement ellipsoids at the 50 % probability level. Hydrogen atoms have been omitted for clarity.
	Fig. 2. : Mercury representation of I showing the polymeric helix. Hydrogen atoms have been omitted for clarity.

Poly[[µ-1,2-bis(diphenylphosphanyl)-1,2-diethylhydrazine]-µ₄-nitrato- µ₂-disilver(I)] top

Crystal data top

[Ag₂(NO₃)₂(C₂₈H₃₀N₂P₂)]	F(000) = 1592
M_r = 796.24	D_x = 1.739 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3919 reflections
a = 16.332 (1) Å	θ = 2.3–26.5°
b = 20.6486 (13) Å	µ = 1.44 mm⁻¹
c = 9.0164 (5) Å	T = 173 K
V = 3040.6 (3) Å³	Needle, colourless
Z = 4	0.22 × 0.08 × 0.07 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	8801 independent reflections
Radiation source: fine-focus sealed tube	6217 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
phi and ω scans	θ_max = 30.5°, θ_min = 1.6°
Absorption correction: analytical (SADABS; Bruker, 1999)	h = −20→23
T_min = 0.788, T_max = 0.907	k = −10→29
13103 measured reflections	l = −12→12

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.161	w = 1/[σ²(F_o²) + (0.0891P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.006
8801 reflections	Δρ_max = 0.58 e Å⁻³
380 parameters	Δρ_min = −0.73 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 3898 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.53 (4)

Crystal data top

[Ag₂(NO₃)₂(C₂₈H₃₀N₂P₂)]	V = 3040.6 (3) Å³
M_r = 796.24	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 16.332 (1) Å	µ = 1.44 mm⁻¹
b = 20.6486 (13) Å	T = 173 K
c = 9.0164 (5) Å	0.22 × 0.08 × 0.07 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	8801 independent reflections
Absorption correction: analytical (SADABS; Bruker, 1999)	6217 reflections with I > 2σ(I)
T_min = 0.788, T_max = 0.907	R_int = 0.051
13103 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.161	Δρ_max = 0.58 e Å⁻³
S = 1.01	Δρ_min = −0.73 e Å⁻³
8801 reflections	Absolute structure: Flack (1983), 3898 Friedel pairs
380 parameters	Absolute structure parameter: 0.53 (4)
1 restraint

Special details top

Experimental. Intensity data were collected on a Bruker SMART1K CCD area detector diffractometer with graphite monochromated Mo Kα radiation (40 kV, 40 mA). The collection method involved ω-scans of width 0.3°. Data reduction was carried out using the program SAINT+ (Bruker, 1999) and face indexed absorption corrections were made using the program SAINT+ SADABS.

¹H NMR: (d-DMSO, 300 MHz) δ_H7.79 (bs, Arom), 7.64 (bs, Arom), 7.54 (bs, Arom), 3.19 (m, CH₂CH₃), 0.57 (t, ³J(¹H-¹H) = 6.6 Hz, CH₂CH₃).¹³C NMR: (CDCl₃, 100.6 MHz) δ_C 135.8 (s,Arom), 134.0 (Arom), 131.2 (m, Arom), 128.2 (s, Arom), ethyl signals could not be observed. ³¹P NMR: (d-DMSO, 121 MHz) δ_P 77.14 (d, ¹J (^107/109Ag-³¹P)= 782.9 Hz). MS: 733 (5 %, M - NO₃), 563 (7 %, Ligand + Ag). EA: Calc: (Ag₂P₂N₄O₆C₂₈H₃₀) C 42.24% H 3.80% N 7.04%. Found: C 41.48% H 3.95% N 6.77%. MP: 182 – 183 °C.

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. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
C1	0.1939 (6)	0.2253 (5)	0.8345 (9)	0.044 (2)
H1A	0.1595	0.2635	0.8325	0.053*
H1B	0.2486	0.2394	0.8613	0.053*
C2	0.1976 (7)	0.1994 (4)	0.6833 (12)	0.057 (3)
H2A	0.2186	0.2320	0.6175	0.086*
H2B	0.1437	0.1870	0.6520	0.086*
H2C	0.2330	0.1623	0.6813	0.086*
C3	0.2810 (5)	0.1667 (3)	1.1170 (9)	0.0296 (16)
H3A	0.3098	0.2001	1.0621	0.036*
H3B	0.3203	0.1334	1.1430	0.036*
C4	0.2457 (6)	0.1971 (4)	1.2633 (9)	0.042 (2)
H4A	0.2897	0.2147	1.3213	0.063*
H4B	0.2180	0.1642	1.3195	0.063*
H4C	0.2078	0.2309	1.2387	0.063*
C11	0.0019 (4)	0.1970 (3)	0.8645 (8)	0.0258 (14)
C12	−0.0291 (4)	0.1410 (3)	0.7955 (10)	0.0324 (16)
H12	−0.0198	0.1007	0.8387	0.039*
C13	−0.0742 (5)	0.1446 (4)	0.6624 (11)	0.043 (2)
H13	−0.0899	0.1069	0.6140	0.051*
C14	−0.0947 (7)	0.2036 (5)	0.6040 (12)	0.055 (3)
H14	−0.1265	0.2066	0.5187	0.066*
C15	−0.0663 (8)	0.2597 (4)	0.6771 (14)	0.073 (4)
H15	−0.0794	0.3003	0.6394	0.087*
C16	−0.0200 (6)	0.2550 (4)	0.8018 (11)	0.050 (2)
H16	−0.0022	0.2930	0.8469	0.061*
C21	0.0544 (4)	0.2647 (3)	1.1204 (7)	0.0232 (14)
C22	0.1097 (5)	0.3142 (4)	1.1123 (9)	0.0343 (17)
H22	0.1579	0.3089	1.0586	0.041*
C23	0.0939 (5)	0.3735 (4)	1.1854 (11)	0.0387 (18)
H23	0.1300	0.4080	1.1749	0.046*
C24	0.0265 (5)	0.3800 (4)	1.2701 (9)	0.0364 (18)
H24	0.0169	0.4190	1.3188	0.044*
C25	−0.0285 (5)	0.3300 (4)	1.2860 (10)	0.0372 (17)
H25	−0.0741	0.3345	1.3469	0.045*
C26	−0.0146 (4)	0.2725 (4)	1.2090 (9)	0.0339 (18)
H26	−0.0521	0.2387	1.2170	0.041*
C31	0.2553 (4)	0.0102 (3)	1.0819 (8)	0.0197 (13)
C32	0.2246 (5)	0.0190 (4)	1.2244 (9)	0.0330 (17)
H32	0.1968	0.0569	1.2486	0.040*
C33	0.2358 (5)	−0.0291 (4)	1.3306 (8)	0.0369 (18)
H33	0.2176	−0.0223	1.4271	0.044*
C34	0.2745 (5)	−0.0883 (4)	1.2934 (11)	0.0424 (19)
H34	0.2799	−0.1212	1.3632	0.051*
C35	0.3038 (5)	−0.0959 (4)	1.1521 (11)	0.040 (2)
H35	0.3317	−0.1337	1.1282	0.048*
C36	0.2933 (5)	−0.0499 (4)	1.0457 (9)	0.0317 (16)
H36	0.3109	−0.0577	0.9493	0.038*
C41	0.3281 (4)	0.0657 (3)	0.8277 (7)	0.0225 (14)
C42	0.3247 (4)	0.0570 (3)	0.6732 (9)	0.0300 (14)
H42	0.2741	0.0544	0.6261	0.036*
C43	0.3958 (5)	0.0522 (4)	0.5907 (9)	0.0341 (17)
H43	0.3932	0.0445	0.4891	0.041*
C44	0.4710 (5)	0.0589 (4)	0.6604 (12)	0.0411 (19)
H44	0.5186	0.0585	0.6037	0.049*
C45	0.4768 (4)	0.0661 (3)	0.8130 (10)	0.0331 (16)
H45	0.5276	0.0679	0.8595	0.040*
C46	0.4062 (5)	0.0705 (3)	0.8933 (9)	0.0301 (15)
H46	0.4098	0.0770	0.9951	0.036*
N1	0.1635 (4)	0.1824 (3)	0.9553 (6)	0.0232 (12)
N2	0.2181 (3)	0.1384 (3)	1.0214 (6)	0.0222 (11)
N3	0.0603 (4)	0.0379 (3)	1.4801 (6)	0.0229 (12)
N4	0.1688 (4)	−0.1152 (3)	0.6966 (9)	0.0337 (15)
O1	0.0241 (3)	0.0220 (2)	1.3584 (5)	0.0275 (11)
O2	0.0429 (3)	0.0039 (3)	1.5915 (5)	0.0341 (12)
O3	0.1085 (4)	0.0816 (3)	1.4847 (6)	0.0413 (15)
O4	0.1100 (3)	−0.1018 (3)	0.7843 (6)	0.0352 (12)
O5	0.2198 (3)	−0.0715 (3)	0.6727 (8)	0.0440 (13)
O6	0.1766 (4)	−0.1688 (3)	0.6396 (12)	0.077 (3)
P1	0.06706 (11)	0.18681 (8)	1.02502 (19)	0.0209 (3)
P2	0.23174 (10)	0.06614 (8)	0.93328 (19)	0.0200 (3)
Ag1	0.03083 (3)	0.09899 (3)	1.17410 (7)	0.03480 (15)
Ag2	0.12155 (3)	0.02110 (3)	0.80136 (7)	0.03238 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.044 (5)	0.057 (5)	0.032 (5)	0.005 (4)	0.013 (4)	0.017 (4)
C2	0.101 (8)	0.033 (4)	0.039 (5)	−0.004 (5)	0.012 (6)	−0.003 (4)
C3	0.030 (4)	0.019 (3)	0.040 (4)	0.002 (3)	−0.007 (3)	−0.009 (3)
C4	0.048 (5)	0.047 (5)	0.031 (4)	0.004 (4)	−0.006 (3)	−0.009 (4)
C11	0.029 (3)	0.019 (3)	0.029 (3)	0.006 (3)	−0.001 (3)	−0.001 (3)
C12	0.044 (4)	0.018 (3)	0.035 (4)	0.005 (3)	−0.013 (4)	0.000 (3)
C13	0.040 (4)	0.052 (5)	0.037 (4)	−0.004 (4)	−0.015 (4)	−0.014 (4)
C14	0.078 (7)	0.044 (5)	0.042 (5)	−0.004 (5)	−0.032 (5)	0.007 (4)
C15	0.127 (10)	0.026 (4)	0.065 (6)	0.006 (5)	−0.053 (8)	0.016 (5)
C16	0.078 (6)	0.027 (4)	0.047 (5)	−0.002 (4)	−0.024 (6)	0.007 (4)
C21	0.023 (3)	0.028 (3)	0.019 (3)	0.007 (3)	0.001 (2)	0.003 (3)
C22	0.038 (4)	0.032 (4)	0.033 (4)	−0.009 (3)	0.012 (3)	−0.001 (3)
C23	0.045 (4)	0.026 (4)	0.045 (5)	−0.010 (3)	0.005 (4)	−0.008 (4)
C24	0.037 (4)	0.031 (4)	0.041 (5)	0.003 (3)	0.000 (3)	−0.012 (3)
C25	0.037 (4)	0.032 (4)	0.042 (5)	0.004 (3)	0.007 (4)	−0.005 (4)
C26	0.027 (4)	0.034 (4)	0.041 (5)	−0.006 (3)	0.009 (3)	−0.002 (3)
C31	0.021 (3)	0.009 (3)	0.030 (3)	0.002 (2)	−0.003 (3)	−0.002 (2)
C32	0.035 (4)	0.031 (4)	0.032 (4)	0.007 (3)	0.009 (3)	−0.004 (3)
C33	0.049 (5)	0.038 (4)	0.024 (4)	0.003 (3)	−0.004 (3)	0.009 (3)
C34	0.047 (5)	0.042 (4)	0.038 (4)	0.012 (4)	−0.014 (4)	0.004 (4)
C35	0.046 (4)	0.020 (3)	0.054 (6)	0.009 (3)	−0.005 (4)	0.008 (3)
C36	0.040 (4)	0.024 (3)	0.031 (4)	0.007 (3)	0.002 (3)	0.003 (3)
C41	0.023 (3)	0.016 (3)	0.029 (4)	0.001 (2)	0.000 (3)	0.001 (2)
C42	0.037 (4)	0.022 (3)	0.031 (3)	−0.005 (3)	0.004 (4)	−0.005 (3)
C43	0.041 (4)	0.034 (4)	0.027 (4)	−0.005 (3)	0.010 (3)	0.004 (3)
C44	0.038 (4)	0.033 (4)	0.052 (5)	−0.002 (3)	0.019 (4)	−0.005 (4)
C45	0.025 (3)	0.025 (3)	0.049 (5)	−0.001 (3)	0.000 (4)	0.000 (4)
C46	0.030 (4)	0.027 (3)	0.034 (4)	−0.003 (3)	0.001 (3)	−0.002 (3)
N1	0.027 (3)	0.016 (3)	0.026 (3)	−0.004 (2)	0.007 (2)	0.007 (2)
N2	0.025 (3)	0.017 (3)	0.025 (3)	0.004 (2)	−0.004 (2)	−0.002 (2)
N3	0.026 (3)	0.022 (3)	0.021 (3)	0.003 (2)	0.001 (2)	0.004 (2)
N4	0.027 (3)	0.024 (3)	0.050 (4)	−0.001 (2)	−0.001 (3)	0.002 (3)
O1	0.035 (3)	0.032 (3)	0.015 (2)	−0.002 (2)	−0.0068 (19)	−0.002 (2)
O2	0.041 (3)	0.044 (3)	0.017 (2)	−0.014 (3)	−0.005 (2)	0.011 (2)
O3	0.050 (4)	0.042 (3)	0.032 (3)	−0.030 (3)	0.002 (2)	−0.003 (2)
O4	0.028 (3)	0.040 (3)	0.038 (3)	0.000 (2)	−0.004 (2)	0.001 (3)
O5	0.042 (3)	0.037 (3)	0.053 (3)	−0.007 (2)	0.008 (3)	0.016 (3)
O6	0.052 (4)	0.039 (4)	0.140 (9)	0.000 (3)	0.005 (5)	−0.036 (5)
P1	0.0242 (8)	0.0176 (7)	0.0208 (8)	0.0003 (6)	0.0012 (7)	0.0031 (6)
P2	0.0233 (8)	0.0177 (7)	0.0189 (7)	0.0008 (6)	−0.0012 (7)	−0.0023 (6)
Ag1	0.0332 (3)	0.0326 (3)	0.0385 (3)	−0.0076 (2)	0.0000 (3)	0.0181 (3)
Ag2	0.0332 (3)	0.0337 (3)	0.0302 (3)	−0.0068 (2)	−0.0103 (3)	−0.0043 (3)

Geometric parameters (Å, º) top

C1—C2	1.466 (13)	C32—H32	0.9300
C1—N1	1.489 (9)	C33—C34	1.416 (11)
C1—H1A	0.9700	C33—H33	0.9300
C1—H1B	0.9700	C34—C35	1.370 (14)
C2—H2A	0.9600	C34—H34	0.9300
C2—H2B	0.9600	C35—C36	1.361 (11)
C2—H2C	0.9600	C35—H35	0.9300
C3—N2	1.464 (9)	C36—H36	0.9300
C3—C4	1.570 (11)	C41—C42	1.406 (10)
C3—H3A	0.9700	C41—C46	1.409 (10)
C3—H3B	0.9700	C41—P2	1.839 (7)
C4—H4A	0.9600	C42—C43	1.383 (10)
C4—H4B	0.9600	C42—H42	0.9300
C4—H4C	0.9600	C43—C44	1.387 (12)
C11—C16	1.373 (11)	C43—H43	0.9300
C11—C12	1.408 (10)	C44—C45	1.387 (13)
C11—P1	1.808 (8)	C44—H44	0.9300
C12—C13	1.410 (12)	C45—C46	1.364 (11)
C12—H12	0.9300	C45—H45	0.9300
C13—C14	1.367 (13)	C46—H46	0.9300
C13—H13	0.9300	N1—N2	1.406 (8)
C14—C15	1.412 (14)	N1—P1	1.698 (6)
C14—H14	0.9300	N2—P2	1.704 (6)
C15—C16	1.359 (14)	N3—O3	1.197 (7)
C15—H15	0.9300	N3—O2	1.258 (7)
C16—H16	0.9300	N3—O1	1.288 (8)
C21—C22	1.365 (10)	N4—O6	1.227 (9)
C21—C26	1.391 (10)	N4—O5	1.247 (8)
C21—P1	1.836 (7)	N4—O4	1.275 (9)
C22—C23	1.414 (11)	O1—Ag1	2.302 (5)
C22—H22	0.9300	O1—Ag2ⁱ	2.592 (5)
C23—C24	1.347 (12)	O2—Ag2ⁱⁱ	2.314 (5)
C23—H23	0.9300	O2—Ag1ⁱ	2.553 (5)
C24—C25	1.376 (11)	O4—Ag1ⁱⁱⁱ	2.506 (5)
C24—H24	0.9300	O4—Ag2	2.549 (5)
C25—C26	1.394 (11)	P1—Ag1	2.3335 (18)
C25—H25	0.9300	P2—Ag2	2.3492 (18)
C26—H26	0.9300	Ag1—O4ⁱ	2.506 (5)
C31—C32	1.392 (10)	Ag1—O2ⁱⁱⁱ	2.553 (5)
C31—C36	1.426 (9)	Ag2—O2^iv	2.314 (5)
C31—P2	1.810 (7)	Ag2—O1ⁱⁱⁱ	2.592 (5)
C32—C33	1.392 (10)

C2—C1—N1	118.5 (8)	C33—C34—H34	120.8
C2—C1—H1A	107.7	C36—C35—C34	122.1 (8)
N1—C1—H1A	107.7	C36—C35—H35	118.9
C2—C1—H1B	107.7	C34—C35—H35	118.9
N1—C1—H1B	107.7	C35—C36—C31	120.1 (8)
H1A—C1—H1B	107.1	C35—C36—H36	119.9
C1—C2—H2A	109.5	C31—C36—H36	119.9
C1—C2—H2B	109.5	C42—C41—C46	117.4 (6)
H2A—C2—H2B	109.5	C42—C41—P2	118.6 (5)
C1—C2—H2C	109.5	C46—C41—P2	123.9 (5)
H2A—C2—H2C	109.5	C43—C42—C41	120.6 (7)
H2B—C2—H2C	109.5	C43—C42—H42	119.7
N2—C3—C4	113.4 (6)	C41—C42—H42	119.7
N2—C3—H3A	108.9	C42—C43—C44	119.5 (7)
C4—C3—H3A	108.9	C42—C43—H43	120.2
N2—C3—H3B	108.9	C44—C43—H43	120.2
C4—C3—H3B	108.9	C43—C44—C45	121.4 (7)
H3A—C3—H3B	107.7	C43—C44—H44	119.3
C3—C4—H4A	109.5	C45—C44—H44	119.3
C3—C4—H4B	109.5	C46—C45—C44	118.4 (7)
H4A—C4—H4B	109.5	C46—C45—H45	120.8
C3—C4—H4C	109.5	C44—C45—H45	120.8
H4A—C4—H4C	109.5	C45—C46—C41	122.5 (7)
H4B—C4—H4C	109.5	C45—C46—H46	118.7
C16—C11—C12	116.2 (7)	C41—C46—H46	118.7
C16—C11—P1	125.8 (6)	N2—N1—C1	118.9 (6)
C12—C11—P1	118.1 (5)	N2—N1—P1	117.7 (4)
C11—C12—C13	121.3 (7)	C1—N1—P1	123.3 (5)
C11—C12—H12	119.3	N1—N2—C3	115.9 (5)
C13—C12—H12	119.3	N1—N2—P2	116.8 (4)
C14—C13—C12	120.2 (8)	C3—N2—P2	122.2 (4)
C14—C13—H13	119.9	O3—N3—O2	122.8 (6)
C12—C13—H13	119.9	O3—N3—O1	121.5 (6)
C13—C14—C15	118.1 (8)	O2—N3—O1	115.7 (6)
C13—C14—H14	121.0	O6—N4—O5	120.8 (7)
C15—C14—H14	121.0	O6—N4—O4	122.3 (7)
C16—C15—C14	120.7 (8)	O5—N4—O4	116.9 (6)
C16—C15—H15	119.6	N3—O1—Ag1	114.6 (4)
C14—C15—H15	119.6	N3—O1—Ag2ⁱ	132.6 (4)
C15—C16—C11	123.2 (8)	Ag1—O1—Ag2ⁱ	97.89 (17)
C15—C16—H16	118.4	N3—O2—Ag2ⁱⁱ	116.2 (4)
C11—C16—H16	118.4	N3—O2—Ag1ⁱ	143.5 (4)
C22—C21—C26	118.8 (7)	Ag2ⁱⁱ—O2—Ag1ⁱ	98.69 (18)
C22—C21—P1	123.8 (5)	N4—O4—Ag1ⁱⁱⁱ	116.8 (5)
C26—C21—P1	117.4 (6)	N4—O4—Ag2	101.4 (4)
C21—C22—C23	120.1 (7)	Ag1ⁱⁱⁱ—O4—Ag2	93.95 (17)
C21—C22—H22	120.0	N1—P1—C11	104.8 (3)
C23—C22—H22	120.0	N1—P1—C21	108.9 (3)
C24—C23—C22	120.1 (7)	C11—P1—C21	102.0 (3)
C24—C23—H23	120.0	N1—P1—Ag1	114.0 (2)
C22—C23—H23	120.0	C11—P1—Ag1	113.7 (2)
C23—C24—C25	121.1 (7)	C21—P1—Ag1	112.5 (2)
C23—C24—H24	119.4	N2—P2—C31	103.9 (3)
C25—C24—H24	119.4	N2—P2—C41	111.0 (3)
C24—C25—C26	118.8 (7)	C31—P2—C41	101.4 (3)
C24—C25—H25	120.6	N2—P2—Ag2	118.8 (2)
C26—C25—H25	120.6	C31—P2—Ag2	106.6 (2)
C21—C26—C25	121.0 (7)	C41—P2—Ag2	113.0 (2)
C21—C26—H26	119.5	O1—Ag1—P1	164.66 (13)
C25—C26—H26	119.5	O1—Ag1—O4ⁱ	71.71 (19)
C32—C31—C36	118.8 (7)	P1—Ag1—O4ⁱ	116.31 (14)
C32—C31—P2	121.6 (5)	O1—Ag1—O2ⁱⁱⁱ	67.27 (17)
C36—C31—P2	118.6 (5)	P1—Ag1—O2ⁱⁱⁱ	126.75 (13)
C31—C32—C33	119.7 (7)	O4ⁱ—Ag1—O2ⁱⁱⁱ	72.66 (17)
C31—C32—H32	120.2	O2^iv—Ag2—P2	154.16 (13)
C33—C32—H32	120.2	O2^iv—Ag2—O4	75.92 (19)
C32—C33—C34	120.8 (8)	P2—Ag2—O4	118.77 (12)
C32—C33—H33	119.6	O2^iv—Ag2—O1ⁱⁱⁱ	66.42 (17)
C34—C33—H33	119.6	P2—Ag2—O1ⁱⁱⁱ	137.62 (12)
C35—C34—C33	118.4 (8)	O4—Ag2—O1ⁱⁱⁱ	66.56 (16)
C35—C34—H34	120.8

C16—C11—C12—C13	5.3 (12)	C12—C11—P1—N1	90.4 (6)
P1—C11—C12—C13	−174.2 (7)	C16—C11—P1—C21	24.5 (9)
C11—C12—C13—C14	−5.7 (14)	C12—C11—P1—C21	−156.0 (6)
C12—C13—C14—C15	2.9 (17)	C16—C11—P1—Ag1	145.8 (8)
C13—C14—C15—C16	0 (2)	C12—C11—P1—Ag1	−34.7 (7)
C14—C15—C16—C11	0 (2)	C22—C21—P1—N1	10.2 (7)
C12—C11—C16—C15	−2.4 (16)	C26—C21—P1—N1	−167.9 (6)
P1—C11—C16—C15	177.0 (10)	C22—C21—P1—C11	−100.2 (7)
C26—C21—C22—C23	−4.0 (12)	C26—C21—P1—C11	81.7 (6)
P1—C21—C22—C23	177.9 (7)	C22—C21—P1—Ag1	137.6 (6)
C21—C22—C23—C24	3.8 (14)	C26—C21—P1—Ag1	−40.5 (6)
C22—C23—C24—C25	−0.8 (14)	N1—N2—P2—C31	−150.4 (5)
C23—C24—C25—C26	−1.8 (13)	C3—N2—P2—C31	56.0 (6)
C22—C21—C26—C25	1.3 (12)	N1—N2—P2—C41	101.4 (5)
P1—C21—C26—C25	179.6 (6)	C3—N2—P2—C41	−52.2 (7)
C24—C25—C26—C21	1.6 (13)	N1—N2—P2—Ag2	−32.2 (5)
C36—C31—C32—C33	3.8 (11)	C3—N2—P2—Ag2	174.2 (5)
P2—C31—C32—C33	172.1 (6)	C32—C31—P2—N2	29.7 (7)
C31—C32—C33—C34	−3.1 (12)	C36—C31—P2—N2	−162.0 (5)
C32—C33—C34—C35	2.7 (13)	C32—C31—P2—C41	144.9 (6)
C33—C34—C35—C36	−3.2 (13)	C36—C31—P2—C41	−46.8 (6)
C34—C35—C36—C31	4.0 (13)	C32—C31—P2—Ag2	−96.6 (6)
C32—C31—C36—C35	−4.2 (11)	C36—C31—P2—Ag2	71.7 (6)
P2—C31—C36—C35	−172.8 (6)	C42—C41—P2—N2	−118.9 (5)
C46—C41—C42—C43	1.3 (10)	C46—C41—P2—N2	64.1 (6)
P2—C41—C42—C43	−175.9 (5)	C42—C41—P2—C31	131.1 (5)
C41—C42—C43—C44	−2.9 (11)	C46—C41—P2—C31	−45.8 (6)
C42—C43—C44—C45	4.3 (12)	C42—C41—P2—Ag2	17.4 (6)
C43—C44—C45—C46	−4.0 (12)	C46—C41—P2—Ag2	−159.5 (5)
C44—C45—C46—C41	2.4 (11)	N3—O1—Ag1—P1	20.1 (9)
C42—C41—C46—C45	−1.0 (10)	Ag2ⁱ—O1—Ag1—P1	164.7 (4)
P2—C41—C46—C45	175.9 (6)	N3—O1—Ag1—O4ⁱ	−103.9 (5)
C2—C1—N1—N2	82.7 (10)	Ag2ⁱ—O1—Ag1—O4ⁱ	40.72 (17)
C2—C1—N1—P1	−101.0 (9)	N3—O1—Ag1—O2ⁱⁱⁱ	177.7 (5)
C1—N1—N2—C3	71.4 (8)	Ag2ⁱ—O1—Ag1—O2ⁱⁱⁱ	−37.63 (16)
P1—N1—N2—C3	−105.2 (6)	N1—P1—Ag1—O1	60.8 (6)
C1—N1—N2—P2	−83.9 (7)	C11—P1—Ag1—O1	−179.2 (6)
P1—N1—N2—P2	99.5 (5)	C21—P1—Ag1—O1	−63.9 (6)
C4—C3—N2—N1	68.1 (8)	N1—P1—Ag1—O4ⁱ	179.4 (3)
C4—C3—N2—P2	−138.0 (6)	C11—P1—Ag1—O4ⁱ	−60.6 (3)
O3—N3—O1—Ag1	−16.4 (8)	C21—P1—Ag1—O4ⁱ	54.7 (3)
O2—N3—O1—Ag1	165.2 (5)	N1—P1—Ag1—O2ⁱⁱⁱ	−93.2 (3)
O3—N3—O1—Ag2ⁱ	−145.2 (5)	C11—P1—Ag1—O2ⁱⁱⁱ	26.8 (3)
O2—N3—O1—Ag2ⁱ	36.3 (9)	C21—P1—Ag1—O2ⁱⁱⁱ	142.1 (3)
O3—N3—O2—Ag2ⁱⁱ	−7.7 (9)	N2—P2—Ag2—O2^iv	91.3 (4)
O1—N3—O2—Ag2ⁱⁱ	170.8 (4)	C31—P2—Ag2—O2^iv	−151.9 (4)
O3—N3—O2—Ag1ⁱ	−169.2 (6)	C41—P2—Ag2—O2^iv	−41.4 (4)
O1—N3—O2—Ag1ⁱ	9.2 (11)	N2—P2—Ag2—O4	−148.9 (3)
O6—N4—O4—Ag1ⁱⁱⁱ	−67.3 (9)	C31—P2—Ag2—O4	−32.1 (3)
O5—N4—O4—Ag1ⁱⁱⁱ	114.0 (6)	C41—P2—Ag2—O4	78.4 (3)
O6—N4—O4—Ag2	−167.7 (8)	N2—P2—Ag2—O1ⁱⁱⁱ	−63.0 (3)
O5—N4—O4—Ag2	13.6 (7)	C31—P2—Ag2—O1ⁱⁱⁱ	53.8 (3)
N2—N1—P1—C11	−141.4 (5)	C41—P2—Ag2—O1ⁱⁱⁱ	164.3 (3)
C1—N1—P1—C11	42.3 (7)	N4—O4—Ag2—O2^iv	85.6 (4)
N2—N1—P1—C21	110.1 (5)	Ag1ⁱⁱⁱ—O4—Ag2—O2^iv	−32.81 (18)
C1—N1—P1—C21	−66.2 (7)	N4—O4—Ag2—P2	−71.5 (4)
N2—N1—P1—Ag1	−16.4 (5)	Ag1ⁱⁱⁱ—O4—Ag2—P2	170.14 (9)
C1—N1—P1—Ag1	167.2 (6)	N4—O4—Ag2—O1ⁱⁱⁱ	155.6 (5)
C16—C11—P1—N1	−89.0 (8)	Ag1ⁱⁱⁱ—O4—Ag2—O1ⁱⁱⁱ	37.26 (16)

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

Experimental details

Crystal data
Chemical formula	[Ag₂(NO₃)₂(C₂₈H₃₀N₂P₂)]
M_r	796.24
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	173
a, b, c (Å)	16.332 (1), 20.6486 (13), 9.0164 (5)
V (Å³)	3040.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.44
Crystal size (mm)	0.22 × 0.08 × 0.07

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Analytical (SADABS; Bruker, 1999)
T_min, T_max	0.788, 0.907
No. of measured, independent and observed [I > 2σ(I)] reflections	13103, 8801, 6217
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.714

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.161, 1.01
No. of reflections	8801
No. of parameters	380
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.73
Absolute structure	Flack (1983), 3898 Friedel pairs
Absolute structure parameter	0.53 (4)

Computer programs: SMART-NT (Bruker, 1998), SAINT-Plus (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008), WinGX (Farrugia, 1999).

Acknowledgements

The authors would like to thank Project AuTEK (Mintek and Harmony) and the University of the Witwatersrand for financial support.

References

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