2,9-Dimethyl-4,7-diphenyl-1,10-phenanthrolin-1-ium tetra­chloridoaurate(III)

Yıldırım, S.Ö.; Akkurt, M.; Safari, N.; Abedi, A.; Amani, V.; McKee, V.

doi:10.1107/S1600536809011994

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Pages m479-m480

doi:10.1107/S1600536809011994

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2,9-Dimethyl-4,7-diphenyl-1,10-phenanthrolin-1-ium tetrachloridoaurate(III)

Sema Öztürk Yıldırım,^a Mehmet Akkurt,^a ^* Nasser Safari,^b Anita Abedi,^c Vahid Amani ^b and Vickie McKee ^d

^aDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bDepartment of Chemistry, Shahid Beheshti University, GC, Evin, Tehran 1983963113, Iran, ^cDepartment of Chemistry, North Tehran Branch, Islamic Azad University, Tehran, Iran, and ^dChemistry Department, Loughborough University, Loughborough, Leicestershire LE11 3TU, England
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 30 March 2009; accepted 31 March 2009; online 2 April 2009)

Both the cation and anion of the title compound, (C₂₆H₂₁N₂)[AuCl₄], are disposed about a plane of mirror symmetry. The 2,9-dimethyl-4,7-diphenyl-1,10-phenanthrolinium ring is oriented at a dihedral angle of 44.2 (1)° with respect to the planar phenyl ring systems. The Au^III atom has a square-planar environment defined by four Cl atoms. The crystal structure is stabilized by C—H⋯π and Au⋯π ring–metal (3.551 Å) interactions. In the crystal structure, the molecules stack along the c axis via N—H⋯N hydrogen-bond interactions.

Related literature

For general background to proton-transfer systems and their structures, see: Abedi et al. (2008 ); Amani et al. (2008 ); Calleja et al. (2001 ); Hasan et al. (1999 ); Hojjat Kashani et al. (2008 ); Johnson & Steed (1998 ); Karaca et al. (2009 ); Yap et al. (1995 ); Zhang et al. (2006 ).

Experimental

Crystal data

(C₂₆H₂₁N₂)[AuCl₄]
M_r = 700.22
Orthorhombic, P n m a
a = 13.5195 (10) Å
b = 22.9565 (17) Å
c = 7.5556 (6) Å
V = 2345.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 6.75 mm⁻¹
T = 150 K
0.20 × 0.06 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.345, T_max = 0.774
24337 measured reflections
3265 independent reflections
2835 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.054
S = 1.03
3265 reflections
159 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.85 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯N1ⁱ	0.76 (5)	2.28 (5)	2.646 (3)	111 (4)
C1—H1B⋯Cg3ⁱⁱ	0.96	2.76	3.574 (3)	143
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z]$ ; (ii) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ . Cg3 is the centroid of the C8–C13 ring.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809011994/hg2496sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809011994/hg2496Isup2.hkl

checkCIF report

Comment top

In recent years, there has been considerable interest in proton transfer systems and their structures (Amani et al., 2008; Abedi et al., 2008; Karaca et al., 2009). Several proton transfer systems using HAuCl₄ with proton acceptor molecules, such as [EMI][AuCl₄] and [BMI]₂[AuCl₄].2H₂O (Hasan et al., 1999), [H₂bipy][AuCl₄][Cl] (Zhang et al., 2006), [H₇O₃][15-crown-5][AuCl₄] and [H₅O₂][benzo-15-crown-5]₂[AuCl₄] (Johnson & Steed, 1998), [H₅O₂]₂[12-crown-4]₂[AuCl₄]_2, [H₃O][18-crown-6][AuCl₄] and [H₃O][4-nitrobenzo-18-crown-6][AuCl₄] (Calleja et al., 2001), [DPpy.H][AuCl₄] (Yap et al., 1995) and [H₂DA18C6][AuCl₄].2H₂O (Hojjat Kashani et al., 2008) [where EMI is 1-ethyl-3-methylimidazolium,BMI is 1-butyl-3-methylimidazolium, H₂bipy is 2, 2'-bipyridinium, DPpy.H is 2,6-diphenylpyridinium and H₂DA18C6 is 1,10-diazonia-18-crown-6] 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).

Both the cation and anion of the title compound (Fig. 1) are disposed about a plane of mirror symmetry. The 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline ring is oriented at a dihedral angle of 44.2 (1)° with respect to the planar phenyl ring systems. The Au ion has a square-planar environment defined by four Cl atoms. In AuCl₄ anion, the Au—Cl bond lengths and Cl—Au—Cl bond angles are normal ranges. In the crystal structure, there exist ring-metal interactions [Cg2···Au1(x, y, z) = 3.551 Å and Cg2···Au1(x, 1/2 - y, z) = 3.551 Å, where Cg2 is a centroid of the central benzene ring (C5–C7/C5b–C7b) of the cation molecule]. For C1—H1B···Cg3 interaction, C1···Cg3 = 3.574Å, where Cg3 is a centroid of the phenyl ring (C8 –C13) (Table 2). View of the packing of (I) down the c-axis is given in Fig. 2.

Related literature top

For general background to proton-transfer systems and their structures, see: Abedi et al. (2008); Amani et al. (2008); Calleja et al. (2001); Hasan et al. (1999); Hojjat Kashani, Yousefi, Amani & Khavasi (2008); Johnson & Steed (1998); Karaca et al. (2009); Yap et al. (1995); Zhang et al. (2006). Cg3 is the centroid of the C8–C13 ring.

Experimental top

For the preparation of the title compound, a solution of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (0.15 g, 0.44 mmol) in HCCl₃ (10 ml) was added to a solution of HAuCl₄.3H₂O, (0.17 g, 0.44 mmol) in ethanol (5 ml) and the resulting yellow solution was stirred for 15 min at 313 K. This solution was left to evaporate slowly at room temperature. After one week, yellow prismatic crystals of the title compound were isolated [yield; 0.23 g; 72.1%; m. p. 495 K].

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. ORTEP drawing of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level [Symmetry codes: (a and b) x, 1/2 - y, z].
	Fig. 2. The packing of the title compound viewed down c axis.

2,9-Dimethyl-4,7-diphenyl-1,10-phenanthrolin-1-ium tetrachloridoaurate(III) top

Crystal data top

(C₂₆H₂₁N₂)[AuCl₄]	F(000) = 1352
M_r = 700.22	D_x = 1.983 Mg m⁻³
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ac 2n	Cell parameters from 5918 reflections
a = 13.5195 (10) Å	θ = 2.8–27.6°
b = 22.9565 (17) Å	µ = 6.75 mm⁻¹
c = 7.5556 (6) Å	T = 150 K
V = 2345.0 (3) Å³	Prism, yellow
Z = 4	0.20 × 0.06 × 0.04 mm

Data collection top

Bruker APEXII CCD diffractometer	3265 independent reflections
Radiation source: sealed tube	2835 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
ϕ and ω scans	θ_max = 29.2°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −18→18
T_min = 0.345, T_max = 0.774	k = −31→31
24337 measured reflections	l = −10→10

Refinement top

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.054	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.026P)² + 1.1102P] where P = (F_o² + 2F_c²)/3
3265 reflections	(Δ/σ)_max = 0.001
159 parameters	Δρ_max = 0.85 e Å⁻³
0 restraints	Δρ_min = −0.60 e Å⁻³

Crystal data top

(C₂₆H₂₁N₂)[AuCl₄]	V = 2345.0 (3) Å³
M_r = 700.22	Z = 4
Orthorhombic, Pnma	Mo Kα radiation
a = 13.5195 (10) Å	µ = 6.75 mm⁻¹
b = 22.9565 (17) Å	T = 150 K
c = 7.5556 (6) Å	0.20 × 0.06 × 0.04 mm

Data collection top

Bruker APEXII CCD diffractometer	3265 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2835 reflections with I > 2σ(I)
T_min = 0.345, T_max = 0.774	R_int = 0.046
24337 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	0 restraints
wR(F²) = 0.054	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.85 e Å⁻³
3265 reflections	Δρ_min = −0.60 e Å⁻³
159 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	0.51546 (16)	0.19238 (10)	0.0058 (3)	0.0203 (7)
C1	0.61127 (19)	0.10789 (13)	−0.0819 (4)	0.0271 (8)
C2	0.52022 (19)	0.13465 (11)	−0.0049 (3)	0.0202 (8)
C3	0.4389 (2)	0.10119 (12)	0.0488 (4)	0.0219 (8)
C4	0.3533 (2)	0.12606 (12)	0.1132 (3)	0.0200 (7)
C5	0.35028 (19)	0.18757 (11)	0.1303 (3)	0.0181 (7)
C6	0.43300 (19)	0.21879 (11)	0.0701 (3)	0.0190 (7)
C7	0.27048 (18)	0.22031 (10)	0.2068 (3)	0.0182 (7)
C8	0.26628 (19)	0.08820 (11)	0.1485 (3)	0.0199 (7)
C9	0.2791 (2)	0.03400 (11)	0.2301 (4)	0.0237 (8)
C10	0.2004 (2)	−0.00427 (12)	0.2445 (4)	0.0272 (8)
C11	0.1082 (2)	0.01067 (13)	0.1803 (4)	0.0279 (8)
C12	0.0937 (2)	0.06484 (13)	0.1013 (4)	0.0263 (8)
C13	0.1724 (2)	0.10337 (12)	0.0840 (3)	0.0230 (8)
Au1	0.38322 (1)	0.25000	0.60223 (2)	0.0219 (1)
Cl1	0.53754 (7)	0.25000	0.48086 (15)	0.0343 (3)
Cl2	0.38270 (5)	0.15042 (4)	0.60263 (10)	0.0336 (2)
Cl3	0.22961 (7)	0.25000	0.72842 (14)	0.0298 (3)
HN1	0.556 (4)	0.212 (2)	−0.029 (7)	0.009 (14)*	0.500
H1A	0.59680	0.09310	−0.19790	0.0410*
H1B	0.63310	0.07660	−0.00740	0.0410*
H1C	0.66240	0.13680	−0.08990	0.0410*
H3	0.44280	0.06080	0.04060	0.0260*
H7	0.21760	0.20050	0.25760	0.0220*
H9	0.34070	0.02370	0.27490	0.0280*
H10	0.20980	−0.04040	0.29790	0.0330*
H11	0.05590	−0.01540	0.18980	0.0340*
H12	0.03130	0.07520	0.06010	0.0310*
H13	0.16280	0.13930	0.02960	0.0280*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0164 (11)	0.0215 (11)	0.0230 (12)	−0.0001 (9)	0.0006 (9)	0.0006 (9)
C1	0.0232 (14)	0.0249 (14)	0.0333 (16)	0.0047 (11)	0.0024 (12)	−0.0025 (12)
C2	0.0215 (13)	0.0200 (13)	0.0191 (13)	0.0039 (10)	−0.0020 (10)	−0.0022 (10)
C3	0.0242 (14)	0.0194 (13)	0.0220 (13)	0.0028 (10)	−0.0005 (10)	−0.0008 (10)
C4	0.0204 (12)	0.0205 (12)	0.0192 (12)	−0.0002 (10)	−0.0012 (10)	0.0019 (10)
C5	0.0176 (11)	0.0199 (12)	0.0167 (12)	0.0000 (10)	−0.0030 (9)	0.0014 (9)
C6	0.0186 (12)	0.0205 (13)	0.0180 (12)	0.0000 (10)	−0.0032 (9)	0.0014 (10)
C7	0.0174 (11)	0.0204 (12)	0.0168 (12)	−0.0035 (9)	0.0008 (9)	−0.0002 (10)
C8	0.0207 (12)	0.0198 (12)	0.0193 (12)	−0.0009 (10)	0.0004 (10)	−0.0022 (10)
C9	0.0226 (12)	0.0229 (13)	0.0256 (14)	0.0033 (10)	0.0005 (11)	0.0017 (11)
C10	0.0325 (15)	0.0208 (13)	0.0284 (15)	0.0018 (11)	0.0057 (12)	0.0040 (11)
C11	0.0292 (14)	0.0266 (14)	0.0280 (15)	−0.0071 (12)	0.0058 (12)	−0.0028 (12)
C12	0.0218 (13)	0.0292 (15)	0.0278 (14)	0.0010 (11)	−0.0015 (11)	−0.0031 (12)
C13	0.0246 (14)	0.0210 (13)	0.0233 (13)	0.0025 (10)	−0.0018 (11)	−0.0004 (10)
Au1	0.0177 (1)	0.0292 (1)	0.0187 (1)	0.0000	−0.0022 (1)	0.0000
Cl1	0.0186 (4)	0.0474 (6)	0.0370 (6)	0.0000	0.0020 (4)	0.0000
Cl2	0.0326 (4)	0.0297 (4)	0.0386 (4)	0.0049 (3)	0.0006 (3)	0.0074 (3)
Cl3	0.0212 (4)	0.0383 (6)	0.0298 (5)	0.0000	0.0043 (4)	0.0000

Geometric parameters (Å, º) top

Au1—Cl2ⁱ	2.2860 (9)	C8—C13	1.404 (4)
Au1—Cl3	2.2852 (10)	C8—C9	1.399 (4)
Au1—Cl1	2.2790 (10)	C9—C10	1.384 (4)
Au1—Cl2	2.2860 (9)	C10—C11	1.381 (4)
N1—C2	1.329 (3)	C11—C12	1.393 (4)
N1—C6	1.359 (3)	C12—C13	1.390 (4)
N1—HN1	0.76 (5)	C1—H1B	0.9600
C1—C2	1.494 (4)	C1—H1C	0.9600
C2—C3	1.401 (4)	C1—H1A	0.9600
C3—C4	1.379 (4)	C3—H3	0.9300
C4—C5	1.419 (4)	C7—H7	0.9300
C4—C8	1.487 (4)	C9—H9	0.9300
C5—C6	1.404 (4)	C10—H10	0.9300
C5—C7	1.436 (3)	C11—H11	0.9300
C6—C6ⁱ	1.433 (4)	C12—H12	0.9300
C7—C7ⁱ	1.363 (3)	C13—H13	0.9300

Au1···C7ⁱ	3.423 (2)	C13···C7	3.135 (4)
Au1···C7	3.423 (2)	C3···H10^xii	3.1000
Cl1···Cl3ⁱⁱ	3.4011 (15)	C3···H9	2.8000
Cl1···C7ⁱⁱⁱ	3.520 (3)	C5···H13	2.8700
Cl1···Cl2	3.2333 (11)	C7···H13	2.7100
Cl1···C6	3.485 (3)	C8···H10^xii	2.8900
Cl1···Cl3^iv	3.4011 (15)	C8···H7	2.7900
Cl1···C7^v	3.520 (3)	C9···H3	2.7100
Cl1···Cl2ⁱ	3.2333 (11)	C9···H1B^ix	3.0400
Cl1···C6ⁱ	3.485 (3)	C10···H1B^ix	2.8700
Cl2···Cl1	3.2333 (11)	C11···H1B^ix	2.9200
Cl2···C3^vi	3.636 (3)	C13···H10^xii	3.0500
Cl2···Cl3	3.2269 (11)	C13···H7	2.6600
Cl2···C2^vi	3.519 (2)	HN1···Cl3ⁱⁱⁱ	2.92 (5)
Cl3···Cl1^vii	3.4011 (15)	HN1···H1C	2.2900
Cl3···Cl2	3.2269 (11)	HN1···Cl3^v	2.92 (5)
Cl3···Cl1^viii	3.4011 (15)	HN1···N1ⁱ	2.28 (5)
Cl3···Cl2ⁱ	3.2269 (11)	H1B···C11ⁱⁱⁱ	2.9200
Cl1···H13^v	3.0500	H1B···C10ⁱⁱⁱ	2.8700
Cl1···H13ⁱⁱⁱ	3.0500	H1B···C9ⁱⁱⁱ	3.0400
Cl2···H12ⁱⁱⁱ	2.9200	H1C···HN1	2.2900
Cl2···H1C^ix	3.0000	H1C···Cl3^v	2.9500
Cl3···HN1^x	2.92 (5)	H1C···Cl2ⁱⁱⁱ	3.0000
Cl3···HN1^ix	2.92 (5)	H1C···Cl3ⁱⁱⁱ	2.9500
Cl3···H1C^x	2.9500	H3···H9	2.4000
Cl3···H1C^ix	2.9500	H3···C9	2.7100
N1···N1ⁱ	2.646 (3)	H7···C13	2.6600
N1···HN1ⁱ	2.28 (5)	H7···C8	2.7900
C2···C12ⁱⁱⁱ	3.585 (4)	H7···H13	2.3400
C2···Cl2^xi	3.519 (2)	H9···H3	2.4000
C3···C12ⁱⁱⁱ	3.474 (4)	H9···C3	2.8000
C3···Cl2^xi	3.636 (3)	H10···C13^xiii	3.0500
C6···Cl1	3.485 (3)	H10···C3^xiii	3.1000
C6···Cl1	3.485 (3)	H10···C8^xiii	2.8900
C7···C13	3.135 (4)	H12···Cl2^ix	2.9200
C7···Au1	3.423 (2)	H13···C7	2.7100
C7···Au1	3.423 (2)	H13···H7	2.3400
C7···Cl1^ix	3.520 (3)	H13···Cl1^x	3.0500
C7···Cl1^x	3.520 (3)	H13···Cl1^ix	3.0500
C12···C3^ix	3.474 (4)	H13···C5	2.8700
C12···C2^ix	3.585 (4)

Cl1—Au1—Cl3	179.07 (4)	C8—C9—C10	120.3 (3)
Cl1—Au1—Cl2ⁱ	90.19 (2)	C9—C10—C11	120.6 (3)
Cl2—Au1—Cl3	89.81 (2)	C10—C11—C12	120.0 (3)
Cl2—Au1—Cl2ⁱ	179.62 (3)	C11—C12—C13	120.0 (3)
Cl2ⁱ—Au1—Cl3	89.81 (2)	C8—C13—C12	120.1 (2)
Cl1—Au1—Cl2	90.19 (2)	H1A—C1—H1C	109.00
C2—N1—C6	120.4 (2)	C2—C1—H1A	109.00
C6—N1—HN1	117 (4)	C2—C1—H1B	109.00
C2—N1—HN1	123 (4)	C2—C1—H1C	109.00
C1—C2—C3	122.3 (2)	H1A—C1—H1B	109.00
N1—C2—C3	119.4 (2)	H1B—C1—H1C	109.00
N1—C2—C1	118.3 (2)	C2—C3—H3	119.00
C2—C3—C4	122.3 (3)	C4—C3—H3	119.00
C3—C4—C8	119.0 (2)	C7ⁱ—C7—H7	119.00
C5—C4—C8	122.9 (2)	C5—C7—H7	119.00
C3—C4—C5	117.9 (2)	C8—C9—H9	120.00
C6—C5—C7	117.5 (2)	C10—C9—H9	120.00
C4—C5—C7	125.4 (2)	C9—C10—H10	120.00
C4—C5—C6	117.1 (2)	C11—C10—H10	120.00
C5—C6—C6ⁱ	120.7 (2)	C12—C11—H11	120.00
N1—C6—C6ⁱ	116.5 (2)	C10—C11—H11	120.00
N1—C6—C5	122.8 (2)	C11—C12—H12	120.00
C5—C7—C7ⁱ	121.6 (2)	C13—C12—H12	120.00
C4—C8—C13	120.6 (2)	C12—C13—H13	120.00
C9—C8—C13	119.1 (2)	C8—C13—H13	120.00
C4—C8—C9	120.1 (2)

C6—N1—C2—C1	178.1 (2)	C7—C5—C6—N1	175.7 (2)
C6—N1—C2—C3	0.8 (4)	C7—C5—C6—C6ⁱ	−5.8 (3)
C2—N1—C6—C5	1.0 (4)	C4—C5—C7—C7ⁱ	−175.3 (2)
C2—N1—C6—C6ⁱ	−177.6 (2)	C6—C5—C7—C7ⁱ	5.9 (3)
N1—C2—C3—C4	−0.1 (4)	N1—C6—C6ⁱ—N1ⁱ	0.0 (3)
C1—C2—C3—C4	−177.3 (3)	N1—C6—C6ⁱ—C5ⁱ	178.6 (2)
C2—C3—C4—C5	−2.2 (4)	C5—C6—C6ⁱ—N1ⁱ	−178.6 (2)
C2—C3—C4—C8	173.2 (2)	C5—C6—C6ⁱ—C5ⁱ	0.0 (4)
C3—C4—C5—C6	3.7 (3)	C5—C7—C7ⁱ—C5ⁱ	0.0 (4)
C3—C4—C5—C7	−175.1 (2)	C4—C8—C9—C10	−172.4 (2)
C8—C4—C5—C6	−171.5 (2)	C13—C8—C9—C10	0.9 (4)
C8—C4—C5—C7	9.6 (4)	C4—C8—C13—C12	173.2 (2)
C3—C4—C8—C9	42.3 (3)	C9—C8—C13—C12	−0.1 (4)
C3—C4—C8—C13	−130.8 (3)	C8—C9—C10—C11	−0.6 (4)
C5—C4—C8—C9	−142.5 (3)	C9—C10—C11—C12	−0.4 (5)
C5—C4—C8—C13	44.4 (3)	C10—C11—C12—C13	1.3 (4)
C4—C5—C6—N1	−3.2 (3)	C11—C12—C13—C8	−1.0 (4)
C4—C5—C6—C6ⁱ	175.3 (2)

Symmetry codes: (i) x, −y+1/2, z; (ii) x+1/2, y, −z+3/2; (iii) x+1/2, y, −z+1/2; (iv) x+1/2, −y+1/2, −z+3/2; (v) x+1/2, −y+1/2, −z+1/2; (vi) x, y, z+1; (vii) x−1/2, y, −z+3/2; (viii) x−1/2, −y+1/2, −z+3/2; (ix) x−1/2, y, −z+1/2; (x) x−1/2, −y+1/2, −z+1/2; (xi) x, y, z−1; (xii) −x+1/2, −y, z−1/2; (xiii) −x+1/2, −y, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···N1ⁱ	0.76 (5)	2.28 (5)	2.646 (3)	111 (4)
C1—H1B···Cg3ⁱⁱⁱ	0.96	2.76	3.574 (3)	143

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

Experimental details

Crystal data
Chemical formula	(C₂₆H₂₁N₂)[AuCl₄]
M_r	700.22
Crystal system, space group	Orthorhombic, Pnma
Temperature (K)	150
a, b, c (Å)	13.5195 (10), 22.9565 (17), 7.5556 (6)
V (Å³)	2345.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	6.75
Crystal size (mm)	0.20 × 0.06 × 0.04

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.345, 0.774
No. of measured, independent and observed [I > 2σ(I)] reflections	24337, 3265, 2835
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.687

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.054, 1.03
No. of reflections	3265
No. of parameters	159
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.85, −0.60

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···N1ⁱ	0.76 (5)	2.28 (5)	2.646 (3)	111 (4)
C1—H1B···Cg3ⁱⁱ	0.96	2.76	3.574 (3)	143

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

Acknowledgements

NS and VA are grateful to Shahid Beheshti University for financial support.

References

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