Bis(1,10-phenanthroline-5,6-dione-κ2N,N′)silver(I) tetra­fluoridoborate

Onuegbu, J.; Butcher, R.J.; Hosten, C.; Udeochu, U.C.; Bakare, O.

doi:10.1107/S160053680903222X

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Pages m1119-m1120

doi:10.1107/S160053680903222X

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Bis(1,10-phenanthroline-5,6-dione-κ²N,N′)silver(I) tetrafluoridoborate

Jonathan Onuegbu,^a Ray J. Butcher,^a ^* Charles Hosten,^a Uche Charles Udeochu ^a and Oladapo Bakare ^a

^aDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
^*Correspondence e-mail: rbutcher99@yahoo.com

(Received 12 August 2009; accepted 13 August 2009; online 22 August 2009)

In the structure of the title compound, [Ag(C₁₂H₆N₂O₂)₂]BF₄ or [AgL₂]BF₄ (L = phendione), the Ag and B atoms are located on twofold rotation axes. The dihedral angle between the two phendione ligands is 36.7 (2)°. The coordination about the Ag^I center is distorted tetrahedral (τ₄ = 0.546). The crystal structure is consolidated by weak C—H⋯O(phendione) and C—H⋯F(BF₄⁻) interactions. The BF₄⁻ counter-anion is strongly disordered and was modelled with two sets of idealized F atoms.

Related literature

For the different coordination properties of phendione, see: Calderazzo et al. (1999 , 2002 ); Calucci et al. (2006 ); Galet et al. (2005 ); Lei et al. (1996 ); Okamura et al. (2006 ). For examples with phendione ligands where N and O donors are used simultaneously, see: Fox et al. (1991 ); Shavaleev et al. (2003a ,b ); Ruiz et al. (1999 ); Paw & Eisenberg (1997 ). Similar structures containing Ag have also been reported by Onuegbu et al. (2007 ). For background to phendione chemistry, see: Udeochu et al. (2007 ); Onuegbu et al. (2007). For reference structural data, see: Allen (2002 ); Leschke et al. (2002 ); Paramonov et al. (2003 ); Pallenberg et al. (1997 ); Titze et al. (1997 ). Details of the τ₄ parameter were given by Yang et al. (2007 ).

Experimental

Crystal data

[Ag(C₁₂H₆N₂O₂)₂]BF₄
M_r = 615.06
Monoclinic, C 2/c
a = 13.2249 (6) Å
b = 12.0115 (17) Å
c = 14.4338 (7) Å
β = 108.481 (5)°
V = 2174.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.01 mm⁻¹
T = 200 K
0.44 × 0.37 × 0.28 mm

Data collection

Oxford Diffraction Gemini R diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction. (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.856, T_max = 1.000 (expected range = 0.646–0.755)
11815 measured reflections
3647 independent reflections
2306 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.134
S = 0.98
3647 reflections
204 parameters
32 restraints
H-atom parameters constrained
Δρ_max = 1.81 e Å⁻³
Δρ_min = −1.39 e Å⁻³

Table 1
Selected bond lengths (Å)

Ag—N1	2.356 (2)
Ag—N2	2.357 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O1ⁱ	0.95	2.51	3.347 (4)	147
C1—H1A⋯F1Aⁱⁱ	0.95	2.35	3.083 (6)	133
C2—H2A⋯F1B	0.95	2.17	2.803 (8)	123
C10—H10A⋯F2Aⁱⁱⁱ	0.95	2.24	2.859 (5)	122
C10—H10A⋯F2B^iv	0.95	2.28	3.065 (4)	140
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y-1, -z+{\script{1\over 2}}]$ ; (iv) x, y-1, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 $[Oxford Diffraction. (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction. (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); data reduction: CrysAlis RED; 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/S160053680903222X/wm2249sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680903222X/wm2249Isup2.hkl

checkCIF report

Comment top

Phendione (1,10-phenanthroline-5,6-dione) is an excellent ligand that incorporates two functional groups with different coordination properties (Calderazzo et al., 1999, 2002; Calucci et al., 2006; Galet et al., 2005; Lei et al., 1996; Okamura et al., 2006). This well known ligand possesses both the α-diimine and orthoquinone moieties. While phendione usually binds to metals through its imine N atoms, in some cases both the N and O donors are used simultaneously (Fox et al., 1991; Shavaleev et al., 2003a, b; Ruiz et al., 1999; Paw & Eisenberg, 1997). The crystal structures of two complexes of copper and phendione have been determined (Galet et al., 2005;). Similar structures containing Ag have also been reported (Onuegbu et al., 2007). In this paper, as part of our study of phendione chemistry (Udeochu et al., 2007; Onuegbu et al., 2007), we report the synthesis and characterization of the title compound, [AgL₂]⁺(BF₄)^-, (I).

The structure of (I), shown in Figure 1, is made up of an [Ag(L)₂]⁺ cation and a tetrafluoridoborate anion. The silver atom is coordinated to the two nitrogen atoms of both phendione ligands. Both the Ag atom of the cation and the B atom of the anion lie on a crystallographic twofold rotation axes. The C═O bond lengths in the phendione ligands (1.210 (4) and 1.206 (3) Å) are comparable to those values found in other such complexes (Allen, 2002; Onuegbu et al., 2007). The Ag—N bond lengths (2.356 (2) and 2.357 (2) Å) are similar to those found in related phenanthroline derivatives of silver (Leschke et al., 2002; Paramonov et al., 2003; Pallenberg et al., 1997; Titze et al., 1997).

In (I), the silver cation is in a distorted tetrahedral environment. This is best illustrated by the dihedral angle between the planes of the coordinated ligands which in this case the angle is 36.7 (2)°. This compares with values of 36.8 (2)° found in the analogous perchlorate analog and the values of 32.4° and 70.5° found for other structurally characterized Ag complexes containing the bis(1,10-phenanthroline) core. Another recent parameter for 4-coordinate complexes (τ₄, Yang et al., 2007) has been developed to place a structure on the continuum between square planar (0) and tetrahedral (1). For the present structure this value is 0.546.

Copper forms a similar complex with phendione. However, in this case the twofold axis passes between the phendione ligands with a dihedral angle of 44.5° between them.

In the structure of (I), there are weak C—H···O(phendione) and C—H···F(BF₄^-) interactions (Fig. 2).

Related literature top

For the different coordination properties of phendione, see: Calderazzo et al. (1999, 2002); Calucci et al. (2006); Galet et al. (2005); Lei et al. (1996); Okamura et al. (2006). For examples with phendione ligands where N and O donors are used simultaneously, see: Fox et al. (1991); Shavaleev et al. (2003a,b); Ruiz et al. (1999); Paw & Eisenberg (1997). Similar structures containing Ag have also been reported by Onuegbu et al. (2007). For background to phendione chemistry, see: Udeochu et al. (2007); Onuegbu et al. (2007). For reference structural data, see: Allen (2002); Leschke et al. (2002); Paramonov et al. (2003); Pallenberg et al. (1997); Titze et al. (1997). Details of the τ₄ parameter were given by Yang et al. (2007).

Experimental top

A flask containing 1,10-phenanthroline hydrate (1.00 g, 5.04 mmol) and potassium bromide (5.95 g, 50.0 mmol) was placed in an ice bath. Concentrated sulfuric acid (20 cm³) was added in small portions, followed by drop-wise addition of concentrated nitric acid (10 cm³). The resulting solution was heated for 2 h at 253–257 K and cooled to room temperature. The solution was then poured into 400 cm³ of water and neutralized with sodium bicarbonate, after which the phendione was extracted with dichloromethane, and recrystallized using a methanol-water mixture.

The title compound was synthesized in an atmosphere saturated with N₂. To a solution of tetrakis(acetonitrile)silver(I)tetrafluoridoborate (0.0843 g) in 10 ml of CH₃CN, was added drop-wise a solution (10 ml) of CH₃CN containing 0.0492 g of phendione. The final yellowish solution was filtered and allowed to slowly evaporate yielding reddish brown crystals of the title compound suitable for X-ray studies.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 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. View of (I), [Ag(L)₂]⁺(BF₄)^-, showing the atom-labelling scheme. The C—H···F interaction is shown as a dashed line. Unlabeled atoms are related by -x, y, 1/2 - z. Displacement ellipsoids are drawn at the 20% probability level. Only the major component of the disordered anion is shown.
	Fig. 2. The molecular packing of (I) viewed approximately along the b axis. Dotted lines indicate the C—H···O and C—H···F interactions. Only the major component of the disordered anion is shown.

Bis(1,10-phenanthroline-5,6-dione-κ²N,N')silver(I) tetrafluoridoborate top

Crystal data top

[Ag(C₁₂H₆N₂O₂)₂]BF₄	F(000) = 1216
M_r = 615.06	D_x = 1.879 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5444 reflections
a = 13.2249 (6) Å	θ = 4.6–32.4°
b = 12.0115 (17) Å	µ = 1.01 mm⁻¹
c = 14.4338 (7) Å	T = 200 K
β = 108.481 (5)°	Prism, colorless
V = 2174.6 (3) Å³	0.44 × 0.37 × 0.28 mm
Z = 4

Data collection top

Oxford Diffraction Gemini R diffractometer	3647 independent reflections
Radiation source: fine-focus sealed tube	2306 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 10.5081 pixels mm^-1	θ_max = 32.5°, θ_min = 4.6°
ϕ and ω scans	h = −19→19
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −17→17
T_min = 0.856, T_max = 1.000	l = −16→21
11815 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.087P)²] where P = (F_o² + 2F_c²)/3
3647 reflections	(Δ/σ)_max < 0.001
204 parameters	Δρ_max = 1.81 e Å⁻³
32 restraints	Δρ_min = −1.39 e Å⁻³

Crystal data top

[Ag(C₁₂H₆N₂O₂)₂]BF₄	V = 2174.6 (3) Å³
M_r = 615.06	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 13.2249 (6) Å	µ = 1.01 mm⁻¹
b = 12.0115 (17) Å	T = 200 K
c = 14.4338 (7) Å	0.44 × 0.37 × 0.28 mm
β = 108.481 (5)°

Data collection top

Oxford Diffraction Gemini R diffractometer	3647 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	2306 reflections with I > 2σ(I)
T_min = 0.856, T_max = 1.000	R_int = 0.024
11815 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	32 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 0.98	Δρ_max = 1.81 e Å⁻³
3647 reflections	Δρ_min = −1.39 e Å⁻³
204 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	Occ. (<1)
Ag	0.5000	0.21159 (3)	0.2500	0.04327 (15)
O1	1.01490 (18)	0.3415 (2)	0.5002 (2)	0.0563 (7)
O2	0.99985 (17)	0.1301 (2)	0.56180 (17)	0.0507 (6)
N1	0.65530 (18)	0.3220 (2)	0.29553 (17)	0.0304 (5)
N2	0.64367 (17)	0.10772 (19)	0.35180 (17)	0.0284 (5)
C1	0.6565 (2)	0.4291 (3)	0.2713 (2)	0.0371 (6)
H1A	0.5941	0.4599	0.2261	0.044*
C2	0.7443 (2)	0.4976 (3)	0.3086 (2)	0.0413 (7)
H2A	0.7414	0.5742	0.2914	0.050*
C3	0.8357 (2)	0.4515 (3)	0.3713 (2)	0.0387 (7)
H3A	0.8980	0.4957	0.3966	0.046*
C4	0.8364 (2)	0.3402 (2)	0.39734 (19)	0.0294 (5)
C5	0.9324 (2)	0.2908 (2)	0.4662 (2)	0.0356 (6)
C6	0.9259 (2)	0.1693 (3)	0.4981 (2)	0.0329 (6)
C7	0.82541 (19)	0.1076 (2)	0.45309 (18)	0.0282 (5)
C8	0.8176 (2)	−0.0024 (3)	0.4776 (2)	0.0373 (7)
H8A	0.8766	−0.0393	0.5224	0.045*
C9	0.7227 (2)	−0.0579 (3)	0.4360 (2)	0.0404 (7)
H9A	0.7159	−0.1346	0.4489	0.048*
C10	0.6377 (2)	0.0010 (2)	0.3753 (2)	0.0370 (6)
H10A	0.5716	−0.0365	0.3489	0.044*
C12	0.7426 (2)	0.2784 (2)	0.35847 (19)	0.0255 (5)
C11	0.73725 (19)	0.1602 (2)	0.38786 (18)	0.0249 (5)
B	0.5000	0.7040 (2)	0.2500	0.060 (2)
F1A	0.4655 (3)	0.6438 (4)	0.3134 (3)	0.0308 (13)	0.406 (4)
F2A	0.4411 (3)	0.7977 (3)	0.2246 (4)	0.107 (3)	0.406 (4)
F3A	0.60395 (19)	0.7324 (4)	0.2940 (3)	0.113 (3)	0.406 (4)
F4A	0.4924 (4)	0.6425 (5)	0.1696 (3)	0.0439 (18)	0.406 (4)
F1B	0.5925 (6)	0.6663 (3)	0.2398 (12)	0.053 (4)*	0.094 (4)
F2B	0.5000	0.8168 (3)	0.2500	0.053 (4)*	0.189 (8)
F3B	0.4168 (8)	0.6665 (3)	0.1746 (7)	0.053 (4)*	0.094 (4)
F4B	0.4905 (13)	0.6663 (3)	0.3353 (5)	0.053 (4)*	0.094 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag	0.02050 (16)	0.0611 (3)	0.0386 (2)	0.000	−0.00431 (12)	0.000
O1	0.0270 (11)	0.0649 (16)	0.0674 (17)	−0.0135 (11)	0.0012 (11)	−0.0144 (14)
O2	0.0269 (10)	0.0765 (16)	0.0400 (12)	0.0105 (10)	−0.0016 (9)	0.0064 (12)
N1	0.0259 (11)	0.0366 (12)	0.0260 (11)	0.0005 (9)	0.0045 (9)	0.0018 (9)
N2	0.0236 (10)	0.0309 (12)	0.0281 (11)	−0.0015 (8)	0.0043 (8)	−0.0018 (9)
C1	0.0384 (14)	0.0394 (16)	0.0301 (14)	0.0047 (12)	0.0061 (12)	0.0040 (12)
C2	0.0499 (17)	0.0374 (16)	0.0387 (17)	−0.0061 (14)	0.0171 (14)	0.0010 (13)
C3	0.0368 (14)	0.0429 (17)	0.0407 (16)	−0.0119 (12)	0.0185 (13)	−0.0085 (13)
C4	0.0255 (12)	0.0387 (15)	0.0257 (12)	−0.0073 (11)	0.0104 (10)	−0.0074 (11)
C5	0.0234 (12)	0.0477 (17)	0.0352 (15)	−0.0040 (11)	0.0087 (11)	−0.0133 (13)
C6	0.0216 (11)	0.0519 (16)	0.0228 (12)	0.0036 (11)	0.0037 (9)	−0.0026 (12)
C7	0.0212 (11)	0.0392 (15)	0.0235 (12)	0.0050 (10)	0.0062 (9)	−0.0006 (10)
C8	0.0347 (14)	0.0453 (17)	0.0332 (15)	0.0138 (12)	0.0126 (12)	0.0056 (12)
C9	0.0442 (16)	0.0338 (15)	0.0457 (18)	0.0038 (13)	0.0180 (14)	0.0061 (13)
C10	0.0335 (13)	0.0398 (16)	0.0400 (16)	−0.0065 (12)	0.0150 (12)	−0.0032 (12)
C12	0.0219 (11)	0.0349 (14)	0.0197 (11)	−0.0028 (9)	0.0067 (9)	−0.0035 (10)
C11	0.0207 (10)	0.0310 (13)	0.0218 (11)	0.0015 (10)	0.0048 (8)	−0.0027 (10)
B	0.110 (6)	0.009 (2)	0.085 (5)	0.000	0.065 (5)	0.000
F1A	0.032 (3)	0.036 (3)	0.022 (2)	−0.022 (2)	0.006 (2)	−0.0135 (18)
F2A	0.189 (9)	0.027 (3)	0.124 (7)	0.049 (3)	0.077 (6)	0.031 (3)
F3A	0.141 (7)	0.044 (4)	0.170 (8)	−0.033 (4)	0.071 (6)	−0.051 (5)
F4A	0.046 (4)	0.051 (3)	0.027 (3)	0.023 (3)	0.001 (2)	0.003 (2)

Geometric parameters (Å, º) top

Ag—N1	2.356 (2)	C5—C6	1.541 (5)
Ag—N1ⁱ	2.356 (2)	C6—C7	1.480 (4)
Ag—N2ⁱ	2.357 (2)	C7—C8	1.381 (4)
Ag—N2	2.357 (2)	C7—C11	1.396 (3)
O1—C5	1.210 (4)	C8—C9	1.379 (4)
O2—C6	1.206 (3)	C8—H8A	0.9500
N1—C12	1.329 (3)	C9—C10	1.380 (4)
N1—C1	1.335 (4)	C9—H9A	0.9500
N2—C10	1.335 (4)	C10—H10A	0.9500
N2—C11	1.338 (3)	C12—C11	1.489 (4)
C1—C2	1.385 (4)	B—F1A	1.354 (2)
C1—H1A	0.9500	B—F2A	1.352 (2)
C2—C3	1.377 (4)	B—F3A	1.362 (2)
C2—H2A	0.9500	B—F4A	1.352 (2)
C3—C4	1.389 (4)	B—F1B	1.355 (2)
C3—H3A	0.9500	B—F2B	1.355 (2)
C4—C12	1.402 (4)	B—F3B	1.356 (2)
C4—C5	1.466 (4)	B—F4B	1.355 (2)

N1—Ag—N1ⁱ	111.52 (12)	C8—C7—C11	119.5 (2)
N1—Ag—N2ⁱ	158.56 (8)	C8—C7—C6	119.8 (3)
N1ⁱ—Ag—N2ⁱ	70.42 (8)	C11—C7—C6	120.7 (2)
N1—Ag—N2	70.42 (8)	C9—C8—C7	118.8 (3)
N1ⁱ—Ag—N2	158.56 (8)	C9—C8—H8A	120.6
N2ⁱ—Ag—N2	116.08 (11)	C7—C8—H8A	120.6
C12—N1—C1	118.6 (2)	C8—C9—C10	118.3 (3)
C12—N1—Ag	117.40 (18)	C8—C9—H9A	120.8
C1—N1—Ag	123.46 (19)	C10—C9—H9A	120.8
C10—N2—C11	118.4 (2)	N2—C10—C9	123.5 (3)
C10—N2—Ag	124.49 (19)	N2—C10—H10A	118.3
C11—N2—Ag	117.15 (17)	C9—C10—H10A	118.3
N1—C1—C2	123.3 (3)	N1—C12—C4	122.1 (2)
N1—C1—H1A	118.3	N1—C12—C11	117.4 (2)
C2—C1—H1A	118.3	C4—C12—C11	120.4 (2)
C3—C2—C1	118.0 (3)	N2—C11—C7	121.4 (2)
C3—C2—H2A	121.0	N2—C11—C12	117.4 (2)
C1—C2—H2A	121.0	C7—C11—C12	121.2 (2)
C2—C3—C4	119.6 (3)	F2A—B—F4A	110.07 (10)
C2—C3—H3A	120.2	F2A—B—F1A	109.81 (10)
C4—C3—H3A	120.2	F4A—B—F1A	109.81 (9)
C3—C4—C12	118.2 (3)	F1A—B—F1B	113.8 (5)
C3—C4—C5	120.2 (2)	F2B—B—F1B	109.52 (10)
C12—C4—C5	121.6 (3)	F2A—B—F4B	108.2 (5)
O1—C5—C4	123.2 (3)	F2B—B—F4B	109.52 (10)
O1—C5—C6	119.0 (3)	F1B—B—F4B	109.52 (10)
C4—C5—C6	117.9 (2)	F4Aⁱ—B—F3B	109.1 (6)
O2—C6—C7	122.5 (3)	F2B—B—F3B	109.43 (10)
O2—C6—C5	119.3 (3)	F1B—B—F3B	109.43 (10)
C7—C6—C5	118.1 (2)	F4B—B—F3B	109.41 (10)

N1ⁱ—Ag—N1—C12	152.8 (2)	O2—C6—C7—C11	172.5 (3)
N2ⁱ—Ag—N1—C12	−116.1 (2)	C5—C6—C7—C11	−3.7 (4)
N2—Ag—N1—C12	−4.37 (18)	C11—C7—C8—C9	0.6 (4)
N1ⁱ—Ag—N1—C1	−18.6 (2)	C6—C7—C8—C9	178.9 (3)
N2ⁱ—Ag—N1—C1	72.5 (3)	C7—C8—C9—C10	−3.2 (4)
N2—Ag—N1—C1	−175.8 (2)	C11—N2—C10—C9	1.0 (4)
N1—Ag—N2—C10	−176.9 (3)	Ag—N2—C10—C9	−179.2 (2)
N1ⁱ—Ag—N2—C10	83.9 (3)	C8—C9—C10—N2	2.5 (5)
N2ⁱ—Ag—N2—C10	−19.1 (2)	C1—N1—C12—C4	−2.2 (4)
N1—Ag—N2—C11	2.92 (18)	Ag—N1—C12—C4	−174.04 (19)
N1ⁱ—Ag—N2—C11	−96.3 (3)	C1—N1—C12—C11	177.1 (2)
N2ⁱ—Ag—N2—C11	160.7 (2)	Ag—N1—C12—C11	5.3 (3)
C12—N1—C1—C2	−0.2 (4)	C3—C4—C12—N1	2.4 (4)
Ag—N1—C1—C2	171.1 (2)	C5—C4—C12—N1	−179.6 (2)
N1—C1—C2—C3	2.2 (5)	C3—C4—C12—C11	−176.9 (2)
C1—C2—C3—C4	−2.0 (4)	C5—C4—C12—C11	1.1 (4)
C2—C3—C4—C12	−0.2 (4)	C10—N2—C11—C7	−3.7 (4)
C2—C3—C4—C5	−178.3 (3)	Ag—N2—C11—C7	176.42 (18)
C3—C4—C5—O1	−2.8 (5)	C10—N2—C11—C12	178.4 (2)
C12—C4—C5—O1	179.2 (3)	Ag—N2—C11—C12	−1.4 (3)
C3—C4—C5—C6	175.6 (3)	C8—C7—C11—N2	3.0 (4)
C12—C4—C5—C6	−2.4 (4)	C6—C7—C11—N2	−175.3 (2)
O1—C5—C6—O2	5.7 (5)	C8—C7—C11—C12	−179.3 (2)
C4—C5—C6—O2	−172.7 (3)	C6—C7—C11—C12	2.4 (4)
O1—C5—C6—C7	−177.9 (3)	N1—C12—C11—N2	−2.6 (4)
C4—C5—C6—C7	3.6 (4)	C4—C12—C11—N2	176.7 (2)
O2—C6—C7—C8	−5.8 (4)	N1—C12—C11—C7	179.5 (2)
C5—C6—C7—C8	178.0 (3)	C4—C12—C11—C7	−1.1 (4)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O1ⁱⁱ	0.95	2.51	3.347 (4)	147
C1—H1A···F1Aⁱ	0.95	2.35	3.083 (6)	133
C2—H2A···F1B	0.95	2.17	2.803 (8)	123
C10—H10A···F2Aⁱⁱⁱ	0.95	2.24	2.859 (5)	122
C10—H10A···F2B^iv	0.95	2.28	3.065 (4)	140

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

Experimental details

Crystal data
Chemical formula	[Ag(C₁₂H₆N₂O₂)₂]BF₄
M_r	615.06
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	200
a, b, c (Å)	13.2249 (6), 12.0115 (17), 14.4338 (7)
β (°)	108.481 (5)
V (Å³)	2174.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.01
Crystal size (mm)	0.44 × 0.37 × 0.28

Data collection
Diffractometer	Oxford Diffraction Gemini R diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.856, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	11815, 3647, 2306
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.756

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.134, 0.98
No. of reflections	3647
No. of parameters	204
No. of restraints	32
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.81, −1.39

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Ag—N1

2.356 (2)

Ag—N2

2.357 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O1ⁱ	0.95	2.51	3.347 (4)	147.4
C1—H1A···F1Aⁱⁱ	0.95	2.35	3.083 (6)	133.1
C2—H2A···F1B	0.95	2.17	2.803 (8)	122.6
C10—H10A···F2Aⁱⁱⁱ	0.95	2.24	2.859 (5)	122.2
C10—H10A···F2B^iv	0.95	2.28	3.065 (4)	140.0

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

Acknowledgements

RJB acknowledges the NSF–MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.

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