Literature DB >> 21583742

2-[3-(2-Pyrid-yl)pyrazin-2-yl]pyridinium tetra-chloridoaurate(III).

Sema Öztürk Yıldırım, Mehmet Akkurt, Nasser Safari, Vahid Amani, Vickie McKee.   

Abstract

In the anion of the title compound, (C(14)H(11)N(4))[AuCl(4)], the Au(III) atom has an almost perfect square-planar coordination. In the crystal structure, an intra-molecular N-H⋯N and intermolecular C-H⋯Cl hydrogen bonds are observed. In addition, there is also a ring-metal inter-action between the pyrazine ring and the Au(III) atom; the distance between the centroid of the pyrazine ring and the Au(III) atom is 3.628 (2) Å.

Entities:  

Year:  2009        PMID： 21583742      PMCID： PMC2977556          DOI： 10.1107/S1600536809012264

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For proton-transfer systems involving [AuCl4], see: Calleja et al. (2001 ▶); Hasan et al. (1999 ▶); Hojjat Kashani et al. (2008 ▶); Johnson & Steed (1998 ▶); Safari et al. (2009 ▶); Yap et al. (1995 ▶); Zhang et al. (2006 ▶).

Experimental

Crystal data

(C14H11N4)[AuCl4] M = 574.04 Monoclinic, a = 7.4098 (6) Å b = 15.5188 (13) Å c = 14.6197 (12) Å β = 90.380 (1)° V = 1681.1 (2) Å3 Z = 4 Mo Kα radiation μ = 9.39 mm−1 T = 150 K 0.19 × 0.14 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (; Sheldrick, 2003 ▶) T min = 0.238, T max = 0.430 19688 measured reflections 5261 independent reflections 4363 reflections with I > 2σ(I) R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.024 wR(F 2) = 0.052 S = 0.98 5261 reflections 208 parameters H-atom parameters constrained Δρmax = 1.19 e Å−3 Δρmin = −0.59 e Å−3 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 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809012264/is2406sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012264/is2406Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
(C14H11N4)[AuCl4]F(000) = 1080
Mr = 574.04Dx = 2.268 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6388 reflections
a = 7.4098 (6) Åθ = 2.6–30.4°
b = 15.5188 (13) ŵ = 9.39 mm−1
c = 14.6197 (12) ÅT = 150 K
β = 90.380 (1)°Block, yellow
V = 1681.1 (2) Å30.19 × 0.14 × 0.09 mm
Z = 4
Bruker APEXII CCD diffractometer5261 independent reflections
Radiation source: sealed tube4363 reflections with I > 2σ(I)
graphiteRint = 0.034
φ and ω scansθmax = 31.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)h = −10→10
Tmin = 0.238, Tmax = 0.430k = −22→21
19688 measured reflectionsl = −21→20
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.052H-atom parameters constrained
S = 0.98w = 1/[σ2(Fo2) + (0.025P)2], where P = (Fo2 + 2Fc2)/3
5261 reflections(Δ/σ)max = 0.001
208 parametersΔρmax = 1.19 e Å−3
0 restraintsΔρmin = −0.59 e Å−3
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.
xyzUiso*/Ueq
N11.1698 (4)−0.52205 (18)0.12698 (19)0.0357 (8)
N21.1649 (4)−0.54680 (16)0.3126 (2)0.0360 (9)
N31.0216 (3)−0.30683 (16)0.16412 (16)0.0294 (8)
N41.0255 (3)−0.32719 (16)0.33648 (16)0.0282 (7)
C11.2037 (5)−0.5982 (2)0.1627 (3)0.0409 (11)
C21.1997 (5)−0.6103 (2)0.2554 (3)0.0431 (13)
C31.1299 (4)−0.4683 (2)0.2781 (2)0.0296 (9)
C41.1307 (4)−0.45514 (18)0.1822 (2)0.0268 (8)
C51.0952 (4)−0.37680 (19)0.1264 (2)0.0260 (8)
C61.1306 (4)−0.3760 (2)0.0328 (2)0.0334 (9)
C71.0901 (4)−0.3036 (2)−0.0181 (2)0.0392 (10)
C81.0152 (4)−0.2326 (2)0.0230 (2)0.0374 (10)
C90.9807 (4)−0.2366 (2)0.1154 (2)0.0334 (9)
C101.0970 (4)−0.40505 (19)0.3547 (2)0.0280 (8)
C111.1365 (4)−0.4282 (2)0.4450 (2)0.0330 (10)
C121.0989 (4)−0.3714 (2)0.5152 (2)0.0361 (10)
C131.0247 (4)−0.2920 (2)0.4954 (2)0.0355 (10)
C140.9907 (4)−0.2725 (2)0.4046 (2)0.0332 (9)
Au10.88109 (1)0.05497 (1)0.26548 (1)0.0239 (1)
Cl10.97121 (13)0.19452 (5)0.24868 (6)0.0427 (3)
Cl20.86854 (13)0.07321 (6)0.41954 (5)0.0401 (3)
Cl30.78564 (11)−0.08392 (5)0.28205 (5)0.0346 (2)
Cl40.89453 (13)0.03479 (6)0.11117 (5)0.0418 (3)
H11.23080−0.644300.124500.0490*
H21.22220−0.665000.278800.0520*
H30.99980−0.307000.221800.0350*
H61.18110−0.424000.004800.0400*
H71.11370−0.30280−0.080500.0470*
H80.98850−0.18330−0.010600.0450*
H90.92800−0.189600.144300.0400*
H111.18790−0.481600.457800.0400*
H121.12350−0.386700.575500.0430*
H130.99840−0.252800.541600.0430*
H140.94140−0.219000.390400.0400*
U11U22U33U12U13U23
N10.0365 (15)0.0331 (14)0.0375 (15)0.0023 (12)0.0026 (12)−0.0081 (12)
N20.0393 (15)0.0238 (14)0.0446 (17)0.0003 (11)−0.0106 (13)0.0026 (11)
N30.0322 (13)0.0321 (14)0.0240 (12)0.0022 (11)0.0001 (10)0.0000 (10)
N40.0301 (13)0.0277 (13)0.0268 (12)0.0001 (10)0.0003 (10)0.0021 (10)
C10.0405 (19)0.0322 (18)0.050 (2)0.0046 (15)0.0005 (16)−0.0094 (15)
C20.0360 (18)0.0280 (17)0.065 (3)0.0023 (14)−0.0124 (17)−0.0007 (16)
C30.0251 (14)0.0253 (14)0.0384 (18)−0.0014 (11)−0.0038 (12)0.0010 (13)
C40.0231 (14)0.0268 (15)0.0304 (15)−0.0001 (11)0.0011 (11)−0.0020 (12)
C50.0232 (13)0.0288 (15)0.0260 (14)−0.0025 (11)−0.0014 (11)−0.0032 (12)
C60.0336 (16)0.0368 (17)0.0299 (16)0.0024 (13)0.0043 (13)−0.0030 (13)
C70.0327 (17)0.055 (2)0.0298 (16)−0.0009 (15)0.0047 (13)0.0038 (15)
C80.0367 (17)0.0423 (19)0.0333 (17)0.0008 (15)0.0012 (13)0.0121 (14)
C90.0399 (17)0.0312 (16)0.0289 (15)0.0063 (13)−0.0030 (13)0.0006 (12)
C100.0272 (14)0.0268 (15)0.0300 (15)−0.0050 (12)0.0001 (12)0.0030 (12)
C110.0303 (16)0.0327 (17)0.0359 (17)−0.0044 (12)−0.0045 (13)0.0061 (13)
C120.0411 (18)0.0435 (19)0.0236 (15)−0.0077 (15)−0.0049 (13)0.0024 (13)
C130.0385 (17)0.0395 (18)0.0286 (16)−0.0011 (14)−0.0004 (13)−0.0044 (14)
C140.0368 (17)0.0331 (16)0.0296 (16)0.0038 (13)0.0032 (13)0.0025 (13)
Au10.0246 (1)0.0239 (1)0.0232 (1)0.0008 (1)−0.0003 (1)0.0022 (1)
Cl10.0579 (5)0.0295 (4)0.0407 (4)−0.0118 (4)−0.0047 (4)0.0055 (3)
Cl20.0549 (5)0.0410 (4)0.0245 (4)−0.0015 (4)0.0016 (3)−0.0010 (3)
Cl30.0420 (4)0.0243 (3)0.0376 (4)−0.0005 (3)0.0064 (3)0.0020 (3)
Cl40.0535 (5)0.0485 (5)0.0235 (4)−0.0127 (4)0.0017 (3)−0.0010 (3)
Au1—Cl12.2801 (8)C6—C71.380 (4)
Au1—Cl22.2725 (8)C7—C81.374 (4)
Au1—Cl32.2818 (8)C8—C91.378 (4)
Au1—Cl42.2805 (8)C10—C111.397 (4)
N1—C41.348 (4)C11—C121.383 (4)
N1—C11.316 (4)C12—C131.379 (4)
N2—C21.319 (5)C13—C141.383 (4)
N2—C31.343 (4)C1—H10.9300
N3—C91.336 (4)C2—H20.9300
N3—C51.336 (4)C6—H60.9300
N4—C141.335 (4)C7—H70.9300
N4—C101.345 (4)C8—H80.9300
N3—H30.8600C9—H90.9300
C1—C21.369 (6)C11—H110.9300
C3—C101.510 (4)C12—H120.9300
C3—C41.417 (4)C13—H130.9300
C4—C51.487 (4)C14—H140.9300
C5—C61.395 (4)
Cl1···Cl43.2394 (12)C10···N33.222 (4)
Cl1···C2i3.471 (3)C11···Cl4xiv3.497 (3)
Cl1···Cl23.2230 (12)C11···C11ix3.419 (4)
Cl2···Cl33.2167 (12)C11···Cl4xii3.622 (3)
Cl2···Cl13.2230 (12)C12···N2ix3.440 (4)
Cl2···N1ii3.472 (3)C12···C8xiv3.483 (4)
Cl2···C5iii3.582 (3)C12···C9xiv3.592 (4)
Cl3···Cl23.2167 (12)C12···Cl4xiv3.627 (3)
Cl3···Cl43.2113 (11)C13···C7ii3.550 (4)
Cl4···Cl13.2394 (12)C14···C7ii3.395 (4)
Cl4···C11iv3.622 (3)C1···H7x3.0500
Cl4···C12v3.627 (3)C3···H32.8000
Cl4···C11v3.497 (3)C7···H1x2.9500
Cl4···Cl33.2113 (11)C7···H14viii2.9600
Cl1···H2i2.9000C9···H2iv2.9000
Cl1···H7vi3.0400C10···H32.5700
Cl2···H6ii2.9800C12···H8xiv3.0400
Cl2···H13vii3.0100C14···H32.7300
Cl3···H7ii2.9600C14···H1iv2.9000
Cl3···H142.8700C14···H7ii3.0400
Cl3···H92.8100H1···C14xii2.9000
Cl4···H8vi2.8700H1···C7x2.9500
Cl4···H12v3.0900H2···C9xii2.9000
Cl4···H11v2.8300H2···Cl1xi2.9000
N1···N22.741 (4)H3···C32.8000
N1···Cl2viii3.472 (3)H3···C102.5700
N2···C12ix3.440 (4)H3···N41.7100
N2···N12.741 (4)H3···C142.7300
N3···C103.222 (4)H6···N12.3500
N3···N42.540 (3)H6···Cl2viii2.9800
N4···N32.540 (3)H7···Cl1vi3.0400
N4···C53.212 (4)H7···C1x3.0500
N1···H62.3500H7···Cl3viii2.9600
N2···H112.3600H7···C14viii3.0400
N2···H12ix2.8900H7···H14viii2.4900
N4···H31.7100H8···Cl4vi2.8700
C1···C7x3.387 (5)H8···C12v3.0400
C2···Cl1xi3.471 (3)H9···Cl32.8100
C2···C9xii3.600 (5)H11···N22.3600
C5···N43.212 (4)H11···Cl4xiv2.8300
C5···Cl2xiii3.582 (3)H12···Cl4xiv3.0900
C7···C14viii3.395 (4)H12···N2ix2.8900
C7···C1x3.387 (5)H13···Cl2vii3.0100
C7···C13viii3.550 (4)H14···H7ii2.4900
C8···C12v3.483 (4)H14···Cl32.8700
C9···C2iv3.600 (5)H14···C7ii2.9600
C9···C12v3.592 (4)
Cl3—Au1—Cl489.48 (3)C3—C10—C11120.0 (3)
Cl1—Au1—Cl490.52 (3)N4—C10—C3120.2 (3)
Cl1—Au1—Cl290.14 (3)N4—C10—C11119.9 (3)
Cl1—Au1—Cl3178.97 (3)C10—C11—C12119.7 (3)
Cl2—Au1—Cl389.87 (3)C11—C12—C13119.7 (3)
Cl2—Au1—Cl4179.25 (3)C12—C13—C14117.8 (3)
C1—N1—C4119.7 (3)N4—C14—C13122.8 (3)
C2—N2—C3118.5 (3)N1—C1—H1120.00
C5—N3—C9122.3 (3)C2—C1—H1120.00
C10—N4—C14120.1 (2)C1—C2—H2119.00
C9—N3—H3119.00N2—C2—H2119.00
C5—N3—H3119.00C5—C6—H6120.00
N1—C1—C2120.7 (3)C7—C6—H6120.00
N2—C2—C1122.1 (3)C6—C7—H7120.00
C4—C3—C10129.9 (3)C8—C7—H7120.00
N2—C3—C4120.0 (3)C9—C8—H8121.00
N2—C3—C10110.1 (3)C7—C8—H8121.00
N1—C4—C5109.8 (3)N3—C9—H9119.00
N1—C4—C3118.9 (3)C8—C9—H9119.00
C3—C4—C5131.2 (3)C10—C11—H11120.00
C4—C5—C6120.8 (3)C12—C11—H11120.00
N3—C5—C6118.5 (3)C13—C12—H12120.00
N3—C5—C4120.6 (3)C11—C12—H12120.00
C5—C6—C7119.7 (3)C12—C13—H13121.00
C6—C7—C8120.3 (3)C14—C13—H13121.00
C7—C8—C9118.1 (3)C13—C14—H14119.00
N3—C9—C8121.1 (3)N4—C14—H14119.00
C4—N1—C1—C20.0 (5)N2—C3—C10—C1111.3 (4)
C1—N1—C4—C31.0 (5)C4—C3—C10—N414.0 (5)
C1—N1—C4—C5−179.2 (3)C4—C3—C10—C11−167.7 (3)
C3—N2—C2—C11.0 (5)N1—C4—C5—N3167.6 (3)
C2—N2—C3—C40.1 (5)N1—C4—C5—C6−9.6 (4)
C2—N2—C3—C10−179.1 (3)C3—C4—C5—N3−12.7 (5)
C9—N3—C5—C4−177.1 (3)C3—C4—C5—C6170.2 (3)
C9—N3—C5—C60.1 (4)N3—C5—C6—C70.3 (4)
C5—N3—C9—C8−0.9 (4)C4—C5—C6—C7177.6 (3)
C14—N4—C10—C3177.7 (3)C5—C6—C7—C80.0 (4)
C14—N4—C10—C11−0.7 (4)C6—C7—C8—C9−0.7 (4)
C10—N4—C14—C13−0.1 (4)C7—C8—C9—N31.1 (4)
N1—C1—C2—N2−1.1 (6)N4—C10—C11—C121.1 (4)
N2—C3—C4—N1−1.1 (4)C3—C10—C11—C12−177.3 (3)
N2—C3—C4—C5179.2 (3)C10—C11—C12—C13−0.8 (4)
C10—C3—C4—N1177.9 (3)C11—C12—C13—C140.0 (4)
C10—C3—C4—C5−1.9 (5)C12—C13—C14—N40.5 (5)
N2—C3—C10—N4−167.1 (3)
D—H···AD—HH···AD···AD—H···A
N3—H3···N40.861.712.540 (3)160
C6—H6···N10.932.352.667 (4)100
C9—H9···Cl30.932.813.699 (3)161
C11—H11···N20.932.362.680 (4)100
C11—H11···Cl4xiv0.932.833.497 (3)130
Au1—Cl12.2801 (8)
Au1—Cl22.2725 (8)
Au1—Cl32.2818 (8)
Au1—Cl42.2805 (8)
Cl3—Au1—Cl489.48 (3)
Cl1—Au1—Cl490.52 (3)
Cl1—Au1—Cl290.14 (3)
Cl1—Au1—Cl3178.97 (3)
Cl2—Au1—Cl389.87 (3)
Cl2—Au1—Cl4179.25 (3)
Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N3—H3⋯N40.861.712.540 (3)160
C9—H9⋯Cl30.932.813.699 (3)161
C11—H11⋯Cl4i0.932.833.497 (3)130

Symmetry code: (i) .

  4 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Oxonium ions from aqua regia: isolation by hydrogen bonding to crown ethers.

Authors:  M Calleja; K Johnson; W J Belcher; J W Steed
Journal:  Inorg Chem       Date:  2001-09-10       Impact factor: 5.165

3.  1,4,10,13-Tetra-oxa-7,16-diazo-niacyclo-octadecane bis-[tetra-chloridoaurate(III)] dihydrate.

Authors:  Leila Hojjat Kashani; Mohammad Yousefi; Vahid Amani; Hamid Reza Khavasi
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-05-24

4.  9-Oxo-4,5-diaza-fluoren-4-ium tetra-chloridoaurate(III)-4,5-diaza-fluoren-9-one (1/1).

Authors:  Nasser Safari; Vahid Amani; Behrouz Notash; Seik Weng Ng
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-02-28
  4 in total
  4 in total

1.  Bis(tribenzyl-ammonium) tetra-chloridoaurate(III) chloride.

Authors:  Yousef Fazaeli; Vahid Amani; Mostafa M Amini; Hamid Reza Khavasi
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-01-30

2.  3-Phenyl-pyridinium tetra-chlorido-aurate(III).

Authors:  Vahid Amani; Nasser Safari; Hamid Reza Khavasi
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-02-27

3.  6,6'-Dimethyl-2,2'-bipyridin-1-ium tetra-chloridoaurate(III).

Authors:  Marzieh Zare Dehnavi; Anita Abedi
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-06-30

4.  2,5-Bis(pyridinium-2-yl)-3,6-bis-(2-pyrid-yl)pyrazine bis-[tetra-chlorido-aurate(III)].

Authors:  Anita Abedi; Azra Dabbaghi; Vahid Amani
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-09-14
  4 in total

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