[Bis[μ-bis­(diphenyl­phosphino)methane-1:2κ2P:P′]-bis­(nitrito-κ2O,O′)]disilver(I) acetonitrile disolvate

Yang, X.; Huang, X.; Qiu, Q.-M.; Jin, Q.-H.; Zhang, C.-L.

doi:10.1107/S1600536812041931

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page m1367

doi:10.1107/S1600536812041931

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[Bis[μ-bis(diphenylphosphino)methane-1:2κ²P:P′]-bis(nitrito-κ²O,O′)]disilver(I) acetonitrile disolvate

Xue Yang,^a Xu Huang,^a Qi-Ming Qiu,^a Qiong-Hua Jin ^a ^* and Cun-Lin Zhang ^b

^aDepartment of Chemistry, Capital Normal University, Beijing 100048, People's Republic of China, and ^bKey Laboratory of Terahertz Optoelectronics, Ministry of Education, Department of Physics, Capital Normal University, Beijing 100048, People's Republic of China
^*Correspondence e-mail: jinqh204@163.com

(Received 1 September 2012; accepted 7 October 2012; online 13 October 2012)

The title complex, [Ag₂(NO₂)₂(C₂₅H₂₂P₂)₂]·2CH₃CN, is a centrosymmetric dimer in which two bis(diphenylphosphino)methane ligands bridge two Ag⁺ ions, forming an eight-membered ring with a short Ag⋯Ag separation of 3.1809 (5) Å. The distorted P₂O₂ coordination of the cation is completed by two O-donors from a symmetric bidentate chelate NO₂⁻ anion [Ag—O = 2.550 (3) and 2.567 (3) Å].

Related literature

The coordination chemistry of silver(I) complexes has been extensively studied, see: Bowmaker et al. (1993 ); Cui, Hu et al. (2010 ); Cui, Jin et al. (2010 ); Jin, Hu et al. (2010 ); Jin, Song et al. (2010 ); Meijboom et al. (2009 ). For related structures, see: Effendy et al. (2004 ); Jin et al. (2008 ); Ma et al. (2009 ); Song et al. (2010 ).

Experimental

Crystal data

[Ag₂(NO₂)₂(C₂₅H₂₂P₂)₂]·2C₂H₃N
M_r = 1158.60
Monoclinic, P 2₁ /n
a = 12.1390 (11) Å
b = 11.1247 (9) Å
c = 20.0350 (18) Å
β = 95.543 (1)°
V = 2692.9 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.89 mm⁻¹
T = 298 K
0.40 × 0.35 × 0.33 mm

Data collection

Bruker SMART CCD area detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.717, T_max = 0.757
13205 measured reflections
4752 independent reflections
3845 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.090
S = 1.07
4752 reflections
308 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 1.01 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Data collection: SMART (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812041931/zs2232sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812041931/zs2232Isup2.hkl

checkCIF report

Comment top

The coordination chemistry of silver(I) complexes has been extensively studied because of their luminescence properties and potential applications in catalysis, photography, antimicrobial activities and electrochemical processes (Bowmaker et al., 1993; Cui, Hu et al., 2010; Cui, Jin et al., 2010; Jin, Hu et al., 2010; Jin, Song et al., 2010; Meijboom et al., 2009). Recently, some silver(I) complexes containing phosphine ligands and coordinated anions have been reported (Jin et al., 2008; Song et al., 2010). Continuing these efforts, we synthesized a new complex using AgNO₂, bis(diphenylphosphino)methane (dppm) and 1,2-bis(4-pyridyl)ethane, the title compound [Ag₂(dppm)₂(NO₂)₂] . 2(CH₃CN), and the structure is reported here.

In the title compound two silver atoms are bridged by two dppm ligands, giving a centrosymmetric dimer (Fig. 1) having a Ag···Ag distance of 3.1809 (5) Å, which is longer than that found in the analogous complex [Ag₂L₂](SO₃CF₃)₂ (L = 4'-phenylterpyridine) [2.9452 (4) Å] (Ma et al., 2009). Each of the two NO₂^- anions chelates an Ag atom with Ag—O bond distances of 2.550 (3) and 2.567 (3) Å, so each Ag atom is tetracoordinated. These values compare with 2.694 (4) and 2.559 (5) Å in a similar crystal [AgNO₂(dppm)]₂, which was synthesized in methanol (Effendy et al., 2004). In the title complex, the P2—Ag1—P1 angle is 144.82 (3)°, the O1—Ag1—O2 angle is 47.98 (10)°, while the P—Ag1—O angles are in the range of 85.18 (7)–129.41 (7)°, indicating a very distorted tetrahedral stereochemistry about the two silver(I) atoms. The Ag1—P1 and Ag1—P2 bond lengths are 2.4747 (8) and 2.4395 (9) Å, which are both longer than the Ag—P bond found in [Ag(NCS)(C₂₅H₂₂P₂)]_n (Song et al., 2010), which is analogous to the title compound, synthesized using a similar reaction in the presence of 1,10-phenanthroline.

Related literature top

The coordination chemistry of silver(I) complexes has been extensively studied because of their luminescence properties and antimicrobial activity and potential applications in catalysis, photography and electrochemical processes, see: Bowmaker et al. (1993); Cui, Hu et al. (2010); Cui, Jin et al. (2010); Jin, Hu et al. (2010); Jin, Song et al. (2010); Meijboom et al. (2009). For related structures, see: Effendy et al. (2004); Jin et al. (2008); Ma et al. (2009); Song et al. (2010).

Experimental top

The title complex was synthesized using the following procedure. Bis(diphenylphosphino)methane (dppm, 0.0769 g, 0.2 mmol) was added to a stirred solution of AgNO₂ (0.0308 g, 0.2 mmol) and 1,2-bis(4-pyridyl)ethane (0.0368 g, 0.2 mmol) in a mixture of CH₃CN (5 ml) and H₂O (5 ml). Stirring was continued for 6 h at room temperature, after which the white precipitate was filtered off. Subsequent slow evaporation of the colorless filtrate at ambient temperature resulted in the formation of colorless crystals of the title complex. Crystals suitable for single-crystal X-ray diffraction were selected directly from the sample as prepared.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular [Ag₂(C₂₅H₂₂P₂)₂(NO₂)₂].2(CH₃CN), showing the atom-numbering scheme, with displacement ellipsoids drawn at the 30% probability level. For symmetry code (i): -x+1, -y+1, -z+1.

[Bis[µ-bis(diphenylphosphino)methane-1:2κ²P:P']- bis(nitrito-κ²O,O')]disilver(I) acetonitrile disolvate top

Crystal data top

[Ag₂(NO₂)₂(C₂₅H₂₂P₂)₂]·2C₂H₃N	F(000) = 1176
M_r = 1158.60	D_x = 1.429 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6670 reflections
a = 12.1390 (11) Å	θ = 2.5–28.2°
b = 11.1247 (9) Å	µ = 0.89 mm⁻¹
c = 20.0350 (18) Å	T = 298 K
β = 95.543 (1)°	Block, colourless
V = 2692.9 (4) Å³	0.40 × 0.35 × 0.33 mm
Z = 2

Data collection top

Bruker SMART CCD area detector diffractometer	4752 independent reflections
Radiation source: fine-focus sealed tube	3845 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −14→13
T_min = 0.717, T_max = 0.757	k = −13→13
13205 measured reflections	l = −23→18

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.037P)² + 2.4337P] where P = (F_o² + 2F_c²)/3
4752 reflections	(Δ/σ)_max = 0.002
308 parameters	Δρ_max = 1.01 e Å⁻³
3 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

[Ag₂(NO₂)₂(C₂₅H₂₂P₂)₂]·2C₂H₃N	V = 2692.9 (4) Å³
M_r = 1158.60	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.1390 (11) Å	µ = 0.89 mm⁻¹
b = 11.1247 (9) Å	T = 298 K
c = 20.0350 (18) Å	0.40 × 0.35 × 0.33 mm
β = 95.543 (1)°

Data collection top

Bruker SMART CCD area detector diffractometer	4752 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	3845 reflections with I > 2σ(I)
T_min = 0.717, T_max = 0.757	R_int = 0.035
13205 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	3 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 1.07	Δρ_max = 1.01 e Å⁻³
4752 reflections	Δρ_min = −0.46 e Å⁻³
308 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
Ag1	0.43541 (2)	0.61579 (2)	0.521730 (12)	0.03586 (10)
P1	0.55178 (7)	0.70130 (8)	0.43866 (4)	0.0324 (2)
P2	0.43562 (7)	0.53526 (8)	0.63500 (4)	0.0327 (2)
N1	0.2195 (3)	0.6845 (4)	0.44450 (19)	0.0626 (10)
N2	0.9358 (7)	0.8704 (8)	0.6794 (5)	0.154 (3)
O1	0.2546 (3)	0.7319 (3)	0.49890 (16)	0.0729 (9)
O2	0.2823 (2)	0.6093 (3)	0.42403 (16)	0.0627 (7)
C1	0.5182 (3)	0.6221 (3)	0.35872 (17)	0.0369 (8)
H1A	0.5540	0.6623	0.3236	0.044*
H1B	0.4389	0.6247	0.3467	0.044*
C2	0.5182 (3)	0.8565 (3)	0.41655 (17)	0.0373 (8)
C3	0.4172 (3)	0.8834 (3)	0.3812 (2)	0.0498 (10)
H3	0.3691	0.8215	0.3669	0.060*
C4	0.3871 (4)	1.0011 (4)	0.3668 (2)	0.0649 (12)
H4	0.3198	1.0177	0.3424	0.078*
C5	0.4561 (5)	1.0931 (4)	0.3883 (2)	0.0682 (14)
H5	0.4352	1.1722	0.3791	0.082*
C6	0.5555 (4)	1.0693 (4)	0.4234 (2)	0.0619 (12)
H6	0.6021	1.1322	0.4381	0.074*
C7	0.5875 (3)	0.9515 (3)	0.43718 (19)	0.0485 (9)
H7	0.6561	0.9359	0.4605	0.058*
C8	0.7019 (3)	0.6971 (3)	0.45118 (18)	0.0412 (8)
C9	0.7677 (3)	0.7389 (4)	0.4033 (2)	0.0649 (12)
H9	0.7354	0.7722	0.3635	0.078*
C10	0.8810 (4)	0.7309 (6)	0.4150 (3)	0.0925 (18)
H10	0.9250	0.7602	0.3831	0.111*
C11	0.9295 (4)	0.6809 (6)	0.4720 (4)	0.110 (2)
H11	1.0063	0.6755	0.4788	0.131*
C12	0.8664 (5)	0.6385 (6)	0.5193 (4)	0.108 (2)
H12	0.8997	0.6032	0.5582	0.129*
C13	0.7513 (4)	0.6482 (4)	0.5093 (2)	0.0674 (13)
H13	0.7081	0.6214	0.5421	0.081*
C14	0.5351 (3)	0.6152 (3)	0.69330 (16)	0.0374 (8)
C15	0.5009 (4)	0.7003 (4)	0.73770 (18)	0.0523 (10)
H15	0.4260	0.7099	0.7425	0.063*
C16	0.5793 (4)	0.7712 (4)	0.7751 (2)	0.0650 (12)
H16	0.5563	0.8270	0.8054	0.078*
C17	0.6881 (4)	0.7596 (4)	0.7676 (2)	0.0667 (13)
H17	0.7393	0.8089	0.7919	0.080*
C18	0.7238 (4)	0.6755 (4)	0.7245 (2)	0.0620 (11)
H18	0.7990	0.6668	0.7202	0.074*
C19	0.6475 (3)	0.6034 (3)	0.6872 (2)	0.0479 (9)
H19	0.6719	0.5467	0.6579	0.057*
C20	0.3075 (3)	0.5396 (3)	0.67562 (18)	0.0447 (9)
C21	0.2194 (4)	0.6045 (4)	0.6469 (2)	0.0674 (13)
H21	0.2235	0.6428	0.6060	0.081*
C22	0.1227 (4)	0.6127 (6)	0.6800 (3)	0.101 (2)
H22	0.0635	0.6591	0.6618	0.121*
C23	0.1159 (5)	0.5525 (7)	0.7387 (3)	0.097 (2)
H23	0.0509	0.5561	0.7596	0.117*
C24	0.2022 (5)	0.4879 (6)	0.7670 (3)	0.0867 (17)
H24	0.1966	0.4478	0.8072	0.104*
C25	0.2989 (4)	0.4813 (4)	0.7361 (2)	0.0630 (12)
H25	0.3586	0.4376	0.7559	0.076*
C26	0.9176 (7)	0.9290 (8)	0.6327 (6)	0.124 (3)
C27	0.8934 (8)	1.0016 (10)	0.5727 (5)	0.182 (4)
H27A	0.8406	0.9604	0.5420	0.273*
H27B	0.9603	1.0147	0.5517	0.273*
H27C	0.8633	1.0775	0.5846	0.273*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.04039 (16)	0.03674 (17)	0.03093 (15)	0.00023 (11)	0.00592 (11)	0.00355 (11)
P1	0.0365 (5)	0.0316 (5)	0.0294 (4)	−0.0030 (4)	0.0052 (4)	0.0017 (4)
P2	0.0383 (5)	0.0328 (5)	0.0274 (4)	−0.0006 (4)	0.0060 (4)	0.0002 (4)
N1	0.045 (2)	0.081 (3)	0.060 (2)	0.0081 (19)	−0.0008 (17)	0.015 (2)
N2	0.131 (6)	0.147 (7)	0.176 (8)	0.016 (5)	−0.029 (6)	−0.015 (6)
O1	0.0686 (18)	0.088 (2)	0.0610 (19)	0.0234 (16)	0.0020 (16)	−0.0021 (15)
O2	0.0537 (17)	0.069 (2)	0.0640 (18)	0.0051 (15)	−0.0012 (12)	−0.0018 (13)
C1	0.0462 (19)	0.0323 (18)	0.0326 (18)	−0.0010 (15)	0.0057 (15)	0.0028 (14)
C2	0.051 (2)	0.0306 (18)	0.0323 (18)	−0.0031 (15)	0.0126 (16)	0.0013 (14)
C3	0.058 (2)	0.035 (2)	0.056 (2)	−0.0002 (18)	0.0018 (19)	0.0038 (17)
C4	0.080 (3)	0.050 (3)	0.065 (3)	0.014 (2)	0.008 (2)	0.015 (2)
C5	0.111 (4)	0.039 (2)	0.060 (3)	0.009 (3)	0.034 (3)	0.013 (2)
C6	0.096 (4)	0.033 (2)	0.061 (3)	−0.015 (2)	0.031 (3)	−0.009 (2)
C7	0.061 (2)	0.044 (2)	0.043 (2)	−0.0107 (19)	0.0157 (18)	−0.0063 (17)
C8	0.0367 (18)	0.040 (2)	0.047 (2)	−0.0064 (15)	0.0066 (16)	−0.0043 (17)
C9	0.051 (2)	0.087 (3)	0.059 (3)	−0.016 (2)	0.020 (2)	−0.007 (2)
C10	0.057 (3)	0.115 (5)	0.112 (5)	−0.020 (3)	0.039 (3)	−0.021 (4)
C11	0.034 (3)	0.118 (5)	0.176 (7)	−0.006 (3)	0.009 (4)	−0.010 (5)
C12	0.053 (3)	0.124 (5)	0.139 (6)	0.000 (3)	−0.029 (4)	0.038 (4)
C13	0.049 (2)	0.075 (3)	0.076 (3)	−0.004 (2)	−0.005 (2)	0.021 (3)
C14	0.050 (2)	0.0329 (18)	0.0287 (17)	−0.0038 (15)	0.0016 (15)	0.0020 (14)
C15	0.067 (3)	0.052 (2)	0.040 (2)	−0.004 (2)	0.0121 (19)	−0.0085 (18)
C16	0.096 (4)	0.055 (3)	0.043 (2)	−0.011 (3)	0.006 (2)	−0.017 (2)
C17	0.082 (3)	0.058 (3)	0.055 (3)	−0.017 (2)	−0.021 (2)	−0.006 (2)
C18	0.054 (2)	0.065 (3)	0.064 (3)	−0.006 (2)	−0.011 (2)	0.000 (2)
C19	0.048 (2)	0.046 (2)	0.048 (2)	0.0000 (17)	−0.0022 (18)	−0.0030 (18)
C20	0.048 (2)	0.050 (2)	0.039 (2)	−0.0062 (18)	0.0155 (17)	−0.0082 (17)
C21	0.051 (2)	0.095 (4)	0.057 (3)	0.011 (2)	0.014 (2)	0.001 (3)
C22	0.050 (3)	0.152 (6)	0.104 (5)	0.020 (3)	0.023 (3)	−0.006 (4)
C23	0.073 (4)	0.136 (6)	0.090 (4)	−0.018 (4)	0.049 (3)	−0.028 (4)
C24	0.091 (4)	0.106 (4)	0.071 (3)	−0.021 (4)	0.049 (3)	−0.008 (3)
C25	0.070 (3)	0.072 (3)	0.051 (3)	−0.008 (2)	0.024 (2)	0.006 (2)
C26	0.106 (6)	0.106 (6)	0.158 (9)	0.002 (5)	−0.001 (6)	−0.026 (6)
C27	0.182 (9)	0.176 (10)	0.190 (10)	−0.011 (8)	0.035 (8)	0.040 (9)

Geometric parameters (Å, º) top

Ag1—P2	2.4396 (9)	C10—H10	0.9300
Ag1—P1	2.4747 (9)	C11—C12	1.360 (9)
Ag1—O1	2.550 (3)	C11—H11	0.9300
Ag1—O2	2.567 (3)	C12—C13	1.396 (7)
Ag1—Ag1ⁱ	3.1809 (5)	C12—H12	0.9300
P1—C8	1.816 (3)	C13—H13	0.9300
P1—C2	1.819 (3)	C14—C19	1.388 (5)
P1—C1	1.839 (3)	C14—C15	1.390 (5)
P2—C20	1.824 (4)	C15—C16	1.397 (6)
P2—C14	1.827 (3)	C15—H15	0.9300
P2—C1ⁱ	1.839 (3)	C16—C17	1.350 (6)
N1—O2	1.229 (4)	C16—H16	0.9300
N1—O1	1.248 (5)	C17—C18	1.372 (6)
N2—C26	1.144 (11)	C17—H17	0.9300
C1—P2ⁱ	1.839 (3)	C18—C19	1.387 (6)
C1—H1A	0.9700	C18—H18	0.9300
C1—H1B	0.9700	C19—H19	0.9300
C2—C3	1.388 (5)	C20—C21	1.371 (6)
C2—C7	1.389 (5)	C20—C25	1.387 (5)
C3—C4	1.382 (5)	C21—C22	1.405 (6)
C3—H3	0.9300	C21—H21	0.9300
C4—C5	1.365 (7)	C22—C23	1.364 (9)
C4—H4	0.9300	C22—H22	0.9300
C5—C6	1.363 (7)	C23—C24	1.349 (8)
C5—H5	0.9300	C23—H23	0.9300
C6—C7	1.387 (6)	C24—C25	1.381 (6)
C6—H6	0.9300	C24—H24	0.9300
C7—H7	0.9300	C25—H25	0.9300
C8—C13	1.369 (6)	C26—C27	1.455 (12)
C8—C9	1.387 (5)	C27—H27A	0.9600
C9—C10	1.376 (7)	C27—H27B	0.9600
C9—H9	0.9300	C27—H27C	0.9600
C10—C11	1.353 (9)

P2—Ag1—P1	144.82 (3)	C11—C10—C9	121.2 (5)
P2—Ag1—O1	106.05 (8)	C11—C10—H10	119.4
P1—Ag1—O1	102.83 (8)	C9—C10—H10	119.4
P2—Ag1—O2	129.40 (7)	C10—C11—C12	120.1 (5)
P1—Ag1—O2	85.19 (7)	C10—C11—H11	119.9
O1—Ag1—O2	47.95 (10)	C12—C11—H11	119.9
P2—Ag1—Ag1ⁱ	90.06 (2)	C11—C12—C13	119.8 (6)
P1—Ag1—Ag1ⁱ	78.39 (2)	C11—C12—H12	120.1
O1—Ag1—Ag1ⁱ	143.11 (8)	C13—C12—H12	120.1
O2—Ag1—Ag1ⁱ	96.21 (7)	C8—C13—C12	120.2 (5)
C8—P1—C2	104.87 (17)	C8—C13—H13	119.9
C8—P1—C1	104.07 (17)	C12—C13—H13	119.9
C2—P1—C1	102.52 (15)	C19—C14—C15	118.5 (3)
C8—P1—Ag1	121.84 (12)	C19—C14—P2	119.5 (3)
C2—P1—Ag1	113.54 (11)	C15—C14—P2	121.4 (3)
C1—P1—Ag1	107.99 (11)	C14—C15—C16	119.8 (4)
C20—P2—C14	103.94 (16)	C14—C15—H15	120.1
C20—P2—C1ⁱ	105.18 (17)	C16—C15—H15	120.1
C14—P2—C1ⁱ	103.96 (16)	C17—C16—C15	120.7 (4)
C20—P2—Ag1	118.75 (13)	C17—C16—H16	119.7
C14—P2—Ag1	110.93 (11)	C15—C16—H16	119.7
C1ⁱ—P2—Ag1	112.72 (11)	C16—C17—C18	120.4 (4)
O2—N1—O1	114.1 (3)	C16—C17—H17	119.8
N1—O1—Ag1	99.1 (2)	C18—C17—H17	119.8
N1—O2—Ag1	98.8 (2)	C17—C18—C19	119.9 (4)
P1—C1—P2ⁱ	110.85 (18)	C17—C18—H18	120.1
P1—C1—H1A	109.5	C19—C18—H18	120.1
P2ⁱ—C1—H1A	109.5	C18—C19—C14	120.6 (4)
P1—C1—H1B	109.5	C18—C19—H19	119.7
P2ⁱ—C1—H1B	109.5	C14—C19—H19	119.7
H1A—C1—H1B	108.1	C21—C20—C25	119.4 (4)
C3—C2—C7	117.9 (3)	C21—C20—P2	119.4 (3)
C3—C2—P1	119.7 (3)	C25—C20—P2	121.1 (3)
C7—C2—P1	122.3 (3)	C20—C21—C22	119.3 (5)
C4—C3—C2	120.9 (4)	C20—C21—H21	120.3
C4—C3—H3	119.6	C22—C21—H21	120.3
C2—C3—H3	119.6	C23—C22—C21	119.9 (6)
C5—C4—C3	120.2 (4)	C23—C22—H22	120.1
C5—C4—H4	119.9	C21—C22—H22	120.1
C3—C4—H4	119.9	C24—C23—C22	121.0 (5)
C6—C5—C4	120.2 (4)	C24—C23—H23	119.5
C6—C5—H5	119.9	C22—C23—H23	119.5
C4—C5—H5	119.9	C23—C24—C25	120.0 (5)
C5—C6—C7	120.2 (4)	C23—C24—H24	120.0
C5—C6—H6	119.9	C25—C24—H24	120.0
C7—C6—H6	119.9	C24—C25—C20	120.4 (5)
C6—C7—C2	120.6 (4)	C24—C25—H25	119.8
C6—C7—H7	119.7	C20—C25—H25	119.8
C2—C7—H7	119.7	N2—C26—C27	178.9 (11)
C13—C8—C9	119.1 (4)	C26—C27—H27A	109.5
C13—C8—P1	118.6 (3)	C26—C27—H27B	109.5
C9—C8—P1	122.2 (3)	H27A—C27—H27B	109.5
C10—C9—C8	119.5 (5)	C26—C27—H27C	109.5
C10—C9—H9	120.2	H27A—C27—H27C	109.5
C8—C9—H9	120.2	H27B—C27—H27C	109.5

P2—Ag1—P1—C8	11.22 (16)	C4—C5—C6—C7	0.3 (7)
O1—Ag1—P1—C8	155.83 (16)	C5—C6—C7—C2	−1.1 (6)
O2—Ag1—P1—C8	−159.29 (16)	C3—C2—C7—C6	0.8 (5)
Ag1ⁱ—Ag1—P1—C8	−61.93 (14)	P1—C2—C7—C6	−175.4 (3)
P2—Ag1—P1—C2	−115.66 (13)	C2—P1—C8—C13	128.7 (3)
O1—Ag1—P1—C2	28.95 (15)	C1—P1—C8—C13	−124.0 (3)
O2—Ag1—P1—C2	73.83 (14)	Ag1—P1—C8—C13	−1.9 (4)
Ag1ⁱ—Ag1—P1—C2	171.19 (13)	C2—P1—C8—C9	−52.9 (4)
P2—Ag1—P1—C1	131.39 (12)	C1—P1—C8—C9	54.4 (4)
O1—Ag1—P1—C1	−84.01 (14)	Ag1—P1—C8—C9	176.5 (3)
O2—Ag1—P1—C1	−39.13 (13)	C13—C8—C9—C10	−0.1 (7)
Ag1ⁱ—Ag1—P1—C1	58.23 (12)	P1—C8—C9—C10	−178.5 (4)
P1—Ag1—P2—C20	156.55 (14)	C8—C9—C10—C11	1.1 (9)
O1—Ag1—P2—C20	12.54 (16)	C9—C10—C11—C12	−0.6 (11)
O2—Ag1—P2—C20	−35.73 (17)	C10—C11—C12—C13	−0.8 (11)
Ag1ⁱ—Ag1—P2—C20	−133.82 (14)	C9—C8—C13—C12	−1.3 (7)
P1—Ag1—P2—C14	36.27 (14)	P1—C8—C13—C12	177.1 (4)
O1—Ag1—P2—C14	−107.73 (15)	C11—C12—C13—C8	1.8 (9)
O2—Ag1—P2—C14	−156.00 (15)	C20—P2—C14—C19	163.7 (3)
Ag1ⁱ—Ag1—P2—C14	105.91 (12)	C1ⁱ—P2—C14—C19	53.8 (3)
P1—Ag1—P2—C1ⁱ	−79.84 (14)	Ag1—P2—C14—C19	−67.6 (3)
O1—Ag1—P2—C1ⁱ	136.15 (15)	C20—P2—C14—C15	−25.3 (3)
O2—Ag1—P2—C1ⁱ	87.89 (16)	C1ⁱ—P2—C14—C15	−135.1 (3)
Ag1ⁱ—Ag1—P2—C1ⁱ	−10.21 (13)	Ag1—P2—C14—C15	103.5 (3)
O2—N1—O1—Ag1	−2.0 (4)	C19—C14—C15—C16	−0.2 (5)
P2—Ag1—O1—N1	−127.9 (2)	P2—C14—C15—C16	−171.3 (3)
P1—Ag1—O1—N1	72.4 (3)	C14—C15—C16—C17	1.2 (6)
O2—Ag1—O1—N1	1.2 (2)	C15—C16—C17—C18	−1.8 (7)
Ag1ⁱ—Ag1—O1—N1	−15.2 (3)	C16—C17—C18—C19	1.3 (7)
O1—N1—O2—Ag1	2.0 (4)	C17—C18—C19—C14	−0.2 (6)
P2—Ag1—O2—N1	73.8 (3)	C15—C14—C19—C18	−0.3 (6)
P1—Ag1—O2—N1	−113.3 (2)	P2—C14—C19—C18	171.0 (3)
O1—Ag1—O2—N1	−1.2 (2)	C14—P2—C20—C21	113.3 (3)
Ag1ⁱ—Ag1—O2—N1	169.0 (2)	C1ⁱ—P2—C20—C21	−137.8 (3)
C8—P1—C1—P2ⁱ	62.7 (2)	Ag1—P2—C20—C21	−10.5 (4)
C2—P1—C1—P2ⁱ	171.77 (18)	C14—P2—C20—C25	−64.7 (4)
Ag1—P1—C1—P2ⁱ	−68.08 (18)	C1ⁱ—P2—C20—C25	44.2 (4)
C8—P1—C2—C3	157.2 (3)	Ag1—P2—C20—C25	171.5 (3)
C1—P1—C2—C3	48.7 (3)	C25—C20—C21—C22	1.2 (7)
Ag1—P1—C2—C3	−67.5 (3)	P2—C20—C21—C22	−176.8 (4)
C8—P1—C2—C7	−26.7 (3)	C20—C21—C22—C23	−2.5 (9)
C1—P1—C2—C7	−135.1 (3)	C21—C22—C23—C24	2.1 (10)
Ag1—P1—C2—C7	108.7 (3)	C22—C23—C24—C25	−0.5 (9)
C7—C2—C3—C4	0.3 (6)	C23—C24—C25—C20	−0.8 (8)
P1—C2—C3—C4	176.6 (3)	C21—C20—C25—C24	0.4 (7)
C2—C3—C4—C5	−1.1 (6)	P2—C20—C25—C24	178.4 (4)
C3—C4—C5—C6	0.8 (7)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Ag₂(NO₂)₂(C₂₅H₂₂P₂)₂]·2C₂H₃N
M_r	1158.60
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	12.1390 (11), 11.1247 (9), 20.0350 (18)
β (°)	95.543 (1)
V (Å³)	2692.9 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.89
Crystal size (mm)	0.40 × 0.35 × 0.33

Data collection
Diffractometer	Bruker SMART CCD area detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.717, 0.757
No. of measured, independent and observed [I > 2σ(I)] reflections	13205, 4752, 3845
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.090, 1.07
No. of reflections	4752
No. of parameters	308
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.01, −0.46

Computer programs: SMART (Bruker, 2007), SAINT-Plus (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 21171119), the National High Technology Research and Development Program 863 of China (2012AA063201), the Beijing Personnel Bureau, the National Keystone Basic Research Program (973 Program) under grant Nos. 2007CB310408 and 2006CB302901 and the Committee of Education of the Beijing Foundation of China (grant No. KM201210028020).

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