Literature DB >> 22259349

Bis[5-(pyridin-2-yl)pyrazine-2-carbo-nitrile-κN,N]silver hexa-fluorido-phosphate.

Zi Jia Wang1.   

Abstract

In the mononuclear title complex, [Ag(C(10)H(6)N(4))(2)]PF(6), two κ(2)N,N'-chelating 5-(pyridin-2-yl)pyrazine-2-carbonitrile ligands surround the Ag(I) atom, forming a distorted N(4) tetra-hedral coordination geometry. The mononuclear units are inter-connected through π-π inter-actions [centroid-centroid distances = 3.801 (2) and 3.979 (3) Å] and the hexa-fluoridophosphate anions are embedded within the inter-stices. C N⋯π inter-actions [N⋯centroid = 3.519 (2) Å] and C-H.⋯N hydrogen-bonding inter-actions also occur.

Entities:  

Year:  2011        PMID: 22259349      PMCID: PMC3254278          DOI: 10.1107/S1600536811051403

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


Related literature

For coordination complexes with pyridyl-based ligands, see: Boudalis et al. (2003 ▶); Dunne et al. (1997 ▶); Huang et al. (2007 ▶); Wang et al. (2009 ▶). For a related complex with 5-(2-pyrid­yl)pyrazine-2-carbonitrile, see: Wang et al. (2010 ▶).

Experimental

Crystal data

[Ag(C10H6N4)2]PF6 M = 617.22 Triclinic, a = 8.8989 (9) Å b = 9.1711 (10) Å c = 14.0804 (15) Å α = 77.023 (2)° β = 86.926 (2)° γ = 84.809 (2)° V = 1114.5 (2) Å3 Z = 2 Mo Kα radiation μ = 1.05 mm−1 T = 293 K 0.38 × 0.30 × 0.30 mm

Data collection

Bruker APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.861, T max = 1.000 8106 measured reflections 5438 independent reflections 4544 reflections with I > 2σ(I) R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.032 wR(F 2) = 0.090 S = 1.04 5438 reflections 325 parameters H-atom parameters constrained Δρmax = 0.71 e Å−3 Δρmin = −0.37 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 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811051403/bt5734sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051403/bt5734Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Ag(C10H6N4)2]PF6Z = 2
Mr = 617.22F(000) = 608
Triclinic, P1Dx = 1.839 Mg m3
a = 8.8989 (9) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.1711 (10) ÅCell parameters from 252 reflections
c = 14.0804 (15) Åθ = 2.3–28.3°
α = 77.023 (2)°µ = 1.05 mm1
β = 86.926 (2)°T = 293 K
γ = 84.809 (2)°Block, colorless
V = 1114.5 (2) Å30.38 × 0.30 × 0.30 mm
Bruker APEXII CCD area-detector diffractometer5438 independent reflections
Radiation source: fine-focus sealed tube4544 reflections with I > 2σ(I)
graphiteRint = 0.017
ω scansθmax = 28.3°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2007)h = −11→11
Tmin = 0.861, Tmax = 1.000k = −12→11
8106 measured reflectionsl = −14→18
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0427P)2 + 0.4779P] P = (Fo2 + 2Fc2)/3
5438 reflections(Δ/σ)max = 0.001
325 parametersΔρmax = 0.71 e Å3
0 restraintsΔρmin = −0.37 e Å3
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.
xyzUiso*/Ueq
Ag10.48500 (2)0.72149 (2)0.719902 (13)0.05876 (9)
N10.5186 (2)0.8140 (2)0.85560 (14)0.0472 (4)
N20.2770 (2)0.6575 (2)0.83133 (14)0.0488 (4)
N30.0214 (2)0.6780 (2)0.95255 (15)0.0519 (5)
N40.6022 (2)0.6137 (2)0.60099 (14)0.0421 (4)
N50.3774 (2)0.8372 (2)0.55962 (13)0.0417 (4)
N60.3283 (2)0.9988 (2)0.37004 (15)0.0512 (5)
N7−0.2337 (3)0.5344 (3)0.8368 (2)0.0701 (7)
N80.0293 (3)1.2382 (3)0.4069 (2)0.0654 (6)
C10.6476 (3)0.8679 (3)0.8722 (2)0.0577 (6)
H1A0.71090.90450.81910.069*
C20.6908 (3)0.8716 (4)0.9636 (2)0.0644 (7)
H2A0.78060.91080.97220.077*
C30.5984 (4)0.8163 (4)1.0420 (2)0.0747 (9)
H3A0.62660.81431.10490.090*
C40.4630 (3)0.7635 (4)1.0269 (2)0.0659 (7)
H4A0.39820.72731.07930.079*
C50.4258 (3)0.7655 (3)0.93238 (17)0.0471 (5)
C60.2814 (3)0.7132 (3)0.91130 (15)0.0429 (5)
C70.1518 (3)0.7245 (3)0.97008 (17)0.0494 (5)
H7A0.15700.76661.02390.059*
C80.1461 (3)0.6118 (3)0.81258 (18)0.0526 (6)
H8A0.13940.57240.75770.063*
C90.0207 (3)0.6218 (3)0.87300 (18)0.0478 (5)
C10−0.1216 (3)0.5724 (3)0.8523 (2)0.0555 (6)
C110.7058 (3)0.4967 (3)0.62202 (18)0.0493 (5)
H11A0.71940.45000.68710.059*
C120.7931 (3)0.4422 (3)0.5521 (2)0.0531 (6)
H12A0.86310.36010.56960.064*
C130.7749 (3)0.5111 (3)0.4566 (2)0.0551 (6)
H13A0.83450.47840.40800.066*
C140.6665 (3)0.6305 (3)0.43296 (18)0.0474 (5)
H14A0.65120.67790.36810.057*
C150.5814 (2)0.6782 (2)0.50681 (15)0.0346 (4)
C160.4612 (2)0.8042 (2)0.48494 (15)0.0345 (4)
C170.4369 (3)0.8876 (3)0.39062 (17)0.0487 (5)
H17A0.49910.86470.33980.058*
C180.2663 (2)0.9470 (3)0.53981 (18)0.0453 (5)
H18A0.20470.97120.59040.054*
C190.2421 (2)1.0246 (2)0.44564 (17)0.0407 (4)
C200.1224 (3)1.1448 (3)0.4237 (2)0.0494 (5)
P10.04799 (7)1.12551 (7)0.76794 (5)0.04787 (15)
F50.0408 (3)1.1620 (2)0.65229 (13)0.0903 (6)
F40.2221 (2)1.0737 (3)0.75732 (16)0.0945 (7)
F3−0.1266 (2)1.1778 (3)0.77714 (17)0.0920 (6)
F60.0579 (3)1.0844 (3)0.88231 (14)0.1011 (7)
F10.0880 (3)1.2901 (2)0.7634 (2)0.1208 (9)
F20.0083 (3)0.9602 (2)0.77003 (17)0.0918 (6)
U11U22U33U12U13U23
Ag10.06857 (14)0.07215 (15)0.03810 (11)−0.00412 (10)0.00886 (8)−0.02065 (9)
N10.0422 (10)0.0584 (12)0.0420 (10)0.0000 (8)0.0002 (8)−0.0152 (9)
N20.0525 (11)0.0576 (12)0.0382 (10)−0.0042 (9)0.0012 (8)−0.0152 (8)
N30.0503 (11)0.0603 (12)0.0461 (11)−0.0050 (9)0.0022 (9)−0.0146 (9)
N40.0423 (9)0.0452 (10)0.0400 (9)0.0016 (8)−0.0038 (7)−0.0136 (8)
N50.0372 (9)0.0492 (10)0.0403 (9)0.0015 (7)0.0019 (7)−0.0156 (8)
N60.0467 (10)0.0569 (12)0.0464 (11)0.0084 (9)−0.0023 (8)−0.0088 (9)
N70.0617 (14)0.0812 (17)0.0726 (16)−0.0124 (13)−0.0100 (12)−0.0234 (13)
N80.0524 (12)0.0628 (14)0.0816 (17)0.0149 (11)−0.0132 (12)−0.0223 (12)
C10.0458 (13)0.0699 (17)0.0585 (15)−0.0028 (12)0.0013 (11)−0.0181 (13)
C20.0472 (13)0.083 (2)0.0680 (18)−0.0040 (13)−0.0085 (12)−0.0263 (15)
C30.0706 (18)0.109 (3)0.0515 (16)−0.0126 (17)−0.0169 (14)−0.0258 (16)
C40.0655 (16)0.096 (2)0.0383 (13)−0.0135 (15)−0.0038 (11)−0.0151 (13)
C50.0469 (12)0.0547 (13)0.0395 (11)−0.0005 (10)−0.0023 (9)−0.0114 (10)
C60.0481 (11)0.0473 (12)0.0322 (10)−0.0012 (9)−0.0012 (8)−0.0071 (9)
C70.0528 (13)0.0593 (14)0.0382 (11)−0.0051 (11)0.0016 (9)−0.0156 (10)
C80.0591 (14)0.0607 (14)0.0415 (12)−0.0079 (11)−0.0018 (10)−0.0175 (11)
C90.0507 (12)0.0477 (12)0.0437 (12)−0.0036 (10)−0.0045 (10)−0.0064 (10)
C100.0570 (15)0.0587 (15)0.0513 (14)−0.0068 (12)−0.0052 (11)−0.0116 (11)
C110.0507 (13)0.0499 (13)0.0471 (13)0.0053 (10)−0.0126 (10)−0.0114 (10)
C120.0461 (12)0.0479 (13)0.0665 (16)0.0111 (10)−0.0114 (11)−0.0189 (12)
C130.0518 (13)0.0567 (14)0.0570 (15)0.0116 (11)0.0060 (11)−0.0214 (12)
C140.0487 (12)0.0505 (13)0.0420 (12)0.0065 (10)0.0043 (9)−0.0134 (10)
C150.0311 (9)0.0349 (9)0.0395 (10)−0.0028 (7)0.0001 (7)−0.0121 (8)
C160.0302 (9)0.0368 (10)0.0389 (10)−0.0037 (7)0.0001 (7)−0.0137 (8)
C170.0461 (12)0.0562 (13)0.0402 (12)0.0100 (10)0.0041 (9)−0.0098 (10)
C180.0372 (10)0.0525 (13)0.0480 (12)0.0043 (9)0.0032 (9)−0.0194 (10)
C190.0310 (9)0.0394 (10)0.0540 (13)−0.0015 (8)−0.0045 (8)−0.0148 (9)
C200.0384 (11)0.0507 (13)0.0610 (15)0.0020 (10)−0.0063 (10)−0.0176 (11)
P10.0530 (3)0.0482 (3)0.0428 (3)−0.0012 (3)0.0021 (2)−0.0128 (3)
F50.1156 (16)0.0957 (14)0.0469 (9)0.0363 (12)−0.0066 (10)−0.0060 (9)
F40.0560 (10)0.1330 (19)0.0913 (15)0.0151 (11)−0.0017 (10)−0.0271 (13)
F30.0626 (11)0.1042 (15)0.1056 (16)0.0126 (10)0.0113 (10)−0.0262 (13)
F60.1187 (17)0.140 (2)0.0472 (10)−0.0087 (15)−0.0014 (10)−0.0267 (11)
F10.146 (2)0.0698 (13)0.160 (2)−0.0404 (14)0.0392 (18)−0.0522 (15)
F20.1197 (17)0.0551 (10)0.1022 (16)−0.0126 (10)−0.0138 (13)−0.0163 (10)
Ag1—N42.2887 (18)C5—C61.478 (3)
Ag1—N12.301 (2)C6—C71.393 (3)
Ag1—N22.389 (2)C7—H7A0.9300
Ag1—N52.4714 (19)C8—C91.376 (4)
N1—C51.343 (3)C8—H8A0.9300
N1—C11.342 (3)C9—C101.448 (4)
N2—C81.331 (3)C11—C121.374 (4)
N2—C61.340 (3)C11—H11A0.9300
N3—C71.326 (3)C12—C131.362 (4)
N3—C91.334 (3)C12—H12A0.9300
N4—C151.341 (3)C13—C141.386 (3)
N4—C111.341 (3)C13—H13A0.9300
N5—C161.331 (3)C14—C151.381 (3)
N5—C181.339 (3)C14—H14A0.9300
N6—C191.330 (3)C15—C161.492 (3)
N6—C171.333 (3)C16—C171.393 (3)
N7—C101.134 (4)C17—H17A0.9300
N8—C201.131 (3)C18—C191.375 (3)
C1—C21.371 (4)C18—H18A0.9300
C1—H1A0.9300C19—C201.454 (3)
C2—C31.371 (5)P1—F11.568 (2)
C2—H2A0.9300P1—F61.575 (2)
C3—C41.382 (4)P1—F21.5812 (19)
C3—H3A0.9300P1—F41.5883 (19)
C4—C51.385 (3)P1—F51.5906 (18)
C4—H4A0.9300P1—F31.5908 (19)
N4—Ag1—N1145.43 (7)C8—C9—C10121.0 (2)
N4—Ag1—N2133.18 (7)N7—C10—C9179.3 (3)
N1—Ag1—N272.30 (7)N4—C11—C12123.3 (2)
N4—Ag1—N569.52 (6)N4—C11—H11A118.4
N1—Ag1—N5132.63 (7)C12—C11—H11A118.4
N2—Ag1—N5106.77 (7)C13—C12—C11118.6 (2)
C5—N1—C1118.0 (2)C13—C12—H12A120.7
C5—N1—Ag1115.17 (16)C11—C12—H12A120.7
C1—N1—Ag1123.14 (16)C12—C13—C14119.1 (2)
C8—N2—C6117.4 (2)C12—C13—H13A120.4
C8—N2—Ag1127.48 (16)C14—C13—H13A120.4
C6—N2—Ag1112.57 (15)C15—C14—C13119.2 (2)
C7—N3—C9115.6 (2)C15—C14—H14A120.4
C15—N4—C11117.90 (19)C13—C14—H14A120.4
C15—N4—Ag1119.88 (13)N4—C15—C14121.82 (19)
C11—N4—Ag1121.75 (15)N4—C15—C16117.00 (17)
C16—N5—C18117.68 (19)C14—C15—C16121.18 (19)
C16—N5—Ag1113.32 (13)N5—C16—C17120.12 (19)
C18—N5—Ag1127.61 (14)N5—C16—C15117.60 (18)
C19—N6—C17115.7 (2)C17—C16—C15122.27 (18)
N1—C1—C2123.2 (3)N6—C17—C16122.8 (2)
N1—C1—H1A118.4N6—C17—H17A118.6
C2—C1—H1A118.4C16—C17—H17A118.6
C1—C2—C3118.5 (3)N5—C18—C19120.9 (2)
C1—C2—H2A120.8N5—C18—H18A119.6
C3—C2—H2A120.8C19—C18—H18A119.6
C2—C3—C4119.6 (3)N6—C19—C18122.76 (19)
C2—C3—H3A120.2N6—C19—C20116.0 (2)
C4—C3—H3A120.2C18—C19—C20121.2 (2)
C3—C4—C5118.7 (3)N8—C20—C19179.9 (3)
C3—C4—H4A120.7F1—P1—F691.37 (15)
C5—C4—H4A120.7F1—P1—F2178.75 (15)
N1—C5—C4122.0 (2)F6—P1—F289.84 (13)
N1—C5—C6116.7 (2)F1—P1—F490.26 (15)
C4—C5—C6121.3 (2)F6—P1—F490.18 (13)
N2—C6—C7120.2 (2)F2—P1—F489.45 (13)
N2—C6—C5117.8 (2)F1—P1—F589.97 (15)
C7—C6—C5121.9 (2)F6—P1—F5178.18 (13)
N3—C7—C6122.9 (2)F2—P1—F588.81 (12)
N3—C7—H7A118.6F4—P1—F588.57 (11)
C6—C7—H7A118.6F1—P1—F389.76 (14)
N2—C8—C9121.1 (2)F6—P1—F390.52 (13)
N2—C8—H8A119.4F2—P1—F390.52 (13)
C9—C8—H8A119.4F4—P1—F3179.29 (12)
N3—C9—C8122.9 (2)F5—P1—F390.72 (12)
N3—C9—C10116.1 (2)
N4—Ag1—N1—C5−132.25 (17)C4—C5—C6—C729.9 (4)
N2—Ag1—N1—C511.13 (16)C9—N3—C7—C6−1.4 (4)
N5—Ag1—N1—C5107.90 (18)N2—C6—C7—N32.1 (4)
N4—Ag1—N1—C125.6 (3)C5—C6—C7—N3−179.8 (2)
N2—Ag1—N1—C1169.0 (2)C6—N2—C8—C90.1 (4)
N5—Ag1—N1—C1−94.3 (2)Ag1—N2—C8—C9−160.13 (19)
N4—Ag1—N2—C8−43.4 (3)C7—N3—C9—C80.2 (4)
N1—Ag1—N2—C8164.3 (2)C7—N3—C9—C10−179.2 (2)
N5—Ag1—N2—C834.0 (2)N2—C8—C9—N30.5 (4)
N4—Ag1—N2—C6155.58 (14)N2—C8—C9—C10179.8 (2)
N1—Ag1—N2—C63.24 (16)N3—C9—C10—N711 (29)
N5—Ag1—N2—C6−127.02 (16)C8—C9—C10—N7−169 (100)
N1—Ag1—N4—C15−124.46 (16)C15—N4—C11—C121.3 (4)
N2—Ag1—N4—C15106.73 (17)Ag1—N4—C11—C12−170.83 (19)
N5—Ag1—N4—C1512.60 (15)N4—C11—C12—C130.7 (4)
N1—Ag1—N4—C1147.6 (2)C11—C12—C13—C14−1.9 (4)
N2—Ag1—N4—C11−81.3 (2)C12—C13—C14—C151.1 (4)
N5—Ag1—N4—C11−175.4 (2)C11—N4—C15—C14−2.2 (3)
N4—Ag1—N5—C16−14.09 (14)Ag1—N4—C15—C14170.13 (17)
N1—Ag1—N5—C16134.22 (14)C11—N4—C15—C16177.62 (19)
N2—Ag1—N5—C16−144.66 (14)Ag1—N4—C15—C16−10.1 (2)
N4—Ag1—N5—C18179.8 (2)C13—C14—C15—N41.0 (3)
N1—Ag1—N5—C18−31.9 (2)C13—C14—C15—C16−178.8 (2)
N2—Ag1—N5—C1849.2 (2)C18—N5—C16—C173.1 (3)
C5—N1—C1—C21.9 (4)Ag1—N5—C16—C17−164.53 (17)
Ag1—N1—C1—C2−155.3 (2)C18—N5—C16—C15−177.86 (18)
N1—C1—C2—C30.7 (5)Ag1—N5—C16—C1514.5 (2)
C1—C2—C3—C4−2.2 (5)N4—C15—C16—N5−4.1 (3)
C2—C3—C4—C51.2 (5)C14—C15—C16—N5175.7 (2)
C1—N1—C5—C4−3.0 (4)N4—C15—C16—C17174.9 (2)
Ag1—N1—C5—C4156.0 (2)C14—C15—C16—C17−5.3 (3)
C1—N1—C5—C6177.3 (2)C19—N6—C17—C16−0.9 (4)
Ag1—N1—C5—C6−23.7 (3)N5—C16—C17—N6−2.1 (4)
C3—C4—C5—N11.5 (5)C15—C16—C17—N6178.9 (2)
C3—C4—C5—C6−178.8 (3)C16—N5—C18—C19−1.2 (3)
C8—N2—C6—C7−1.3 (3)Ag1—N5—C18—C19164.36 (16)
Ag1—N2—C6—C7161.78 (18)C17—N6—C19—C182.8 (3)
C8—N2—C6—C5−179.5 (2)C17—N6—C19—C20−179.4 (2)
Ag1—N2—C6—C5−16.4 (3)N5—C18—C19—N6−1.8 (4)
N1—C5—C6—N227.7 (3)N5—C18—C19—C20−179.5 (2)
C4—C5—C6—N2−152.0 (3)N6—C19—C20—N8−163 (100)
N1—C5—C6—C7−150.4 (2)C18—C19—C20—N814 (100)
D—H···AD—HH···AD···AD—H···A
C11—H11A···N7i0.932.473.201 (2)135
C≡N···CgC···Cg (Å)N···Cg (Å)sym. code
C20 N8 Cg23.509 (3)3.519 (2)-x+1,-y+2,-z+1
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯ADAD—H⋯A
C11—H11A⋯N7i0.932.473.201 (2)135

Symmetry code: (i) .

  3 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.  Bis[5-(2-pyrid-yl)pyrazine-2-carbonitrile]-silver(I) tetra-fluorido-borate.

Authors:  Zi-Jia Wang; Fan Zhang; Chong-Qing Wan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-09-08

3.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
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