2,5-Bis(pyridinium-2-yl)-3,6-bis­(2-pyrid­yl)pyrazine bis­[tetra­chlorido­aurate(III)]

Abedi, A.; Dabbaghi, A.; Amani, V.

doi:10.1107/S1600536811036208

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Pages m1375-m1376

https://doi.org/10.1107/S1600536811036208

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2,5-Bis(pyridinium-2-yl)-3,6-bis(2-pyridyl)pyrazine bis[tetrachloridoaurate(III)]

Anita Abedi,^a ^* Azra Dabbaghi ^a and Vahid Amani ^b

^aDepartment of Chemistry, North Tehran Branch, Islamic Azad University, Tehran, Iran, and ^bDepartment of Chemistry, Share-Ray Branch, Islamic Azad University, Tehran, Iran
^*Correspondence e-mail: anita_abedi@yahoo.com

(Received 20 August 2011; accepted 5 September 2011; online 14 September 2011)

In the title compound, (C₂₄H₁₈N₆)[AuCl₄]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, intermolecular C—H⋯Cl hydrogen bonds, π–π interactions [centroid–centroid distances = 3.5548 (16) and 3.7507 (16) Å] and Au⋯π interactions [Au⋯centroid distance = 3.6424 (10) Å] are effective in the stabilization of the structure, resulting in the formation of a supramolecular structure. Intramolecular 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_r = 1067.98
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.019
wR(F²) = 0.050
S = 1.05
3821 reflections
185 parameters
H-atom parameters constrained
Δρ_max = 1.76 e Å⁻³
Δρ_min = −1.36 e Å⁻³

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) -x+1, -y+1, -z+1; (ii) -x+1, -y+1, -z; (iii) x, y-1, z+1.

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.

Supporting information

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S1600536811036208/hy2466sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811036208/hy2466Isup2.hkl

checkCIF report

Comment top

Recently, we reported the synthesis and crystal structures of two proton-transfer complexes (Abedi et al., 2008; Kalateh et al., 2008). Several proton-transfer systems using 2,3,5,6-tetrakis(2-pyridyl)pyrazine (tppz) as proton donor molecules, such as [tppzH₂][I₃]₂.2I₂, (II), [tppzH₄][I₃]₂[I]₂, (III), [tppzH₄][Br]₄.2H₂O, (IV), (Padgett et al., 2005), [tppzH₄][Br]₂[Br₄], (V), (Aragoni et al., 2005a), [tppzH₂][ICl₂]₂, (VI), (Aragoni et al., 2005b), [tppzH₄][Cl]₄.2H₂O, (VII), (Graf & Stoeckli-Evans, 1996) and [tppzH₂][B(Ph)₄]₂, (IIX), (Bock et al., 1992), have been synthesized and characterized by single-crystal X-ray diffraction methods. Several proton-transfer systems using AuCl₄ as proton acceptor molecules, such as [EMI][AuCl₄], (IX), [BMI]₂[AuCl₄].2H₂O, (X), (Hasan et al., 1999), [H₂bipy][AuCl₄][Cl], (XI), (Zhang et al., 2006), [H₇O₃][15-crown-5][AuCl₄], (XII), [H₅O₂][benzo-15-crown-5]₂[AuCl₄], (XIII), (Johnson & Steed, 1998), [H₅O₂]₂[12-crown-4]₂[AuCl₄]₂, (XIV), [H₃O][18-crown-6][AuCl₄], (XV), [H₃O][4-nitrobenzo-18-crown-6][AuCl₄], (XVI), (Calleja et al., 2001), [DPpyH][AuCl₄], (XVII), (Yap et al., 1995), [H₂DA18C6][AuCl₄], (XVIII), (Hojjat Kashani et al., 2008), [Me₂Ph₂phenH][AuCl₄], (XIX), (Yıldırım et al., 2009a) and [pz(py)₂H][AuCl₄], (XX), (Yıldırım et al., 2009b) (EMI is 1-ethyl-3-methylimidazolium, BMI is 1-butyl-3-methylimidazolium, H₂bipy is 2,2'-bipyridinium, DPpyH is 2,6-diphenylpyridinium, H₂DA18C6 is 1,10-diazonia-18-crown-6, Me₂Ph₂phenH is 2,9-dimethyl-4,7-diphenyl-1,10-phenanthrolin-1-ium and pz(py)₂H is 2-[3-(2-pyridyl)pyrazin-2-yl]pyridinium) have been synthesized and characterized by single-crystal X-ray diffraction methods. We report herein the synthesis and crystal structure of the title compound, (I).

The asymmetric unit of (I) contains one half-cation and two half-anions (Fig. 1). The Au^III ions, each lies on an inversion center, have a square-planer coordination geometry. The bond lengths and angles in the cation are in good agreement with the corresponding values in (V) and (IIX). The Au—Cl bond lengths (Table 1) and angles are within normal range observed in (XIIX), (XIX) and (XX). In the crystal structure, intermolecular C—H···Cl hydrogen bonds (Table 2), π–π contacts between the pyridine rings (Fig. 2), Cg2···Cg2ⁱ and Cg3···Cg3ⁱⁱ [Cg2 and Cg3 are the centroids of the N2, C3–C7 ring and N3, C8–C12 ring. Symmetry codes: (i) 1-x, -y, 1-z; (ii) 1-x, 1-y, 2-z], with centroid–centroid distances of 3.5548 (16) and 3.7507 (16) Å and Au2···Cg1 contacts (Fig. 2) [Cg1 is the centroid of the N1, C1, C2, N1ⁱⁱⁱ, C1ⁱⁱⁱ, C2ⁱⁱⁱ ring. Symmetry code: (iii) 1-x, 1-y, 1-z] with an Au···centroid distance of 3.6424 (10) Å are effective in the stabilization of the crystal structure, resulting in the formation of a supramolecular structure.

Related literature top

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 top

For the preparation of (I), a solution of 2,3,5,6-tetrakis(2-pyridyl)pyrazine (0.26 g, 0.65 mmol) in CHCl₃ (20 ml) was added to a solution of HAuCl₄.3H₂O, (0.45 g, 1.30 mmol) in methanol (20 ml) and the resulting yellow solution was stirred for 10 min at room temperature. Crystals suitable for X-ray diffraction experiment were obtained by methanol diffusion into a yellow solution in DMF. After one week, yellow prismatic crystals of (I) were isolated (yield: 0.51 g, 73.5%; m. p. 569–570 K).

Structure description top

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).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry codes: (a) -x, 2-y, -z; (b) -x, 1-y, 1-z; (c) 1-x, 1-y, 1-z.]
	Fig. 2. Crystal packing diagram for the title compound. Hydrogen bonds are shown as dashed lines.

2,5-Bis(pyridinium-2-yl)-3,6-bis(2-pyridyl)pyrazine bis[tetrachloridoaurate(III)] top

Crystal data top

(C₂₄H₁₈N₆)[AuCl₄]₂	Z = 1
M_r = 1067.98	F(000) = 498
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0278P)² + 0.1485P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.003
3821 reflections	Δρ_max = 1.76 e Å⁻³
185 parameters	Δρ_min = −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)

Crystal data top

(C₂₄H₁₈N₆)[AuCl₄]₂	γ = 88.8600 (13)°
M_r = 1067.98	V = 721.48 (10) Å³
Triclinic, P1	Z = 1
a = 7.2847 (6) Å	Mo Kα radiation
b = 9.6611 (8) Å	µ = 10.93 mm⁻¹
c = 10.6263 (9) Å	T = 100 K
α = 79.6692 (13)°	0.30 × 0.20 × 0.20 mm
β = 78.7378 (12)°

Data collection top

Bruker APEXII CCD diffractometer	3821 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3395 reflections with I > 2σ(I)
T_min = 0.080, T_max = 0.110	R_int = 0.020
8652 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.019	0 restraints
wR(F²) = 0.050	H-atom parameters constrained
S = 1.05	Δρ_max = 1.76 e Å⁻³
3821 reflections	Δρ_min = −1.36 e Å⁻³
185 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

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

Hydrogen-bond geometry (Å, º) top

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···Cl1^iv	0.95	2.77	3.680 (3)	161
C6—H6A···Cl2^v	0.95	2.77	3.519 (3)	136

Symmetry codes: (i) −x+1, −y+1, −z+1; (iv) −x+1, −y+1, −z; (v) x, y−1, z+1.

Experimental details

Crystal data
Chemical formula	(C₂₄H₁₈N₆)[AuCl₄]₂
M_r	1067.98
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.2847 (6), 9.6611 (8), 10.6263 (9)
α, β, γ (°)	79.6692 (13), 78.7378 (12), 88.8600 (13)
V (Å³)	721.48 (10)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	10.93
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.080, 0.110
No. of measured, independent and observed [I > 2σ(I)] reflections	8652, 3821, 3395
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.019, 0.050, 1.05
No. of reflections	3821
No. of parameters	185
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.76, −1.36

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

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

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z; (iii) x, y−1, z+1.

Acknowledgements

We thank the Graduate Study Councils of the Islamic Azad University, North Tehran Branch, for financial support.

References

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Volume 67| Part 10| October 2011| Pages m1375-m1376

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2,5-Bis(pyridinium-2-yl)-3,6-bis­­(2-pyrid­yl)pyrazine bis­­[tetra­chlorido­aurate(III)]

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

2,5-Bis(pyridinium-2-yl)-3,6-bis(2-pyridyl)pyrazine bis[tetrachloridoaurate(III)]