2,5-Bis(pyridinium-2-yl)-3,6-bis-(2-pyrid-yl)pyrazine bis-[tetra-chlorido-aurate(III)].

In the title compound, (C(24)H(18)N(6))[AuCl(4)](2), the cation is located on an inversion center. Each of the two independent Au(III) ions lies on an inversion center and has a distorted square-planar geometry. In the crystal, inter-molecular C-H⋯Cl hydrogen bonds, π-π inter-actions [centroid-centroid distances = 3.5548 (16) and 3.7507 (16) Å] and Au⋯π inter-actions [Au⋯centroid distance = 3.6424 (10) Å] are effective in the stabilization of the structure, resulting in the formation of a supra-molecular structure. Intra-molecular N-H⋯N hydrogen bonds are present in the cation.

Related literature

For the structures of related proton-transfer complexes, see: Abedi et al. (2008 ▶); Aragoni et al. (2005a ▶,b ▶); Bock et al. (1992 ▶); Calleja et al. (2001 ▶); Graf & Stoeckli-Evans (1996 ▶); Hasan et al. (1999 ▶); Hojjat Kashani et al. (2008 ▶); Johnson & Steed (1998 ▶); Kalateh et al. (2008 ▶); Padgett et al. (2005 ▶); Yap et al. (1995 ▶); Yıldırım et al. (2009a ▶,b ▶); Zhang et al. (2006 ▶).

Experimental

Crystal data

(C24H18N6)[AuCl4]2

M = 1067.98

Triclinic,

a = 7.2847 (6) Å

b = 9.6611 (8) Å

c = 10.6263 (9) Å

α = 79.6692 (13)°

β = 78.7378 (12)°

γ = 88.8600 (13)°

V = 721.48 (10) Å3

Z = 1

Mo Kα radiation

μ = 10.93 mm−1

T = 100 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.080, T max = 0.110

8652 measured reflections

3821 independent reflections

3395 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.019

wR(F 2) = 0.050

S = 1.05

3821 reflections

185 parameters

H-atom parameters constrained

Δρmax = 1.76 e Å−3

Δρmin = −1.36 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536811036208/hy2466sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036208/hy2466Isup2.hkl

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

(C24H18N6)[AuCl4]2	Z = 1
Mr = 1067.98	F(000) = 498
Triclinic, P1	Dx = 2.458 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2847 (6) Å	Cell parameters from 336 reflections
b = 9.6611 (8) Å	θ = 3.0–29.0°
c = 10.6263 (9) Å	µ = 10.93 mm−1
α = 79.6692 (13)°	T = 100 K
β = 78.7378 (12)°	Prism, yellow
γ = 88.8600 (13)°	0.30 × 0.20 × 0.20 mm
V = 721.48 (10) Å3

Bruker APEXII CCD diffractometer	3821 independent reflections
Radiation source: fine-focus sealed tube	3395 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 29.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.080, Tmax = 0.110	k = −13→13
8652 measured reflections	l = −14→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.019	H-atom parameters constrained
wR(F2) = 0.050	w = 1/[σ2(Fo2) + (0.0278P)2 + 0.1485P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.003
3821 reflections	Δρmax = 1.76 e Å−3
185 parameters	Δρmin = −1.36 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0137 (4)

	x	y	z	Uiso*/Ueq
N1	0.4305 (3)	0.3824 (2)	0.5837 (2)	0.0090 (4)
N2	0.4962 (3)	0.2025 (2)	0.3140 (2)	0.0103 (4)
H2N	0.5714	0.2659	0.2616	0.012*
N3	0.3379 (3)	0.5836 (2)	0.8362 (2)	0.0102 (4)
C1	0.4712 (3)	0.3792 (3)	0.4559 (2)	0.0095 (5)
C2	0.4559 (3)	0.4976 (3)	0.6317 (2)	0.0091 (5)
C3	0.4186 (3)	0.2409 (3)	0.4284 (2)	0.0084 (5)
C4	0.4503 (4)	0.0810 (3)	0.2834 (3)	0.0125 (5)
H4A	0.5062	0.0580	0.2014	0.015*
C5	0.3216 (4)	−0.0119 (3)	0.3702 (3)	0.0126 (5)
H5A	0.2882	−0.0979	0.3483	0.015*
C6	0.2435 (4)	0.0241 (3)	0.4889 (3)	0.0130 (5)
H6A	0.1563	−0.0380	0.5503	0.016*
C7	0.2919 (4)	0.1504 (3)	0.5190 (3)	0.0117 (5)
H6B	0.2388	0.1749	0.6009	0.014*
C8	0.3936 (3)	0.4731 (3)	0.7766 (2)	0.0092 (5)
C9	0.2659 (4)	0.5627 (3)	0.9642 (3)	0.0136 (5)
H8A	0.2255	0.6416	1.0038	0.016*
C10	0.2484 (4)	0.4302 (3)	1.0404 (3)	0.0135 (5)
H9A	0.1943	0.4174	1.1307	0.016*
C11	0.3120 (4)	0.3162 (3)	0.9817 (3)	0.0126 (5)
H10A	0.3062	0.2242	1.0323	0.015*
C12	0.3843 (4)	0.3378 (3)	0.8486 (2)	0.0127 (5)
H11A	0.4269	0.2605	0.8072	0.015*
Cl3	−0.10327 (10)	0.34900 (7)	0.69144 (6)	0.01701 (14)
Cl4	−0.05043 (9)	0.33137 (7)	0.38464 (6)	0.01462 (13)
Cl1	0.28009 (9)	0.92195 (7)	0.04725 (6)	0.01430 (13)
Cl2	0.05623 (9)	0.89691 (7)	−0.18017 (6)	0.01601 (14)
Au1	0.0000	1.0000	0.0000	0.00864 (5)
Au2	0.0000	0.5000	0.5000	0.00909 (5)

	U11	U22	U33	U12	U13	U23
N1	0.0094 (10)	0.0098 (10)	0.0087 (10)	0.0017 (8)	−0.0029 (8)	−0.0026 (8)
N2	0.0119 (10)	0.0098 (10)	0.0087 (10)	−0.0012 (8)	−0.0001 (8)	−0.0018 (8)
N3	0.0111 (10)	0.0103 (10)	0.0089 (10)	0.0001 (8)	−0.0009 (8)	−0.0023 (8)
C1	0.0094 (11)	0.0085 (11)	0.0107 (11)	0.0018 (9)	−0.0009 (9)	−0.0031 (9)
C2	0.0081 (11)	0.0096 (11)	0.0098 (11)	0.0019 (9)	−0.0014 (9)	−0.0032 (9)
C3	0.0090 (11)	0.0083 (11)	0.0086 (11)	0.0025 (9)	−0.0034 (9)	−0.0019 (9)
C4	0.0162 (13)	0.0105 (12)	0.0113 (12)	0.0011 (10)	−0.0021 (10)	−0.0043 (10)
C5	0.0172 (13)	0.0078 (11)	0.0136 (12)	−0.0004 (10)	−0.0046 (10)	−0.0021 (10)
C6	0.0140 (13)	0.0108 (12)	0.0139 (13)	−0.0018 (10)	−0.0037 (10)	−0.0004 (10)
C7	0.0125 (12)	0.0122 (12)	0.0098 (12)	0.0016 (10)	−0.0004 (10)	−0.0029 (10)
C8	0.0089 (11)	0.0113 (12)	0.0072 (11)	−0.0009 (9)	−0.0004 (9)	−0.0027 (9)
C9	0.0172 (13)	0.0136 (13)	0.0101 (12)	−0.0016 (10)	−0.0001 (10)	−0.0053 (10)
C10	0.0161 (13)	0.0160 (13)	0.0079 (11)	−0.0018 (10)	−0.0005 (10)	−0.0024 (10)
C11	0.0160 (13)	0.0112 (12)	0.0103 (12)	−0.0026 (10)	−0.0023 (10)	−0.0007 (10)
C12	0.0177 (13)	0.0111 (12)	0.0091 (12)	0.0010 (10)	−0.0014 (10)	−0.0024 (9)
Cl3	0.0223 (3)	0.0147 (3)	0.0120 (3)	−0.0025 (3)	0.0002 (3)	−0.0005 (2)
Cl4	0.0180 (3)	0.0130 (3)	0.0151 (3)	0.0005 (2)	−0.0051 (3)	−0.0063 (2)
Cl1	0.0133 (3)	0.0173 (3)	0.0133 (3)	0.0026 (2)	−0.0028 (2)	−0.0054 (2)
Cl2	0.0173 (3)	0.0215 (3)	0.0111 (3)	0.0019 (3)	−0.0008 (2)	−0.0103 (2)
Au1	0.01007 (8)	0.00904 (8)	0.00661 (8)	−0.00065 (5)	0.00033 (5)	−0.00288 (5)
Au2	0.00902 (8)	0.00935 (8)	0.00916 (8)	0.00064 (5)	−0.00137 (5)	−0.00284 (5)

N1—C2	1.335 (3)	C6—C7	1.384 (4)
N1—C1	1.338 (3)	C6—H6A	0.9500
N2—C4	1.338 (3)	C7—H6B	0.9500
N2—C3	1.349 (3)	C8—C12	1.387 (4)
N2—H2N	0.8705	C9—C10	1.380 (4)
N3—C9	1.339 (3)	C9—H8A	0.9500
N3—C8	1.353 (3)	C10—C11	1.389 (4)
C1—C2i	1.414 (4)	C10—H9A	0.9500
C1—C3	1.491 (3)	C11—C12	1.389 (3)
C2—C1i	1.414 (4)	C11—H10A	0.9500
C2—C8	1.494 (3)	C12—H11A	0.9500
C3—C7	1.388 (3)	Au1—Cl1	2.2775 (7)
C4—C5	1.391 (4)	Au1—Cl2	2.2774 (6)
C4—H4A	0.9500	Au2—Cl3	2.2834 (7)
C5—C6	1.381 (4)	Au2—Cl4	2.2821 (6)
C5—H5A	0.9500
C2—N1—C1	122.5 (2)	C3—C7—H6B	120.3
C4—N2—C3	121.8 (2)	N3—C8—C12	120.3 (2)
C4—N2—H2N	124.3	N3—C8—C2	119.3 (2)
C3—N2—H2N	113.8	C12—C8—C2	120.4 (2)
C9—N3—C8	120.3 (2)	N3—C9—C10	122.1 (3)
N1—C1—C2i	118.8 (2)	N3—C9—H8A	118.9
N1—C1—C3	111.4 (2)	C10—C9—H8A	118.9
C2i—C1—C3	129.6 (2)	C9—C10—C11	118.3 (2)
N1—C2—C1i	118.7 (2)	C9—C10—H9A	120.9
N1—C2—C8	111.2 (2)	C11—C10—H9A	120.9
C1i—C2—C8	130.0 (2)	C12—C11—C10	119.5 (2)
N2—C3—C7	119.4 (2)	C12—C11—H10A	120.2
N2—C3—C1	119.6 (2)	C10—C11—H10A	120.2
C7—C3—C1	121.0 (2)	C8—C12—C11	119.4 (2)
N2—C4—C5	120.8 (2)	C8—C12—H11A	120.3
N2—C4—H4A	119.6	C11—C12—H11A	120.3
C5—C4—H4A	119.6	Cl2ii—Au1—Cl2	180.0
C6—C5—C4	118.2 (2)	Cl2ii—Au1—Cl1	90.28 (2)
C6—C5—H5A	120.9	Cl2—Au1—Cl1	89.72 (2)
C4—C5—H5A	120.9	Cl1—Au1—Cl1ii	180.0
C5—C6—C7	120.3 (3)	Cl4iii—Au2—Cl4	180.000 (19)
C5—C6—H6A	119.9	Cl4iii—Au2—Cl3	89.50 (2)
C7—C6—H6A	119.9	Cl4—Au2—Cl3	90.50 (2)
C6—C7—C3	119.4 (2)	Cl3—Au2—Cl3iii	180.0
C6—C7—H6B	120.3
C2—N1—C1—C2i	0.1 (4)	N2—C3—C7—C6	−1.8 (4)
C2—N1—C1—C3	−176.5 (2)	C1—C3—C7—C6	178.7 (2)
C1—N1—C2—C1i	−0.1 (4)	C9—N3—C8—C12	−2.9 (4)
C1—N1—C2—C8	178.2 (2)	C9—N3—C8—C2	174.0 (2)
C4—N2—C3—C7	2.1 (4)	N1—C2—C8—N3	−153.8 (2)
C4—N2—C3—C1	−178.4 (2)	C1i—C2—C8—N3	24.3 (4)
N1—C1—C3—N2	−160.6 (2)	N1—C2—C8—C12	23.1 (3)
C2i—C1—C3—N2	23.3 (4)	C1i—C2—C8—C12	−158.8 (3)
N1—C1—C3—C7	19.0 (3)	C8—N3—C9—C10	1.2 (4)
C2i—C1—C3—C7	−157.2 (3)	N3—C9—C10—C11	1.5 (4)
C3—N2—C4—C5	−1.0 (4)	C9—C10—C11—C12	−2.4 (4)
N2—C4—C5—C6	−0.4 (4)	N3—C8—C12—C11	1.9 (4)
C4—C5—C6—C7	0.7 (4)	C2—C8—C12—C11	−174.9 (2)
C5—C6—C7—C3	0.4 (4)	C10—C11—C12—C8	0.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···N3i	0.87	1.69	2.538 (3)	164
C4—H4A···Cl1iv	0.95	2.77	3.680 (3)	161
C6—H6A···Cl2v	0.95	2.77	3.519 (3)	136

Table 1

Selected bond lengths (Å)

Au1—Cl1	2.2775 (7)
Au1—Cl2	2.2774 (6)
Au2—Cl3	2.2834 (7)
Au2—Cl4	2.2821 (6)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯N3i	0.87	1.69	2.538 (3)	164
C4—H4A⋯Cl1ii	0.95	2.77	3.680 (3)	161
C6—H6A⋯Cl2iii	0.95	2.77	3.519 (3)	136

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