Poly[[(μ3-isonicotinato-κ3O:O:N)(triphenyl­phosphine-κP)silver(I)] ethanol solvate]

Sadeghi, O.; Amini, M.M.; Ng, S.W.

doi:10.1107/S1600536810004733

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page m285

doi:10.1107/S1600536810004733

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Poly[[(μ₃-isonicotinato-κ³O:O:N)(triphenylphosphine-κP)silver(I)] ethanol solvate]

Omid Sadeghi,^a Mostafa M. Amini ^a and Seik Weng Ng ^b ^*

^aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran, Iran, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 15 January 2010; accepted 6 February 2010; online 13 February 2010)

In the crystal structure of {[Ag(C₆H₄NO₂)(C₁₈H₁₅P)]·C₂H₆O}_n, the 4-pyridylcarboxylate ion binds to the phosphine-coordinated silver atoms through one of the two oxygen atoms of the carboxyl unit, and to a third phosphine-coordinate silver atom through the nitrogen atom of the aromatic ring, giving a distorted tetrahedral coordination at the metal atom. The μ₃-bridging mode leads to a layer motif; the disordered ethanol molecules are linked to the free carboxyl oxygen atom by O—H⋯O hydrogen bonds.

Related literature

For the crystal structure of polymeric 4-pyridylcarboxylatosilver, see: Yang et al. (2004 ). For the synthesis of the reactant used in the metathetical reaction, see: Ng & Othman (1995 , 1997 ).

Experimental

Crystal data

[Ag(C₆H₄NO₂)(C₁₈H₁₅P)]·C₂H₆O
M_r = 538.31
Monoclinic, P 2₁ /c
a = 15.8026 (10) Å
b = 13.2430 (9) Å
c = 12.5483 (8) Å
β = 111.1937 (9)°
V = 2448.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.92 mm⁻¹
T = 295 K
0.40 × 0.20 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.711, T_max = 0.956
22818 measured reflections
5615 independent reflections
4111 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.078
S = 1.06
5615 reflections
308 parameters
29 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.84 (5)	1.92 (5)	2.749 (4)	172 (6)

Data collection: APEX2 software (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ), PLATON (Spek, 200 ) and OLEX (Dolomanov et al., 2003 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810004733/dn2530sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810004733/dn2530Isup2.hkl

checkCIF report

Comment top

Silver carboxylates form adducts with triphenylphosphine; silver acetate itself furnishes silver acetate^.2triphenylphosphine hemihydrate (Ng & Othman, 1995; Ng & Othman, 1997). The carboxylate unit in this adduct can be exchanged for a pyridylcarboxylate unit reacting the compound with the pyridylcarboxylic acid as the silver pyridylcarboxylate cannot be readily synthesized by condensing silver oxide with the pyridylcarboxylic acid.

In the crystal structure of Ag(C₆H₄NO₂)(C₁₈H₁₅P)^.C₂H₆O (Scheme I, Fig. 1), the anion binds through to to phosphine-cordinated silver atoms through one of the two oxygen atoms of the carboxyl unit and to a third phosphine-coordinate silver atom through the nitrogen atom of the aromatic ring to render tetrahedral coordination at the metal atom. The µ₃-bridging model leads to a layer motif (Fig. 2); the disordered ethanol molecules bind to the free carboxyl oxygen atom by hydrogen bonds.

Related literature top

For the crystal structure of polymeric 4-pyridylcarboxylatosilver, see: Yang et al. (2004). For the synthesis of the reactant used in the metathetical reaction, see: Ng & Othman (1995, 1997).

Experimental top

The bis-adduct, silver acetate^.2triphenylphosphine hemihydrate, was first synthesized by reacting silver acetate (1 mmol, 0.17 g) and triphenylphosphine (2 mmol, 0.53 g) in ethanol (50 ml) (Ng & Othman, 1995; Ng & Othman, 1997). The adduct was isolated as colorless crystals. The adduct, (1 mmol, 0.69 g) was reacted with 4-pyridinecarboxylic acid (1 mmol, 0.13 g ) in ethanol (50 ml). Slow evaporation of solvent afford suitable crystals (m.p. 408-409 K). The crystals rapidly turned opaque when taken out of solution. A specimen was coated in glue for the diffraction measurements.

Computing details top

Data collection: APEX2 software (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), PLATON (Spek, 2009) and OLEX (Dolomanov et al., 2003)'; software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. ORTEP view showing the coordination mode of the silver with the atom labeling scheme. Ellipsoids are shown at the 30% probability level. Hydrogen atoms and the disordered solvate have been omitted for clarity. [Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, y-1/2, -z+3/2; (iii) -x+1, y+1/2, -z+3/2; (iv) x, 1/2-y, z-1/2].
	Fig. 2. OLEX (Dolomanov et al., 2003) representation of the layer structure.

Poly[[(µ₃-isonicotinato-κ³O:O:N)(triphenylphosphine-κP)silver(I)] ethanol solvate] top

Crystal data top

[Ag(C₆H₄NO₂)(C₁₈H₁₅P)]·C₂H₆O	F(000) = 1096
M_r = 538.31	D_x = 1.460 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6635 reflections
a = 15.8026 (10) Å	θ = 2.4–28.1°
b = 13.2430 (9) Å	µ = 0.92 mm⁻¹
c = 12.5483 (8) Å	T = 295 K
β = 111.1937 (9)°	Block coated in glue, colorless
V = 2448.4 (3) Å³	0.40 × 0.20 × 0.05 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	5615 independent reflections
Radiation source: fine-focus sealed tube	4111 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ω scans	θ_max = 27.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→20
T_min = 0.711, T_max = 0.956	k = −17→17
22818 measured reflections	l = −15→16

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.029P)² + 1.2212P] where P = (F_o² + 2F_c²)/3
5615 reflections	(Δ/σ)_max = 0.002
308 parameters	Δρ_max = 0.41 e Å⁻³
29 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

[Ag(C₆H₄NO₂)(C₁₈H₁₅P)]·C₂H₆O	V = 2448.4 (3) Å³
M_r = 538.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.8026 (10) Å	µ = 0.92 mm⁻¹
b = 13.2430 (9) Å	T = 295 K
c = 12.5483 (8) Å	0.40 × 0.20 × 0.05 mm
β = 111.1937 (9)°

Data collection top

Bruker SMART APEX diffractometer	5615 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4111 reflections with I > 2σ(I)
T_min = 0.711, T_max = 0.956	R_int = 0.039
22818 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	29 restraints
wR(F²) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.41 e Å⁻³
5615 reflections	Δρ_min = −0.31 e Å⁻³
308 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ag1	0.614660 (14)	0.443563 (16)	0.564182 (18)	0.03977 (8)
P1	0.73287 (5)	0.49413 (6)	0.50219 (6)	0.03698 (17)
O1	0.53235 (13)	0.57005 (15)	0.61834 (16)	0.0421 (5)
O2	0.63385 (16)	0.54142 (18)	0.79082 (19)	0.0636 (7)
O3	0.7823 (2)	0.4374 (3)	0.9329 (3)	0.1018 (11)
H3	0.738 (3)	0.473 (4)	0.895 (4)	0.16 (3)*
N1	0.44392 (15)	0.81511 (17)	0.8642 (2)	0.0396 (5)
C1	0.83757 (19)	0.4219 (2)	0.5607 (3)	0.0444 (7)
C2	0.9230 (2)	0.4634 (3)	0.5938 (3)	0.0674 (10)
H2	0.9296	0.5324	0.5854	0.081*
C3	0.9994 (2)	0.4033 (4)	0.6393 (4)	0.0864 (13)
H3A	1.0568	0.4322	0.6616	0.104*
C4	0.9907 (3)	0.3027 (4)	0.6516 (4)	0.0881 (14)
H4	1.0422	0.2629	0.6832	0.106*
C5	0.9073 (3)	0.2598 (3)	0.6181 (4)	0.0944 (15)
H5	0.9015	0.1904	0.6243	0.113*
C6	0.8307 (2)	0.3198 (3)	0.5748 (4)	0.0725 (11)
H6	0.7736	0.2904	0.5548	0.087*
C7	0.70310 (19)	0.4873 (2)	0.3475 (2)	0.0392 (6)
C8	0.6256 (2)	0.5381 (2)	0.2796 (3)	0.0491 (8)
H8	0.5923	0.5752	0.3137	0.059*
C9	0.5973 (2)	0.5339 (3)	0.1614 (3)	0.0621 (9)
H9	0.5457	0.5688	0.1165	0.075*
C10	0.6454 (3)	0.4787 (3)	0.1113 (3)	0.0681 (10)
H10	0.6262	0.4755	0.0320	0.082*
C11	0.7216 (3)	0.4281 (3)	0.1764 (3)	0.0686 (11)
H11	0.7538	0.3905	0.1413	0.082*
C12	0.7516 (2)	0.4323 (3)	0.2954 (3)	0.0550 (8)
H12	0.8040	0.3982	0.3394	0.066*
C13	0.76577 (18)	0.6258 (2)	0.5340 (2)	0.0401 (6)
C14	0.8048 (2)	0.6813 (3)	0.4702 (3)	0.0565 (8)
H14	0.8170	0.6506	0.4107	0.068*
C15	0.8260 (3)	0.7820 (3)	0.4944 (3)	0.0705 (10)
H15	0.8528	0.8183	0.4515	0.085*
C16	0.8079 (3)	0.8284 (3)	0.5804 (3)	0.0680 (10)
H16	0.8214	0.8965	0.5955	0.082*
C17	0.7698 (2)	0.7747 (3)	0.6445 (3)	0.0633 (10)
H17	0.7578	0.8065	0.7036	0.076*
C18	0.7487 (2)	0.6734 (3)	0.6226 (3)	0.0500 (8)
H18	0.7232	0.6374	0.6672	0.060*
C19	0.56739 (18)	0.5860 (2)	0.7242 (2)	0.0368 (6)
C20	0.52434 (17)	0.6678 (2)	0.7719 (2)	0.0329 (6)
C21	0.44917 (19)	0.7210 (2)	0.7046 (2)	0.0408 (7)
H21	0.4240	0.7083	0.6265	0.049*
C22	0.41135 (19)	0.7928 (2)	0.7527 (3)	0.0451 (7)
H22	0.3606	0.8277	0.7053	0.054*
C23	0.5173 (2)	0.7646 (2)	0.9290 (2)	0.0442 (7)
H23	0.5416	0.7792	1.0067	0.053*
C24	0.55900 (19)	0.6919 (2)	0.8871 (2)	0.0421 (7)
H24	0.6104	0.6590	0.9359	0.051*
C25	0.8216 (4)	0.4024 (7)	0.8541 (5)	0.075 (3)	0.596 (11)
H25A	0.7898	0.4300	0.7785	0.090*	0.596 (11)
H25B	0.8197	0.3293	0.8494	0.090*	0.596 (11)
C26	0.9193 (4)	0.4398 (7)	0.9016 (7)	0.166 (6)	0.596 (11)
H26A	0.9505	0.4179	0.8528	0.248*	0.596 (11)
H26B	0.9492	0.4129	0.9770	0.248*	0.596 (11)
H26C	0.9198	0.5122	0.9051	0.248*	0.596 (11)
C25'	0.8433 (5)	0.4584 (7)	0.8721 (8)	0.118 (6)	0.404 (11)
H25C	0.8087	0.4779	0.7939	0.142*	0.404 (11)
H25D	0.8839	0.5134	0.9089	0.142*	0.404 (11)
C26'	0.8952 (4)	0.3674 (7)	0.8736 (11)	0.172 (9)	0.404 (11)
H26D	0.9253	0.3456	0.9512	0.259*	0.404 (11)
H26E	0.9396	0.3814	0.8398	0.259*	0.404 (11)
H26F	0.8551	0.3152	0.8310	0.259*	0.404 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.04098 (12)	0.04309 (13)	0.04407 (13)	0.00077 (10)	0.02597 (10)	0.00367 (10)
P1	0.0358 (3)	0.0432 (4)	0.0369 (4)	−0.0001 (3)	0.0191 (3)	0.0016 (3)
O1	0.0466 (11)	0.0507 (13)	0.0322 (11)	0.0068 (9)	0.0181 (9)	−0.0047 (9)
O2	0.0622 (14)	0.0722 (16)	0.0456 (13)	0.0335 (12)	0.0066 (11)	−0.0037 (11)
O3	0.095 (2)	0.137 (3)	0.0668 (19)	0.046 (2)	0.0219 (18)	0.0116 (19)
N1	0.0423 (13)	0.0414 (14)	0.0388 (13)	−0.0001 (10)	0.0189 (11)	−0.0078 (11)
C1	0.0389 (15)	0.054 (2)	0.0441 (17)	0.0064 (13)	0.0191 (13)	0.0031 (14)
C2	0.0427 (18)	0.077 (3)	0.084 (3)	0.0021 (17)	0.0237 (18)	0.014 (2)
C3	0.0393 (19)	0.108 (4)	0.111 (4)	0.004 (2)	0.025 (2)	0.011 (3)
C4	0.052 (2)	0.099 (4)	0.106 (4)	0.027 (2)	0.019 (2)	0.011 (3)
C5	0.069 (3)	0.066 (3)	0.136 (4)	0.015 (2)	0.021 (3)	0.013 (3)
C6	0.0487 (19)	0.058 (2)	0.101 (3)	0.0035 (17)	0.016 (2)	0.006 (2)
C7	0.0427 (15)	0.0412 (16)	0.0409 (16)	−0.0083 (12)	0.0238 (13)	−0.0022 (13)
C8	0.0466 (16)	0.060 (2)	0.0435 (18)	−0.0016 (14)	0.0200 (14)	−0.0002 (15)
C9	0.061 (2)	0.075 (3)	0.046 (2)	−0.0075 (18)	0.0134 (17)	0.0058 (17)
C10	0.089 (3)	0.075 (3)	0.043 (2)	−0.022 (2)	0.027 (2)	−0.0057 (19)
C11	0.094 (3)	0.073 (3)	0.055 (2)	0.000 (2)	0.047 (2)	−0.0152 (19)
C12	0.060 (2)	0.059 (2)	0.055 (2)	0.0043 (16)	0.0310 (17)	−0.0039 (16)
C13	0.0395 (15)	0.0447 (17)	0.0369 (15)	−0.0006 (12)	0.0148 (12)	0.0000 (13)
C14	0.071 (2)	0.052 (2)	0.056 (2)	−0.0092 (17)	0.0343 (18)	−0.0025 (16)
C15	0.085 (3)	0.057 (2)	0.074 (3)	−0.018 (2)	0.034 (2)	0.001 (2)
C16	0.067 (2)	0.051 (2)	0.072 (3)	−0.0088 (18)	0.008 (2)	−0.0078 (19)
C17	0.062 (2)	0.070 (2)	0.050 (2)	0.0034 (18)	0.0113 (17)	−0.0216 (18)
C18	0.0452 (17)	0.061 (2)	0.0399 (17)	0.0009 (15)	0.0113 (14)	−0.0038 (15)
C19	0.0396 (15)	0.0380 (15)	0.0366 (16)	0.0031 (12)	0.0182 (13)	−0.0003 (12)
C20	0.0352 (13)	0.0352 (14)	0.0310 (14)	0.0009 (11)	0.0152 (11)	−0.0012 (11)
C21	0.0433 (15)	0.0465 (17)	0.0308 (15)	0.0056 (13)	0.0113 (12)	−0.0043 (12)
C22	0.0417 (15)	0.0503 (18)	0.0394 (17)	0.0118 (13)	0.0101 (13)	−0.0030 (14)
C23	0.0508 (17)	0.0498 (18)	0.0311 (15)	−0.0003 (14)	0.0137 (13)	−0.0085 (13)
C24	0.0417 (15)	0.0491 (18)	0.0329 (15)	0.0093 (13)	0.0103 (12)	−0.0016 (13)
C25	0.067 (4)	0.092 (6)	0.068 (4)	0.020 (4)	0.025 (3)	−0.011 (4)
C26	0.146 (8)	0.201 (10)	0.167 (9)	−0.028 (7)	0.078 (7)	−0.039 (7)
C25'	0.121 (10)	0.111 (9)	0.106 (9)	0.028 (7)	0.020 (7)	−0.031 (7)
C26'	0.187 (13)	0.184 (13)	0.151 (11)	0.003 (9)	0.068 (9)	−0.019 (9)

Geometric parameters (Å, º) top

Ag1—P1	2.3651 (7)	C11—H11	0.9300
Ag1—O1	2.3662 (18)	C12—H12	0.9300
Ag1—O1ⁱ	2.6131 (19)	C13—C14	1.386 (4)
Ag1—N1ⁱⁱ	2.271 (2)	C13—C18	1.387 (4)
P1—C1	1.820 (3)	C14—C15	1.381 (5)
P1—C13	1.822 (3)	C14—H14	0.9300
P1—C7	1.827 (3)	C15—C16	1.359 (5)
O1—C19	1.259 (3)	C15—H15	0.9300
O2—C19	1.231 (3)	C16—C17	1.366 (5)
O3—C25	1.423 (4)	C16—H16	0.9300
O3—C25'	1.457 (5)	C17—C18	1.386 (5)
O3—H3	0.84 (5)	C17—H17	0.9300
N1—C23	1.331 (4)	C18—H18	0.9300
N1—C22	1.338 (3)	C19—C20	1.512 (4)
N1—Ag1ⁱⁱⁱ	2.271 (2)	C20—C21	1.377 (4)
C1—C6	1.373 (5)	C20—C24	1.385 (4)
C1—C2	1.375 (4)	C21—C22	1.374 (4)
C2—C3	1.384 (5)	C21—H21	0.9300
C2—H2	0.9300	C22—H22	0.9300
C3—C4	1.354 (6)	C23—C24	1.374 (4)
C3—H3A	0.9300	C23—H23	0.9300
C4—C5	1.356 (6)	C24—H24	0.9300
C4—H4	0.9300	C25—C26	1.523 (5)
C5—C6	1.383 (5)	C25—H25A	0.9700
C5—H5	0.9300	C25—H25B	0.9700
C6—H6	0.9300	C26—H26A	0.9600
C7—C12	1.381 (4)	C26—H26B	0.9600
C7—C8	1.387 (4)	C26—H26C	0.9600
C8—C9	1.387 (5)	C25'—C26'	1.4538
C8—H8	0.9300	C25'—H25C	0.9700
C9—C10	1.361 (5)	C25'—H25D	0.9700
C9—H9	0.9300	C26'—H26D	0.9600
C10—C11	1.362 (5)	C26'—H26E	0.9600
C10—H10	0.9300	C26'—H26F	0.9600
C11—C12	1.394 (5)

N1ⁱⁱ—Ag1—P1	145.63 (6)	C14—C13—C18	118.6 (3)
N1ⁱⁱ—Ag1—O1	94.11 (8)	C14—C13—P1	122.2 (2)
P1—Ag1—O1	118.40 (5)	C18—C13—P1	119.2 (2)
N1ⁱⁱ—Ag1—O1ⁱ	86.25 (7)	C15—C14—C13	120.6 (3)
P1—Ag1—O1ⁱ	106.79 (5)	C15—C14—H14	119.7
O1—Ag1—O1ⁱ	83.90 (6)	C13—C14—H14	119.7
C1—P1—C13	105.57 (14)	C16—C15—C14	120.5 (4)
C1—P1—C7	104.47 (13)	C16—C15—H15	119.8
C13—P1—C7	102.95 (13)	C14—C15—H15	119.8
C1—P1—Ag1	115.44 (10)	C15—C16—C17	119.7 (4)
C13—P1—Ag1	113.30 (9)	C15—C16—H16	120.1
C7—P1—Ag1	113.88 (9)	C17—C16—H16	120.1
C19—O1—Ag1	110.15 (16)	C16—C17—C18	120.9 (3)
C25—O3—H3	106 (4)	C16—C17—H17	119.6
C25'—O3—H3	100 (4)	C18—C17—H17	119.6
C23—N1—C22	116.7 (2)	C17—C18—C13	119.8 (3)
C23—N1—Ag1ⁱⁱⁱ	121.66 (18)	C17—C18—H18	120.1
C22—N1—Ag1ⁱⁱⁱ	121.41 (19)	C13—C18—H18	120.1
C6—C1—C2	117.9 (3)	O2—C19—O1	125.3 (3)
C6—C1—P1	117.8 (2)	O2—C19—C20	118.1 (2)
C2—C1—P1	124.2 (3)	O1—C19—C20	116.7 (2)
C1—C2—C3	120.6 (4)	C21—C20—C24	116.8 (2)
C1—C2—H2	119.7	C21—C20—C19	122.3 (2)
C3—C2—H2	119.7	C24—C20—C19	120.9 (2)
C4—C3—C2	120.2 (4)	C22—C21—C20	120.0 (3)
C4—C3—H3A	119.9	C22—C21—H21	120.0
C2—C3—H3A	119.9	C20—C21—H21	120.0
C3—C4—C5	120.3 (4)	N1—C22—C21	123.2 (3)
C3—C4—H4	119.9	N1—C22—H22	118.4
C5—C4—H4	119.9	C21—C22—H22	118.4
C4—C5—C6	119.7 (4)	N1—C23—C24	123.4 (3)
C4—C5—H5	120.2	N1—C23—H23	118.3
C6—C5—H5	120.2	C24—C23—H23	118.3
C1—C6—C5	121.2 (4)	C23—C24—C20	119.8 (3)
C1—C6—H6	119.4	C23—C24—H24	120.1
C5—C6—H6	119.4	C20—C24—H24	120.1
C12—C7—C8	118.9 (3)	O3—C25—C26	104.9 (5)
C12—C7—P1	123.7 (2)	O3—C25—H25A	110.8
C8—C7—P1	117.4 (2)	C26—C25—H25A	110.8
C7—C8—C9	120.6 (3)	O3—C25—H25B	110.8
C7—C8—H8	119.7	C26—C25—H25B	110.8
C9—C8—H8	119.7	H25A—C25—H25B	108.8
C10—C9—C8	119.8 (4)	C26'—C25'—O3	108.2 (7)
C10—C9—H9	120.1	C26'—C25'—H25C	110.1
C8—C9—H9	120.1	O3—C25'—H25C	110.1
C9—C10—C11	120.4 (3)	C26'—C25'—H25D	110.1
C9—C10—H10	119.8	O3—C25'—H25D	110.1
C11—C10—H10	119.8	H25C—C25'—H25D	108.4
C10—C11—C12	120.6 (3)	C25'—C26'—H26D	109.5
C10—C11—H11	119.7	C25'—C26'—H26E	109.5
C12—C11—H11	119.7	H26D—C26'—H26E	109.5
C7—C12—C11	119.7 (3)	C25'—C26'—H26F	109.5
C7—C12—H12	120.2	H26D—C26'—H26F	109.5
C11—C12—H12	120.2	H26E—C26'—H26F	109.5

N1ⁱⁱ—Ag1—P1—C1	−23.79 (16)	C9—C10—C11—C12	−0.2 (6)
O1—Ag1—P1—C1	135.40 (12)	C8—C7—C12—C11	−0.6 (5)
O1ⁱ—Ag1—P1—C1	−132.48 (12)	P1—C7—C12—C11	177.4 (3)
N1ⁱⁱ—Ag1—P1—C13	−145.70 (14)	C10—C11—C12—C7	0.7 (6)
O1—Ag1—P1—C13	13.50 (11)	C1—P1—C13—C14	78.6 (3)
O1ⁱ—Ag1—P1—C13	105.62 (11)	C7—P1—C13—C14	−30.7 (3)
N1ⁱⁱ—Ag1—P1—C7	97.08 (15)	Ag1—P1—C13—C14	−154.1 (2)
O1—Ag1—P1—C7	−103.72 (12)	C1—P1—C13—C18	−103.5 (2)
O1ⁱ—Ag1—P1—C7	−11.60 (12)	C7—P1—C13—C18	147.2 (2)
N1ⁱⁱ—Ag1—O1—C19	75.80 (19)	Ag1—P1—C13—C18	23.8 (3)
P1—Ag1—O1—C19	−92.60 (18)	C18—C13—C14—C15	−0.2 (5)
O1ⁱ—Ag1—O1—C19	161.6 (2)	P1—C13—C14—C15	177.7 (3)
C13—P1—C1—C6	163.9 (3)	C13—C14—C15—C16	−0.7 (6)
C7—P1—C1—C6	−87.9 (3)	C14—C15—C16—C17	1.0 (6)
Ag1—P1—C1—C6	37.9 (3)	C15—C16—C17—C18	−0.4 (6)
C13—P1—C1—C2	−14.8 (3)	C16—C17—C18—C13	−0.5 (5)
C7—P1—C1—C2	93.4 (3)	C14—C13—C18—C17	0.8 (4)
Ag1—P1—C1—C2	−140.8 (3)	P1—C13—C18—C17	−177.2 (2)
C6—C1—C2—C3	0.2 (6)	Ag1—O1—C19—O2	−1.2 (4)
P1—C1—C2—C3	178.9 (3)	Ag1—O1—C19—C20	177.99 (18)
C1—C2—C3—C4	0.2 (7)	O2—C19—C20—C21	−179.2 (3)
C2—C3—C4—C5	0.8 (8)	O1—C19—C20—C21	1.6 (4)
C3—C4—C5—C6	−2.2 (8)	O2—C19—C20—C24	0.3 (4)
C2—C1—C6—C5	−1.6 (6)	O1—C19—C20—C24	−179.0 (3)
P1—C1—C6—C5	179.6 (4)	C24—C20—C21—C22	−1.0 (4)
C4—C5—C6—C1	2.6 (7)	C19—C20—C21—C22	178.4 (3)
C1—P1—C7—C12	3.2 (3)	C23—N1—C22—C21	0.8 (4)
C13—P1—C7—C12	113.3 (3)	Ag1ⁱⁱⁱ—N1—C22—C21	174.9 (2)
Ag1—P1—C7—C12	−123.6 (2)	C20—C21—C22—N1	0.0 (5)
C1—P1—C7—C8	−178.8 (2)	C22—N1—C23—C24	−0.7 (4)
C13—P1—C7—C8	−68.7 (2)	Ag1ⁱⁱⁱ—N1—C23—C24	−174.7 (2)
Ag1—P1—C7—C8	54.3 (2)	N1—C23—C24—C20	−0.4 (5)
C12—C7—C8—C9	−0.1 (5)	C21—C20—C24—C23	1.2 (4)
P1—C7—C8—C9	−178.2 (2)	C19—C20—C24—C23	−178.3 (3)
C7—C8—C9—C10	0.7 (5)	C25'—O3—C25—C26	38.5 (4)
C8—C9—C10—C11	−0.5 (6)	C25—O3—C25'—C26'	−41.6 (7)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.84 (5)	1.92 (5)	2.749 (4)	172 (6)

Experimental details

Crystal data
Chemical formula	[Ag(C₆H₄NO₂)(C₁₈H₁₅P)]·C₂H₆O
M_r	538.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	15.8026 (10), 13.2430 (9), 12.5483 (8)
β (°)	111.1937 (9)
V (Å³)	2448.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.92
Crystal size (mm)	0.40 × 0.20 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.711, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	22818, 5615, 4111
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.078, 1.06
No. of reflections	5615
No. of parameters	308
No. of restraints	29
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.31

Computer programs: APEX2 software (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), PLATON (Spek, 2009) and OLEX (Dolomanov et al., 2003)', publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.84 (5)	1.92 (5)	2.749 (4)	172 (6)

Acknowledgements

We thank Shahid Beheshti University and the University of Malaya for supporting this study.

References

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