6,6′-Dimethyl-2,2′-bipyridin-1-ium tetra­chloridoaurate(III)

Zare Dehnavi, M.; Abedi, A.

doi:10.1107/S160053681202853X

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page m981

https://doi.org/10.1107/S160053681202853X

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6,6′-Dimethyl-2,2′-bipyridin-1-ium tetrachloridoaurate(III)

Marzieh Zare Dehnavi ^a and Anita Abedi ^a ^*

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

(Received 11 June 2012; accepted 23 June 2012; online 30 June 2012)

In the anion of the title compound, (C₁₂H₁₃N₂)[AuCl₄], the Au^III atom has a square-planar coordination. In the crystal, intermolecular N—H⋯Cl and C—H⋯Cl hydrogen bonds and π–π contacts between the pyridine rings [centroid–centroid distance = 3.5419 (19) Å] result in the formation of a supramolecular structure.

Related literature

For related structures, see: Abedi et al. (2008 , 2011 ); Amani et al. (2010 ); Calleja et al. (2001 ); Fazaeli et al. (2010 ); Hasan et al. (1999 ); Hojjat Kashani et al. (2008 ); Johnson & Steed (1998 ); Kalateh et al. (2008 ); Safari et al. (2009 ); Yap et al. (1995 ); Yıldırım et al. (2009a ,b ); Zhang et al. (2006 ).

Experimental

Crystal data

(C₁₂H₁₃N₂)[AuCl₄]
M_r = 524.01
Monoclinic, P 2₁ /n
a = 10.8942 (9) Å
b = 11.6784 (10) Å
c = 12.2866 (11) Å
β = 95.772 (5)°
V = 1555.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 10.13 mm⁻¹
T = 100 K
0.20 × 0.15 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.182, T_max = 0.227
12293 measured reflections
4101 independent reflections
3699 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.049
S = 1.00
4101 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.83 e Å⁻³
Δρ_min = −1.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯Cl3ⁱ	0.82	2.80	3.419 (2)	134
C4—H4A⋯Cl2ⁱⁱ	0.95	2.79	3.434 (4)	126
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x, y-1, z-1.

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681202853X/hy2560sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681202853X/hy2560Isup2.hkl

checkCIF report

Comment top

In the recent years, 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 HAuCl₄ as proton acceptor molecule, such as [EMI][AuCl₄], (II), [BMI]₂[AuCl₄].2H₂O, (III), (Hasan et al., 1999), [H₂bipy][AuCl₄]Cl, (IV), (Zhang et al., 2006), [H₇O₃][15-crown-5][AuCl₄], (V), [H₅O₂][benzo-15-crown-5]₂[AuCl₄], (VI), (Johnson & Steed, 1998), [H₅O₂]₂[12-crown-4]₂[AuCl₄]₂, (VII), [H₃O][18-crown-6][AuCl₄], (VIII), [H₃O][4-nitrobenzo-18-crown-6][AuCl₄], (IX), (Calleja et al., 2001), [Ph₂py.H][AuCl₄], (X), (Yap et al., 1995), [H₂DA18C6][AuCl₄], (XI), (Hojjat Kashani et al., 2008), [Me₂Ph₂phen.H][AuCl₄], (XII), (Yıldırım et al., 2009a), [pz(py)₂.H][AuCl₄], (XIII), (Yıldırım et al., 2009b), [Phpy.H][AuCl₄], (XIV), (Amani et al., 2010), [Dafonium][AuCl₄].[dafone], (XV), (Safari et al., 2009), [tppzH₂][AuCl₄]₂, (XVI), (Abedi et al., 2011) and [TBA]₂[AuCl₄][Cl], (XVII), (Fazaeli et al., 2010) (EMI = 1-ethyl-3-methylimidazolium, BMI = 1-butyl-3-methylimidazolium, H₂bipy = 2,2'-bipyridinium, Ph₂py.H = 2,6-diphenylpyridinium, H₂DA18C6 = 1,10-diazonia-18-crown-6, Me₂Ph₂phen.H = 2,9-dimethyl-4,7-diphenyl-1,10-phenanthrolin-1-ium, pz(py)₂.H = 2-[3-(2-pyridyl)pyrazin-2-yl]pyridinium, Phpy.H = 3-phenylpyridinium, Dafonium = 9-oxo-4,5-diazafluoren-4-ium, dafone = 4,5-diazafluoren-9-one, tppzH₂ = 2,5-bis(pyridinium-2-yl)-3,6-bis(2-pyridyl)pyrazine and TBA = tribenzylammonium) 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).

In the anion of the title compound (Fig. 1), the Au^III atom has a square-planar coordination. The Au—Cl bond lengths and angles are within normal range (XII–XVII). In the crystal, intermolecular N—H···Cl and C—H···Cl hydrogen bonds (Table 1) and π–π contacts between the pyridine rings, Cg1···Cg2ⁱ [Cg1 and Cg2 are the centroids of the rings N1/C1–C5 and N2/C7–C11, respectively. Symmetry code: (i) 2-x, -y, -z], with a centroid–centroid distance of 3.5419 (19) Å, are effective in the stabilization of the crystal structure, resulting in the formation of a supramolecular structure.

Related literature top

For related structures, see: Abedi et al. (2008, 2011); Amani et al. (2010); Calleja et al. (2001); Fazaeli et al. (2010); Hasan et al. (1999); Hojjat Kashani et al. (2008); Johnson & Steed (1998); Kalateh et al. (2008); Safari et al. (2009); Yap et al. (1995); Yıldırım et al. (2009a,b); Zhang et al. (2006).

Experimental top

For the preparation of the title compound, a solution of 6,6'-dimethyl-2,2'-bipyridine (0.21 g, 1.11 mmol) in methanol (10 ml) was added to a solution of HAuCl₄.3H₂O, (0.58 g, 1.11 mmol) in acetonitrile (10 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: 0.46 g, 79.1%; m. p. 453 K).

Structure description top

For related structures, see: Abedi et al. (2008, 2011); Amani et al. (2010); Calleja et al. (2001); Fazaeli et al. (2010); Hasan et al. (1999); Hojjat Kashani et al. (2008); Johnson & Steed (1998); Kalateh et al. (2008); Safari et al. (2009); 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: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: XP in 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.
	Fig. 2. Crystal packing diagram for the title compound. Hydrogen bonds are shown as dashed lines.

6,6'-Dimethyl-2,2'-bipyridin-1-ium tetrachloridoaurate(III) top

Crystal data top

(C₁₂H₁₃N₂)[AuCl₄]	F(000) = 984
M_r = 524.01	D_x = 2.238 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1542 reflections
a = 10.8942 (9) Å	θ = 3.0–30.0°
b = 11.6784 (10) Å	µ = 10.13 mm⁻¹
c = 12.2866 (11) Å	T = 100 K
β = 95.772 (5)°	Prism, yellow
V = 1555.3 (2) Å³	0.20 × 0.15 × 0.15 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	4101 independent reflections
Radiation source: fine-focus sealed tube	3699 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
φ and ω scans	θ_max = 29.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −14→14
T_min = 0.182, T_max = 0.227	k = −15→15
12293 measured reflections	l = −16→16

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: mixed
wR(F²) = 0.049	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0228P)² + 0.3281P] where P = (F_o² + 2F_c²)/3
4101 reflections	(Δ/σ)_max = 0.002
174 parameters	Δρ_max = 0.83 e Å⁻³
0 restraints	Δρ_min = −1.15 e Å⁻³

Crystal data top

(C₁₂H₁₃N₂)[AuCl₄]	V = 1555.3 (2) Å³
M_r = 524.01	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.8942 (9) Å	µ = 10.13 mm⁻¹
b = 11.6784 (10) Å	T = 100 K
c = 12.2866 (11) Å	0.20 × 0.15 × 0.15 mm
β = 95.772 (5)°

Data collection top

Bruker APEXII CCD diffractometer	4101 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3699 reflections with I > 2σ(I)
T_min = 0.182, T_max = 0.227	R_int = 0.032
12293 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	0 restraints
wR(F²) = 0.049	H-atom parameters constrained
S = 1.00	Δρ_max = 0.83 e Å⁻³
4101 reflections	Δρ_min = −1.15 e Å⁻³
174 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
Au1	0.910926 (11)	0.846230 (10)	0.536181 (9)	0.00895 (4)
Cl1	1.05716 (8)	0.80777 (8)	0.67847 (7)	0.01993 (18)
Cl2	0.76133 (7)	0.82538 (7)	0.65184 (6)	0.01523 (16)
Cl3	0.76425 (7)	0.88766 (7)	0.39541 (6)	0.01501 (16)
Cl4	1.05950 (7)	0.86081 (7)	0.41815 (7)	0.01552 (16)
N1	0.7935 (2)	0.0942 (2)	0.0534 (2)	0.0096 (5)
N2	0.9773 (2)	0.2313 (2)	0.0264 (2)	0.0102 (5)
H2N	0.9224	0.2323	0.0676	0.012*
C1	0.8500 (3)	0.0735 (3)	−0.0370 (2)	0.0089 (6)
C2	0.6953 (3)	0.0310 (3)	0.0722 (2)	0.0107 (6)
C3	0.6523 (3)	−0.0561 (3)	0.0007 (3)	0.0136 (6)
H3A	0.5832	−0.1010	0.0158	0.016*
C4	0.7107 (3)	−0.0771 (3)	−0.0928 (3)	0.0154 (7)
H4A	0.6818	−0.1361	−0.1422	0.018*
C5	0.8112 (3)	−0.0112 (3)	−0.1130 (3)	0.0131 (6)
H5A	0.8526	−0.0231	−0.1766	0.016*
C6	0.6349 (3)	0.0588 (3)	0.1736 (3)	0.0146 (7)
H6A	0.6978	0.0635	0.2363	0.022*
H6B	0.5754	−0.0013	0.1867	0.022*
H6C	0.5920	0.1325	0.1640	0.022*
C7	0.9564 (3)	0.1483 (3)	−0.0502 (3)	0.0098 (6)
C8	1.0677 (3)	0.3099 (3)	0.0276 (3)	0.0129 (6)
C9	1.1446 (3)	0.3059 (3)	−0.0547 (3)	0.0144 (7)
H9A	1.2088	0.3605	−0.0571	0.017*
C10	1.1274 (3)	0.2212 (3)	−0.1343 (3)	0.0148 (7)
H10A	1.1808	0.2183	−0.1908	0.018*
C11	1.0340 (3)	0.1407 (3)	−0.1328 (3)	0.0124 (6)
H11A	1.0234	0.0822	−0.1867	0.015*
C12	1.0788 (3)	0.3951 (3)	0.1189 (3)	0.0185 (7)
H12A	1.1431	0.4510	0.1067	0.028*
H12B	1.1007	0.3555	0.1885	0.028*
H12C	0.9999	0.4348	0.1215	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Au1	0.00970 (6)	0.00822 (7)	0.00884 (6)	0.00079 (4)	0.00044 (4)	−0.00109 (4)
Cl1	0.0138 (4)	0.0335 (5)	0.0120 (4)	0.0015 (4)	−0.0011 (3)	0.0048 (3)
Cl2	0.0142 (4)	0.0191 (4)	0.0129 (3)	−0.0038 (3)	0.0041 (3)	−0.0045 (3)
Cl3	0.0141 (4)	0.0159 (4)	0.0143 (3)	0.0012 (3)	−0.0021 (3)	0.0022 (3)
Cl4	0.0134 (4)	0.0201 (4)	0.0136 (4)	0.0027 (3)	0.0039 (3)	0.0017 (3)
N1	0.0119 (13)	0.0076 (13)	0.0093 (12)	0.0009 (10)	0.0004 (10)	0.0012 (10)
N2	0.0088 (12)	0.0109 (13)	0.0113 (12)	−0.0010 (10)	0.0022 (10)	−0.0012 (10)
C1	0.0084 (14)	0.0084 (14)	0.0098 (13)	0.0040 (11)	0.0010 (11)	0.0008 (11)
C2	0.0134 (15)	0.0090 (15)	0.0096 (13)	0.0033 (12)	0.0002 (11)	0.0027 (12)
C3	0.0116 (15)	0.0122 (16)	0.0167 (15)	−0.0024 (13)	−0.0002 (12)	0.0004 (13)
C4	0.0167 (16)	0.0137 (16)	0.0153 (15)	−0.0034 (13)	−0.0009 (13)	−0.0062 (13)
C5	0.0175 (16)	0.0119 (16)	0.0099 (14)	0.0000 (13)	0.0022 (12)	−0.0024 (12)
C6	0.0161 (16)	0.0156 (17)	0.0125 (15)	−0.0028 (13)	0.0036 (12)	0.0015 (13)
C7	0.0099 (14)	0.0092 (15)	0.0099 (14)	0.0004 (12)	−0.0013 (11)	0.0001 (12)
C8	0.0138 (15)	0.0088 (15)	0.0157 (15)	−0.0023 (13)	−0.0009 (12)	0.0009 (12)
C9	0.0104 (15)	0.0160 (17)	0.0167 (16)	−0.0015 (13)	0.0004 (13)	0.0040 (13)
C10	0.0125 (15)	0.0185 (17)	0.0137 (15)	0.0027 (13)	0.0027 (12)	0.0033 (13)
C11	0.0143 (15)	0.0129 (16)	0.0098 (14)	0.0010 (13)	−0.0006 (12)	−0.0008 (12)
C12	0.0186 (17)	0.0157 (17)	0.0215 (17)	−0.0050 (14)	0.0032 (14)	−0.0072 (14)

Geometric parameters (Å, º) top

Au1—Cl2	2.2804 (8)	C4—H4A	0.9500
Au1—Cl3	2.2854 (8)	C5—H5A	0.9500
Au1—Cl4	2.2856 (8)	C6—H6A	0.9800
Au1—Cl1	2.2882 (8)	C6—H6B	0.9800
N1—C2	1.339 (4)	C6—H6C	0.9800
N1—C1	1.345 (4)	C7—C11	1.388 (5)
N2—C8	1.345 (4)	C8—C9	1.378 (5)
N2—C7	1.353 (4)	C8—C12	1.496 (5)
N2—H2N	0.8221	C9—C10	1.390 (5)
C1—C5	1.396 (4)	C9—H9A	0.9500
C1—C7	1.474 (4)	C10—C11	1.387 (5)
C2—C3	1.395 (4)	C10—H10A	0.9500
C2—C6	1.502 (4)	C11—H11A	0.9500
C3—C4	1.390 (5)	C12—H12A	0.9800
C3—H3A	0.9500	C12—H12B	0.9800
C4—C5	1.382 (5)	C12—H12C	0.9800

Cl2—Au1—Cl3	90.29 (3)	C2—C6—H6B	109.5
Cl2—Au1—Cl4	178.02 (3)	H6A—C6—H6B	109.5
Cl3—Au1—Cl4	89.42 (3)	C2—C6—H6C	109.5
Cl2—Au1—Cl1	89.38 (3)	H6A—C6—H6C	109.5
Cl3—Au1—Cl1	179.00 (3)	H6B—C6—H6C	109.5
Cl4—Au1—Cl1	90.94 (3)	N2—C7—C11	118.8 (3)
C2—N1—C1	118.9 (3)	N2—C7—C1	115.3 (3)
C8—N2—C7	124.6 (3)	C11—C7—C1	125.8 (3)
C8—N2—H2N	124.1	N2—C8—C9	117.8 (3)
C7—N2—H2N	110.9	N2—C8—C12	117.8 (3)
N1—C1—C5	123.1 (3)	C9—C8—C12	124.3 (3)
N1—C1—C7	114.5 (3)	C8—C9—C10	119.5 (3)
C5—C1—C7	122.4 (3)	C8—C9—H9A	120.3
N1—C2—C3	121.1 (3)	C10—C9—H9A	120.3
N1—C2—C6	116.6 (3)	C11—C10—C9	121.3 (3)
C3—C2—C6	122.2 (3)	C11—C10—H10A	119.3
C4—C3—C2	119.8 (3)	C9—C10—H10A	119.3
C4—C3—H3A	120.1	C10—C11—C7	117.9 (3)
C2—C3—H3A	120.1	C10—C11—H11A	121.1
C5—C4—C3	119.2 (3)	C7—C11—H11A	121.1
C5—C4—H4A	120.4	C8—C12—H12A	109.5
C3—C4—H4A	120.4	C8—C12—H12B	109.5
C4—C5—C1	117.8 (3)	H12A—C12—H12B	109.5
C4—C5—H5A	121.1	C8—C12—H12C	109.5
C1—C5—H5A	121.1	H12A—C12—H12C	109.5
C2—C6—H6A	109.5	H12B—C12—H12C	109.5

C2—N1—C1—C5	0.0 (4)	N1—C1—C7—N2	−3.9 (4)
C2—N1—C1—C7	179.6 (3)	C5—C1—C7—N2	175.6 (3)
C1—N1—C2—C3	0.8 (4)	N1—C1—C7—C11	176.4 (3)
C1—N1—C2—C6	−179.2 (3)	C5—C1—C7—C11	−4.1 (5)
N1—C2—C3—C4	−1.0 (5)	C7—N2—C8—C9	0.0 (5)
C6—C2—C3—C4	179.1 (3)	C7—N2—C8—C12	−179.4 (3)
C2—C3—C4—C5	0.3 (5)	N2—C8—C9—C10	−0.8 (5)
C3—C4—C5—C1	0.6 (5)	C12—C8—C9—C10	178.6 (3)
N1—C1—C5—C4	−0.7 (5)	C8—C9—C10—C11	0.3 (5)
C7—C1—C5—C4	179.7 (3)	C9—C10—C11—C7	1.0 (5)
C8—N2—C7—C11	1.3 (5)	N2—C7—C11—C10	−1.8 (4)
C8—N2—C7—C1	−178.4 (3)	C1—C7—C11—C10	177.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···Cl3ⁱ	0.82	2.80	3.419 (2)	134
C4—H4A···Cl2ⁱⁱ	0.95	2.79	3.434 (4)	126

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x, y−1, z−1.

Experimental details

Crystal data
Chemical formula	(C₁₂H₁₃N₂)[AuCl₄]
M_r	524.01
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	10.8942 (9), 11.6784 (10), 12.2866 (11)
β (°)	95.772 (5)
V (Å³)	1555.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	10.13
Crystal size (mm)	0.20 × 0.15 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.182, 0.227
No. of measured, independent and observed [I > 2σ(I)] reflections	12293, 4101, 3699
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.049, 1.00
No. of reflections	4101
No. of parameters	174
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.83, −1.15

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···Cl3ⁱ	0.82	2.80	3.419 (2)	134
C4—H4A···Cl2ⁱⁱ	0.95	2.79	3.434 (4)	126

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x, y−1, z−1.

Acknowledgements

We thank the Iranian National Science and Research Foundation (grant No. 89002417) and the Islamic Azad University, North Tehran Branch, for financial support.

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