Bis[2-(thio-phen-2-yl)quinoxaline-κN (4)]silver(I) tetra-fluoridoborate.

In the title compound, [Ag(C12H8N2S)2]BF4, the two-coordinate Ag(I) ion lies on a crystallographic inversion center and is linearly bonded to the N-donor atoms of two separate quinoxaline ligands. The thio-phenyl ring of the ligand is nearly coplanar with the quinoxaline ring system [dihedral angle = 9.15 (13)°]. In the crystal, the complex mol-ecules pack in layers parallel to (-102) and form weak π-π ring stacking inter-actions [minimum ring centroid separation = 3.7054 (17) Å]. The tetra-fluoridoroborate anion is equally disordered about an inversion center.

Related literature

For the synthesis of the title compound, see: Bhogala et al. (2003 ▶). For the structure of a similar compound, see: Wang (2012 ▶).

Experimental

Crystal data

[Ag(C12H8N2S)2]BF4

M = 619.21

Monoclinic,

a = 14.1249 (19) Å

b = 13.1972 (16) Å

c = 13.739 (2) Å

β = 102.991 (15)°

V = 2495.5 (6) Å3

Z = 4

Mo Kα radiation

μ = 1.03 mm−1

T = 293 K

0.32 × 0.22 × 0.17 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 CCD diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.657, T max = 1.000

30081 measured reflections

4624 independent reflections

2670 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.204

S = 0.93

4624 reflections

187 parameters

55 restraints

H-atom parameters constrained

Δρmax = 0.68 e Å−3

Δρmin = −0.51 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813004510/zs2248sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813004510/zs2248Isup2.hkl

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

[Ag(C12H8N2S)2]BF4	F(000) = 1232
Mr = 619.21	Dx = 1.648 Mg m−3
Monoclinic, C2/c	Melting point: 395 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 14.1249 (19) Å	Cell parameters from 7201 reflections
b = 13.1972 (16) Å	θ = 4.3–33.4°
c = 13.739 (2) Å	µ = 1.03 mm−1
β = 102.991 (15)°	T = 293 K
V = 2495.5 (6) Å3	Plate, white
Z = 4	0.32 × 0.22 × 0.17 mm

Oxford Diffraction Xcalibur Sapphire3 CCD diffractometer	4624 independent reflections
Radiation source: fine-focus sealed tube	2670 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
Detector resolution: 16.1790 pixels mm-1	θmax = 33.4°, θmin = 4.3°
ω scans	h = −21→21
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −20→20
Tmin = 0.657, Tmax = 1.000	l = −21→20
30081 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.204	H-atom parameters constrained
S = 0.93	w = 1/[σ2(Fo2) + (0.1425P)2] where P = (Fo2 + 2Fc2)/3
4624 reflections	(Δ/σ)max < 0.001
187 parameters	Δρmax = 0.68 e Å−3
55 restraints	Δρmin = −0.51 e Å−3

Experimental. Hydrogen atoms were included in calculated positions with a C—H distance of 0.93 Å and were included in the refinement in a riding motion approximation with Uiso = 1.2Ueq of the carrier atom.

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)
Ag1	1.2500	0.2500	0.5000	0.0834 (2)
N1	1.11733 (17)	0.16642 (18)	0.44213 (18)	0.0522 (5)
C1	1.0346 (2)	0.2103 (2)	0.4009 (2)	0.0519 (6)
H1	1.0308	0.2806	0.4034	0.062*
C8	0.95133 (18)	0.15564 (19)	0.35281 (18)	0.0456 (5)
N2	0.95235 (14)	0.05545 (16)	0.34896 (15)	0.0439 (4)
C7	1.03648 (17)	0.00867 (19)	0.39162 (17)	0.0423 (5)
C2	1.12040 (17)	0.0612 (2)	0.43877 (18)	0.0457 (5)
C3	1.2080 (2)	0.0087 (3)	0.4793 (2)	0.0599 (7)
H3	1.2637	0.0441	0.5099	0.072*
C4	1.2094 (2)	−0.0938 (3)	0.4727 (3)	0.0680 (8)
H4	1.2666	−0.1288	0.4990	0.082*
C5	1.1263 (3)	−0.1472 (2)	0.4270 (3)	0.0661 (8)
H5	1.1289	−0.2175	0.4234	0.079*
C6	1.0418 (2)	−0.0988 (2)	0.3877 (2)	0.0527 (6)
H6	0.9870	−0.1360	0.3581	0.063*
S1	0.76065 (6)	0.13484 (8)	0.25355 (7)	0.0682 (3)
C9	0.8619 (2)	0.2074 (2)	0.3038 (2)	0.0526 (6)
C10	0.8465 (3)	0.3134 (3)	0.2847 (2)	0.0727 (10)
H10	0.8920	0.3644	0.3053	0.087*
C11	0.7490 (3)	0.3275 (3)	0.2284 (3)	0.0787 (11)
H11	0.7233	0.3909	0.2081	0.094*
C12	0.6976 (3)	0.2410 (3)	0.2073 (3)	0.0757 (11)
H12	0.6336	0.2394	0.1708	0.091*
B1	1.0011 (7)	0.5432 (7)	0.4307 (12)	0.174 (6)	0.50
F1	1.0535 (5)	0.4612 (6)	0.4342 (12)	0.234 (7)	0.50
F2	0.9766 (15)	0.5583 (11)	0.5186 (14)	0.405 (13)	0.50
F3	0.9165 (7)	0.5285 (7)	0.3685 (14)	0.331 (10)	0.50
F4	1.0358 (6)	0.6261 (5)	0.4077 (10)	0.244 (7)	0.50

	U11	U22	U33	U12	U13	U23
Ag1	0.0568 (2)	0.0772 (3)	0.1093 (4)	−0.03177 (17)	0.0040 (2)	−0.01481 (19)
N1	0.0466 (11)	0.0521 (12)	0.0570 (13)	−0.0126 (9)	0.0097 (9)	−0.0046 (9)
C1	0.0569 (15)	0.0423 (12)	0.0570 (15)	−0.0105 (11)	0.0137 (12)	−0.0031 (11)
C8	0.0446 (11)	0.0505 (13)	0.0422 (12)	−0.0028 (10)	0.0109 (9)	−0.0012 (10)
N2	0.0370 (9)	0.0493 (11)	0.0444 (11)	−0.0053 (8)	0.0070 (8)	−0.0035 (8)
C7	0.0390 (10)	0.0458 (12)	0.0432 (12)	−0.0061 (9)	0.0112 (9)	−0.0023 (9)
C2	0.0362 (10)	0.0539 (13)	0.0460 (12)	−0.0082 (9)	0.0073 (9)	0.0011 (10)
C3	0.0417 (13)	0.0758 (19)	0.0595 (16)	−0.0039 (12)	0.0059 (11)	0.0041 (14)
C4	0.0509 (16)	0.081 (2)	0.0702 (19)	0.0120 (15)	0.0093 (14)	0.0139 (16)
C5	0.072 (2)	0.0529 (15)	0.075 (2)	0.0122 (14)	0.0215 (17)	0.0108 (14)
C6	0.0554 (14)	0.0446 (13)	0.0563 (15)	−0.0060 (11)	0.0089 (12)	0.0045 (11)
S1	0.0499 (4)	0.0782 (6)	0.0718 (5)	0.0075 (3)	0.0036 (3)	0.0082 (4)
C9	0.0533 (14)	0.0571 (15)	0.0479 (14)	0.0086 (12)	0.0124 (11)	−0.0011 (12)
C10	0.079 (2)	0.082 (2)	0.0557 (17)	0.0280 (19)	0.0122 (16)	−0.0003 (15)
C11	0.085 (2)	0.076 (2)	0.075 (2)	0.032 (2)	0.0171 (19)	0.0093 (18)
C12	0.066 (2)	0.087 (3)	0.071 (2)	0.0307 (18)	0.0072 (17)	0.0093 (16)
B1	0.057 (5)	0.087 (6)	0.361 (17)	−0.015 (4)	0.015 (8)	−0.096 (9)
F1	0.063 (4)	0.091 (5)	0.53 (2)	−0.003 (3)	0.017 (7)	−0.064 (8)
F2	0.66 (4)	0.145 (10)	0.48 (2)	−0.088 (16)	0.29 (2)	−0.150 (14)
F3	0.130 (7)	0.121 (7)	0.64 (3)	−0.002 (5)	−0.133 (11)	−0.059 (11)
F4	0.125 (6)	0.077 (4)	0.55 (2)	−0.037 (4)	0.123 (10)	−0.048 (7)

Ag1—N1	2.166 (2)	C5—C6	1.355 (4)
Ag1—N1i	2.166 (2)	C5—H5	0.9300
N1—C1	1.313 (4)	C6—H6	0.9300
N1—C2	1.391 (3)	S1—C12	1.705 (3)
C1—C8	1.411 (4)	S1—C9	1.731 (3)
C1—H1	0.9300	C9—C10	1.432 (5)
C8—N2	1.323 (3)	C10—C11	1.432 (6)
C8—C9	1.460 (4)	C10—H10	0.9300
N2—C7	1.350 (3)	C11—C12	1.349 (6)
C7—C2	1.400 (3)	C11—H11	0.9300
C7—C6	1.421 (4)	C12—H12	0.9300
C2—C3	1.418 (4)	B1—F4	1.267 (11)
C3—C4	1.357 (5)	B1—F1	1.307 (11)
C3—H3	0.9300	B1—F3	1.317 (11)
C4—C5	1.391 (5)	B1—F2	1.343 (13)
C4—H4	0.9300
N1—Ag1—N1i	179.998 (2)	C6—C5—H5	119.4
C1—N1—C2	117.2 (2)	C4—C5—H5	119.4
C1—N1—Ag1	123.11 (18)	C5—C6—C7	120.3 (3)
C2—N1—Ag1	119.34 (18)	C5—C6—H6	119.8
N1—C1—C8	122.9 (3)	C7—C6—H6	119.8
N1—C1—H1	118.5	C12—S1—C9	90.6 (2)
C8—C1—H1	118.5	C10—C9—C8	128.5 (3)
N2—C8—C1	120.9 (2)	C10—C9—S1	112.9 (2)
N2—C8—C9	117.7 (2)	C8—C9—S1	118.5 (2)
C1—C8—C9	121.4 (2)	C9—C10—C11	108.3 (4)
C8—N2—C7	117.1 (2)	C9—C10—H10	125.8
N2—C7—C2	123.1 (2)	C11—C10—H10	125.8
N2—C7—C6	119.3 (2)	C12—C11—C10	114.4 (4)
C2—C7—C6	117.7 (2)	C12—C11—H11	122.8
N1—C2—C7	118.7 (2)	C10—C11—H11	122.8
N1—C2—C3	120.3 (2)	C11—C12—S1	113.8 (3)
C7—C2—C3	120.9 (3)	C11—C12—H12	123.1
C4—C3—C2	119.0 (3)	S1—C12—H12	123.1
C4—C3—H3	120.5	F4—B1—F1	118.4 (9)
C2—C3—H3	120.5	F4—B1—F3	108.1 (11)
C3—C4—C5	120.8 (3)	F1—B1—F3	109.0 (9)
C3—C4—H4	119.6	F4—B1—F2	106.8 (10)
C5—C4—H4	119.6	F1—B1—F2	110.4 (12)
C6—C5—C4	121.3 (3)	F3—B1—F2	103.0 (10)