Poly[[μ-ethane-1,2-diyl bis-(pyridine-3-carboxyl-ate)](μ-tetra-fluorido-borato)silver(I)].

In the title compound, [Ag(BF(4))(C(14)H(12)N(2)O(4))](n), the coordination of the Ag(+) ion is trigonal-bipyramidal with the N atoms of two ethane-1,2-diyl bis-(pyridine-3-carboxyl-ate) ligands in the apical positions and three F atoms belonging to different tetra-fluorido-borate anions in the equatorial plane. The material consists of infinite chains of [Ag(C(14)H(12)N(2)O(4))] units running along [001], held together by BF(4) (-) bridging anions.

Related literature

For the crystal structure of the ethane-1,2-diyl bis­(pyridine-3-carboxyl­ate) ligand, see: Brito et al. (2010 ▶). For background to coordination chemistry, see: Blake et al. (1999 ▶); Brito et al. (2011 ▶).

Experimental

Crystal data

[Ag(BF4)(C14H12N2O4)]

M = 466.94

Orthorhombic,

a = 15.2667 (11) Å

b = 6.7170 (4) Å

c = 30.8598 (16) Å

V = 3164.6 (3) Å3

Z = 8

Mo Kα radiation

μ = 1.34 mm−1

T = 173 K

0.16 × 0.04 × 0.04 mm

Data collection

Stoe IPDS-II two-circle diffractometer

Absorption correction: multi-scan (MULABS; Spek, 2009 ▶; Blessing, 1995 ▶) T min = 0.814, T max = 0.948

27909 measured reflections

2772 independent reflections

1605 reflections with I > 2σ(I)

R int = 0.115

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.144

S = 0.93

2772 reflections

235 parameters

H-atom parameters constrained

Δρmax = 1.75 e Å−3

Δρmin = −1.14 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812018399/ff2064sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018399/ff2064Isup2.hkl

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

[Ag(BF4)(C14H12N2O4)]	F(000) = 1840
Mr = 466.94	Dx = 1.960 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9495 reflections
a = 15.2667 (11) Å	θ = 2.7–25.9°
b = 6.7170 (4) Å	µ = 1.34 mm−1
c = 30.8598 (16) Å	T = 173 K
V = 3164.6 (3) Å3	Needle, colourless
Z = 8	0.16 × 0.04 × 0.04 mm

Stoe IPDS-II two-circle diffractometer	2772 independent reflections
Radiation source: fine-focus sealed tube	1605 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.115
ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −18→18
Tmin = 0.814, Tmax = 0.948	k = −7→7
27909 measured reflections	l = −36→36

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H-atom parameters constrained
S = 0.93	w = 1/[σ2(Fo2) + (0.0668P)2] where P = (Fo2 + 2Fc2)/3
2772 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 1.75 e Å−3
0 restraints	Δρmin = −1.14 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
Ag1	0.32630 (5)	0.68683 (11)	0.122155 (18)	0.0436 (2)
O1	0.1384 (4)	0.6081 (9)	0.27974 (18)	0.0388 (14)
O2	0.2325 (3)	0.4748 (8)	0.32836 (16)	0.0318 (13)
O3	0.1274 (4)	0.7200 (9)	0.46953 (18)	0.0426 (15)
O4	0.2171 (3)	0.6095 (9)	0.41696 (16)	0.0350 (13)
C1	0.2118 (6)	0.5608 (13)	0.2904 (2)	0.0318 (19)
C2	0.1594 (5)	0.4311 (13)	0.3564 (2)	0.0347 (19)
H2A	0.1715	0.3060	0.3723	0.042*
H2B	0.1065	0.4096	0.3385	0.042*
C3	0.1415 (5)	0.5929 (15)	0.3883 (2)	0.038 (2)
H3A	0.1317	0.7205	0.3730	0.046*
H3B	0.0884	0.5611	0.4054	0.046*
C4	0.1992 (5)	0.6804 (12)	0.4566 (2)	0.0305 (17)
N11	0.3421 (4)	0.6597 (11)	0.1910 (2)	0.0385 (17)
C12	0.2759 (6)	0.6318 (12)	0.2184 (2)	0.035 (2)
H12	0.2174	0.6408	0.2080	0.041*
C13	0.2907 (5)	0.5899 (12)	0.2618 (2)	0.0287 (17)
C14	0.3766 (5)	0.5786 (12)	0.2780 (3)	0.0310 (18)
H14	0.3881	0.5471	0.3074	0.037*
C15	0.4436 (5)	0.6155 (12)	0.2490 (3)	0.036 (2)
H15	0.5027	0.6141	0.2586	0.044*
C16	0.4251 (6)	0.6540 (14)	0.2065 (3)	0.042 (2)
H16	0.4723	0.6777	0.1871	0.050*
C21	0.2811 (5)	0.7043 (13)	0.4833 (2)	0.0295 (17)
C22	0.2702 (6)	0.7513 (12)	0.5268 (2)	0.032 (2)
H22	0.2126	0.7616	0.5382	0.039*
N23	0.3379 (5)	0.7822 (10)	0.5529 (2)	0.0384 (17)
C24	0.4197 (6)	0.7680 (13)	0.5363 (3)	0.041 (2)
H24	0.4682	0.7907	0.5549	0.049*
C25	0.4354 (6)	0.7217 (14)	0.4934 (3)	0.040 (2)
H25	0.4936	0.7149	0.4827	0.048*
C26	0.3651 (5)	0.6855 (13)	0.4662 (2)	0.0332 (17)
H26	0.3739	0.6490	0.4367	0.040*
B1	0.0651 (6)	0.6709 (18)	0.1252 (3)	0.040 (2)
F1	0.0369 (5)	0.8388 (12)	0.1072 (3)	0.107 (3)
F2	0.1447 (5)	0.6209 (11)	0.1101 (3)	0.098 (3)
F3	0.0720 (6)	0.7014 (14)	0.1693 (2)	0.110 (3)
F4	0.0034 (5)	0.5200 (11)	0.1204 (3)	0.097 (2)

	U11	U22	U33	U12	U13	U23
Ag1	0.0429 (4)	0.0680 (5)	0.0198 (3)	−0.0014 (4)	−0.0011 (3)	0.0042 (3)
O1	0.021 (3)	0.065 (4)	0.030 (3)	−0.002 (3)	−0.003 (2)	0.007 (3)
O2	0.030 (3)	0.046 (4)	0.019 (3)	−0.002 (2)	0.003 (2)	0.003 (2)
O3	0.026 (3)	0.068 (4)	0.033 (3)	0.005 (3)	0.003 (3)	−0.012 (3)
O4	0.029 (3)	0.059 (4)	0.018 (3)	−0.002 (2)	−0.002 (2)	−0.002 (2)
C1	0.035 (5)	0.040 (5)	0.020 (4)	−0.003 (4)	−0.003 (3)	−0.001 (4)
C2	0.032 (5)	0.054 (5)	0.017 (4)	−0.009 (4)	0.006 (3)	−0.001 (4)
C3	0.024 (4)	0.067 (6)	0.024 (4)	−0.003 (4)	−0.004 (3)	−0.010 (4)
C4	0.040 (5)	0.033 (4)	0.018 (3)	−0.004 (4)	0.000 (3)	−0.006 (4)
N11	0.036 (4)	0.053 (5)	0.026 (3)	−0.002 (4)	0.004 (3)	0.000 (3)
C12	0.030 (4)	0.050 (6)	0.024 (4)	0.004 (4)	−0.002 (3)	−0.003 (4)
C13	0.025 (4)	0.040 (5)	0.021 (4)	−0.002 (3)	0.003 (3)	−0.004 (3)
C14	0.032 (5)	0.039 (5)	0.022 (4)	−0.001 (4)	−0.002 (3)	0.001 (4)
C15	0.030 (5)	0.054 (5)	0.025 (4)	−0.001 (3)	−0.002 (4)	−0.002 (4)
C16	0.029 (4)	0.069 (7)	0.027 (4)	−0.001 (4)	0.006 (3)	−0.002 (4)
C21	0.025 (4)	0.044 (5)	0.019 (3)	0.002 (4)	0.001 (3)	0.000 (4)
C22	0.031 (5)	0.047 (6)	0.018 (4)	−0.001 (3)	0.001 (3)	0.002 (3)
N23	0.034 (4)	0.051 (4)	0.030 (3)	0.001 (3)	0.000 (3)	0.002 (3)
C24	0.030 (5)	0.065 (7)	0.029 (4)	−0.003 (4)	−0.005 (4)	−0.001 (4)
C25	0.028 (5)	0.063 (7)	0.030 (5)	0.004 (4)	−0.004 (4)	−0.006 (4)
C26	0.040 (4)	0.042 (5)	0.017 (4)	0.001 (4)	0.001 (3)	−0.002 (4)
B1	0.028 (4)	0.058 (6)	0.034 (5)	0.011 (5)	0.006 (4)	−0.003 (5)
F1	0.071 (5)	0.122 (7)	0.127 (7)	0.029 (5)	0.007 (5)	0.055 (5)
F2	0.057 (4)	0.103 (6)	0.136 (7)	0.016 (4)	0.042 (4)	0.000 (4)
F3	0.118 (6)	0.166 (7)	0.044 (4)	−0.038 (6)	0.003 (4)	−0.018 (5)
F4	0.079 (5)	0.118 (6)	0.095 (5)	−0.046 (4)	0.005 (4)	−0.025 (5)

Ag1—N11	2.145 (6)	C13—C14	1.405 (11)
Ag1—N23i	2.155 (6)	C14—C15	1.382 (11)
Ag1—F1ii	3.168 (9)	C14—H14	0.9500
Ag1—F2	2.832 (8)	C15—C16	1.365 (11)
Ag1—F2iii	2.972 (7)	C15—H15	0.9500
O1—C1	1.210 (9)	C16—H16	0.9500
O2—C1	1.345 (9)	C21—C22	1.389 (10)
O2—C2	1.443 (9)	C21—C26	1.394 (11)
O3—C4	1.196 (9)	C22—N23	1.327 (10)
O4—C4	1.341 (9)	C22—H22	0.9500
O4—C3	1.458 (9)	N23—C24	1.352 (11)
C1—C13	1.504 (11)	N23—Ag1iv	2.155 (6)
C2—C3	1.492 (12)	C24—C25	1.382 (12)
C2—H2A	0.9900	C24—H24	0.9500
C2—H2B	0.9900	C25—C26	1.383 (12)
C3—H3A	0.9900	C25—H25	0.9500
C3—H3B	0.9900	C26—H26	0.9500
C4—C21	1.506 (10)	B1—F1	1.329 (13)
N11—C12	1.332 (10)	B1—F2	1.344 (11)
N11—C16	1.356 (11)	B1—F3	1.379 (12)
C12—C13	1.389 (11)	B1—F4	1.391 (13)
C12—H12	0.9500
N11—Ag1—N23i	168.8 (3)	C13—C14—H14	121.5
C1—O2—C2	115.4 (6)	C16—C15—C14	120.1 (8)
C4—O4—C3	114.7 (6)	C16—C15—H15	119.9
O1—C1—O2	124.5 (7)	C14—C15—H15	119.9
O1—C1—C13	123.3 (7)	N11—C16—C15	122.6 (8)
O2—C1—C13	112.2 (7)	N11—C16—H16	118.7
O2—C2—C3	112.9 (7)	C15—C16—H16	118.7
O2—C2—H2A	109.0	C22—C21—C26	119.8 (7)
C3—C2—H2A	109.0	C22—C21—C4	117.0 (7)
O2—C2—H2B	109.0	C26—C21—C4	123.2 (6)
C3—C2—H2B	109.0	N23—C22—C21	121.9 (8)
H2A—C2—H2B	107.8	N23—C22—H22	119.0
O4—C3—C2	108.1 (7)	C21—C22—H22	119.0
O4—C3—H3A	110.1	C22—N23—C24	118.6 (7)
C2—C3—H3A	110.1	C22—N23—Ag1iv	123.5 (6)
O4—C3—H3B	110.1	C24—N23—Ag1iv	117.3 (5)
C2—C3—H3B	110.1	N23—C24—C25	122.7 (8)
H3A—C3—H3B	108.4	N23—C24—H24	118.7
O3—C4—O4	124.8 (7)	C25—C24—H24	118.7
O3—C4—C21	123.7 (7)	C24—C25—C26	119.1 (8)
O4—C4—C21	111.6 (6)	C24—C25—H25	120.4
C12—N11—C16	118.7 (7)	C26—C25—H25	120.4
C12—N11—Ag1	123.7 (5)	C25—C26—C21	117.9 (7)
C16—N11—Ag1	117.3 (5)	C25—C26—H26	121.1
N11—C12—C13	121.2 (8)	C21—C26—H26	121.1
N11—C12—H12	119.4	F1—B1—F2	111.1 (9)
C13—C12—H12	119.4	F1—B1—F3	108.1 (10)
C12—C13—C14	120.3 (7)	F2—B1—F3	108.0 (9)
C12—C13—C1	117.5 (7)	F1—B1—F4	110.8 (9)
C14—C13—C1	122.2 (7)	F2—B1—F4	113.1 (9)
C15—C14—C13	116.9 (7)	F3—B1—F4	105.3 (8)
C15—C14—H14	121.5
C2—O2—C1—O1	2.8 (11)	C13—C14—C15—C16	−2.1 (13)
C2—O2—C1—C13	−176.4 (6)	C12—N11—C16—C15	1.8 (14)
C1—O2—C2—C3	−93.6 (8)	Ag1—N11—C16—C15	−172.7 (7)
C4—O4—C3—C2	−152.9 (7)	C14—C15—C16—N11	0.6 (14)
O2—C2—C3—O4	−63.9 (9)	O3—C4—C21—C22	8.2 (13)
C3—O4—C4—O3	3.4 (12)	O4—C4—C21—C22	−171.7 (7)
C3—O4—C4—C21	−176.7 (7)	O3—C4—C21—C26	−170.4 (9)
N23i—Ag1—N11—C12	−177.4 (12)	O4—C4—C21—C26	9.7 (12)
N23i—Ag1—N11—C16	−3.2 (18)	C26—C21—C22—N23	1.0 (13)
C16—N11—C12—C13	−2.5 (12)	C4—C21—C22—N23	−177.7 (8)
Ag1—N11—C12—C13	171.6 (6)	C21—C22—N23—C24	0.2 (12)
N11—C12—C13—C14	0.9 (13)	C21—C22—N23—Ag1iv	−170.8 (6)
N11—C12—C13—C1	179.9 (8)	C22—N23—C24—C25	−0.3 (13)
O1—C1—C13—C12	−14.4 (12)	Ag1iv—N23—C24—C25	171.3 (7)
O2—C1—C13—C12	164.9 (7)	N23—C24—C25—C26	−1.0 (14)
O1—C1—C13—C14	164.7 (8)	C24—C25—C26—C21	2.1 (14)
O2—C1—C13—C14	−16.1 (11)	C22—C21—C26—C25	−2.2 (13)
C12—C13—C14—C15	1.4 (12)	C4—C21—C26—C25	176.4 (8)
C1—C13—C14—C15	−177.6 (8)

Table 1

Selected bond lengths (Å)

Ag1—N11	2.145 (6)
Ag1—N23i	2.155 (6)
Ag1—F1ii	3.168 (9)
Ag1—F2	2.832 (8)
Ag1—F2iii	2.972 (7)

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