Bis(1,10-phenanthroline-5,6-dione-κN,N')silver(I) tetra-fluoridoborate.

In the structure of the title compound, [Ag(C(12)H(6)N(2)O(2))(2)]BF(4) or [AgL(2)]BF(4) (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 tetra-hedral (τ(4) = 0.546). The crystal structure is consolidated by weak C-H⋯O(phendione) and C-H⋯F(BF(4) (-)) inter-actions. The BF(4) (-) 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. (2003 ▶); 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 = 615.06

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.134

S = 0.98

3647 reflections

204 parameters

32 restraints

H-atom parameters constrained

Δρmax = 1.81 e Å−3

Δρmin = −1.39 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680903222X/wm2249sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ag(C12H6N2O2)2]BF4	F(000) = 1216
Mr = 615.06	Dx = 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 = 1.00 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

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

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(Fo2) + (0.087P)2] where P = (Fo2 + 2Fc2)/3
3647 reflections	(Δ/σ)max < 0.001
204 parameters	Δρmax = 1.81 e Å−3
32 restraints	Δρmin = −1.39 e Å−3

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.

	x	y	z	Uiso*/Ueq	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)

	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)

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)

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···F2Biv	0.95	2.28	3.065 (4)	140

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⋯F2Biv	0.95	2.28	3.065 (4)	140

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .