PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): m1087.
Published online 2009 August 19. doi:  10.1107/S160053680903178X
PMCID: PMC2969874

{4-[(Diphenyl­phosphino)methyl­amino]pyridinium-κP}bis­(nitrato-κO)silver(I)

Abstract

In the title mononuclear complex, [Ag(C18H18N2P)(NO3)2], the metal centre is coordinated in a slightly distorted trigonal–planar geometry by the P atom of the phosphine ligand and the O atoms of the two monodentate nitrate anions. In the crystal structure, complex mol­ecules are connected by inter­molecular N—H(...)O hydrogen bonds, forming chains running parallel to the b axis.

Related literature

For related structures, see: Song et al. (2002 [triangle]); Durran et al. (2006 [triangle]); Jiang et al. (2009 [triangle]); Wang et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1087-scheme1.jpg

Experimental

Crystal data

  • [Ag(C18H18N2P)(NO3)2]
  • M r = 525.20
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1087-efi1.jpg
  • a = 7.9760 (9) Å
  • b = 9.6895 (11) Å
  • c = 14.1207 (16) Å
  • α = 86.170 (2)°
  • β = 89.170 (2)°
  • γ = 69.439 (2)°
  • V = 1019.5 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.11 mm−1
  • T = 173 K
  • 0.47 × 0.33 × 0.16 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1998 [triangle]) T min = 0.699, T max = 0.838
  • 8623 measured reflections
  • 4367 independent reflections
  • 3802 reflections with I > 2σ(I)
  • R int = 0.018

Refinement

  • R[F 2 > 2σ(F 2)] = 0.029
  • wR(F 2) = 0.109
  • S = 1.15
  • 4367 reflections
  • 271 parameters
  • H-atom parameters constrained
  • Δρmax = 0.66 e Å−3
  • Δρmin = −0.46 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1998 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680903178X/rz2347sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903178X/rz2347Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by the Natural Science Foundation of Guangxi Province (grant No. 0832100) and the Programme for Excellent Talents in Guangxi Higher Education Institutions.

supplementary crystallographic information

Comment

Silver(I) metal complexes with pyridine-phosphine ligands which contain a soft Lewis base (P) and a hard Lewis acid (N) had been extensively studied so far (Song et al., 2002; Durran et al., 2006; Jiang et al., 2009; Wang et al. 2008). Herein, we report the crystal structure of the title complex.

In the title complex (Fig. 1), the silver(I) metal centre adopts a slightly distorted trigonal-planar geometry provided by the P atom of the phosphine ligand and by the O atoms of two monodentate nitrate anions. The metal is displaced by 0.0629 (3) Å from the plane of the donor atoms. In the crystal structure, the complex molecules are linked by intermolecular N—H···O hydrogen bonds (Table 1, Fig. 2) to form chains running parallel to the b axis.

Experimental

Silver nitrate (0.0168 g, 1 mmol) was dissolved in CH3CN (2 ml) and a solution of N-diphenylphosphinomethyl-4-aminopyridinium (0.0292 g, 1 mmol) in CH3OH (4 ml) was added with stirring for three hours at room temperature. Subsequent diethyl ether diffusion into the solution afforded colourless crystal of the title compound suitable for X-ray analysis.

Refinement

All H atoms were located geometrically and treated as riding atoms, with N—H= 0.88 Å, C—H = 0.95–0.98 Å, and with Uiso(H) = 1.2Ueq(C, N).

Figures

Fig. 1.
The molecular structure of title complex with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Partial packing diagram of the title compound, showing the intermlecular N—H···O hydrogen bonds as dashed lines. H atoms not involved in hydrogen bonding are omitted for clarity.

Crystal data

[Ag(C18H18N2P)(NO3)2]Z = 2
Mr = 525.20F(000) = 528
Triclinic, P1Dx = 1.711 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.9760 (9) ÅCell parameters from 5807 reflections
b = 9.6895 (11) Åθ = 2.7–27.0°
c = 14.1207 (16) ŵ = 1.11 mm1
α = 86.170 (2)°T = 173 K
β = 89.170 (2)°Block, colourless
γ = 69.439 (2)°0.47 × 0.33 × 0.16 mm
V = 1019.5 (2) Å3

Data collection

Bruker SMART CCD area-detector diffractometer4367 independent reflections
Radiation source: fine-focus sealed tube3802 reflections with I > 2σ(I)
graphiteRint = 0.018
ω scansθmax = 27.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 1998)h = −10→9
Tmin = 0.699, Tmax = 0.838k = −12→12
8623 measured reflectionsl = −18→17

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 1.15w = 1/[σ2(Fo2) + (0.0737P)2 + 0.0727P] where P = (Fo2 + 2Fc2)/3
4367 reflections(Δ/σ)max = 0.001
271 parametersΔρmax = 0.66 e Å3
0 restraintsΔρmin = −0.46 e Å3

Special details

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)

xyzUiso*/Ueq
Ag10.46577 (3)0.46190 (2)0.297716 (16)0.03069 (11)
P10.20209 (10)0.64942 (8)0.24168 (5)0.02155 (16)
O10.6827 (3)0.2456 (3)0.24276 (18)0.0391 (5)
O20.4738 (3)0.1861 (3)0.31211 (19)0.0429 (6)
O30.6975 (3)0.0183 (2)0.25015 (18)0.0428 (6)
O40.6546 (3)0.4154 (2)0.43169 (15)0.0311 (5)
O50.7902 (3)0.5171 (2)0.52073 (17)0.0381 (6)
O60.6328 (4)0.6441 (3)0.39968 (18)0.0481 (7)
N10.1753 (3)1.2090 (3)0.45460 (18)0.0283 (5)
H1A0.17741.29630.46670.034*
N20.1655 (3)0.7994 (2)0.40482 (16)0.0219 (5)
H2A0.23570.72710.44280.026*
N30.6180 (4)0.1481 (3)0.26837 (18)0.0288 (5)
N40.6919 (3)0.5284 (3)0.44974 (17)0.0265 (5)
C10.2731 (4)1.0885 (3)0.5089 (2)0.0269 (6)
H1B0.34421.09910.55940.032*
C20.2720 (4)0.9528 (3)0.4930 (2)0.0256 (6)
H2B0.34200.86930.53210.031*
C30.1658 (3)0.9348 (3)0.41738 (19)0.0204 (5)
C40.0664 (4)1.0632 (3)0.3620 (2)0.0231 (6)
H4A−0.00591.05670.31080.028*
C50.0740 (4)1.1971 (3)0.3818 (2)0.0284 (6)
H5A0.00701.28310.34380.034*
C60.0617 (4)0.7590 (3)0.33523 (19)0.0230 (5)
H6A−0.02720.85000.30510.028*
H6B−0.00490.70100.36800.028*
C70.0424 (4)0.5829 (3)0.18720 (19)0.0229 (5)
C80.0942 (4)0.4339 (3)0.1700 (2)0.0325 (7)
H8A0.21350.36970.18350.039*
C9−0.0290 (5)0.3790 (3)0.1330 (3)0.0394 (8)
H9A0.00680.27720.12170.047*
C10−0.1997 (5)0.4697 (4)0.1129 (2)0.0375 (8)
H10A−0.28310.43100.08840.045*
C11−0.2522 (4)0.6186 (4)0.1281 (2)0.0378 (8)
H11A−0.37110.68220.11290.045*
C12−0.1322 (4)0.6748 (3)0.1652 (2)0.0335 (7)
H12A−0.16920.77700.17580.040*
C130.2342 (4)0.7867 (3)0.15637 (19)0.0227 (5)
C140.1854 (4)0.7949 (4)0.0613 (2)0.0339 (7)
H14A0.13030.72970.04040.041*
C150.2167 (5)0.8975 (4)−0.0029 (2)0.0424 (8)
H15A0.18580.9011−0.06800.051*
C160.2934 (5)0.9955 (4)0.0282 (3)0.0414 (8)
H16A0.31041.0689−0.01500.050*
C170.3444 (5)0.9857 (4)0.1215 (3)0.0378 (8)
H17A0.39771.05190.14250.045*
C180.3189 (4)0.8801 (3)0.1855 (2)0.0285 (6)
H18A0.35930.87160.24930.034*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ag10.03087 (16)0.02167 (15)0.03252 (16)0.00010 (10)−0.00920 (10)−0.00312 (9)
P10.0243 (4)0.0165 (3)0.0215 (3)−0.0036 (3)−0.0032 (3)−0.0036 (3)
O10.0364 (13)0.0254 (12)0.0523 (15)−0.0074 (10)0.0050 (11)−0.0014 (10)
O20.0350 (13)0.0333 (13)0.0535 (15)−0.0049 (10)0.0092 (11)0.0023 (11)
O30.0476 (14)0.0205 (11)0.0509 (15)0.0013 (10)−0.0151 (11)−0.0095 (10)
O40.0377 (12)0.0186 (10)0.0362 (12)−0.0080 (9)−0.0105 (9)−0.0035 (8)
O50.0479 (14)0.0260 (12)0.0433 (13)−0.0169 (11)−0.0224 (11)0.0037 (10)
O60.0708 (18)0.0321 (13)0.0454 (15)−0.0250 (13)−0.0217 (13)0.0142 (11)
N10.0319 (13)0.0239 (13)0.0343 (14)−0.0151 (11)0.0092 (11)−0.0096 (10)
N20.0283 (12)0.0136 (11)0.0207 (11)−0.0034 (9)−0.0046 (9)−0.0004 (8)
N30.0320 (14)0.0225 (13)0.0275 (13)−0.0035 (11)−0.0083 (10)−0.0036 (10)
N40.0292 (13)0.0214 (12)0.0271 (12)−0.0068 (10)−0.0038 (10)0.0000 (10)
C10.0248 (14)0.0313 (16)0.0276 (15)−0.0123 (12)0.0047 (11)−0.0092 (12)
C20.0234 (14)0.0331 (16)0.0205 (13)−0.0096 (12)0.0016 (10)−0.0042 (11)
C30.0171 (12)0.0223 (14)0.0205 (13)−0.0049 (10)0.0035 (10)−0.0043 (10)
C40.0230 (13)0.0214 (14)0.0240 (14)−0.0064 (11)−0.0002 (10)−0.0025 (11)
C50.0286 (15)0.0275 (16)0.0277 (15)−0.0085 (12)0.0053 (11)−0.0001 (11)
C60.0243 (13)0.0240 (14)0.0202 (13)−0.0074 (11)−0.0008 (10)−0.0039 (10)
C70.0267 (14)0.0198 (13)0.0229 (13)−0.0086 (11)−0.0025 (11)−0.0024 (10)
C80.0340 (17)0.0243 (16)0.0362 (17)−0.0058 (13)−0.0082 (13)−0.0045 (12)
C90.053 (2)0.0170 (15)0.049 (2)−0.0121 (15)−0.0120 (16)−0.0056 (13)
C100.0388 (18)0.0405 (19)0.0408 (18)−0.0222 (16)−0.0018 (14)−0.0082 (14)
C110.0276 (16)0.043 (2)0.0406 (19)−0.0075 (14)0.0001 (13)−0.0133 (15)
C120.0316 (16)0.0225 (16)0.0429 (18)−0.0033 (13)−0.0039 (13)−0.0111 (13)
C130.0206 (13)0.0209 (13)0.0233 (13)−0.0030 (11)0.0012 (10)−0.0025 (10)
C140.0360 (17)0.0389 (18)0.0293 (16)−0.0166 (15)−0.0054 (13)0.0011 (13)
C150.0381 (19)0.063 (2)0.0269 (16)−0.0213 (18)−0.0099 (13)0.0133 (15)
C160.0333 (17)0.0385 (19)0.049 (2)−0.0107 (15)0.0033 (15)0.0135 (15)
C170.0393 (19)0.0294 (17)0.048 (2)−0.0156 (15)0.0118 (15)−0.0065 (14)
C180.0282 (15)0.0315 (16)0.0276 (15)−0.0118 (13)0.0031 (12)−0.0081 (12)

Geometric parameters (Å, °)

Ag1—P12.3500 (8)C5—H5A0.9500
Ag1—O42.354 (2)C6—H6A0.9900
Ag1—O12.370 (2)C6—H6B0.9900
P1—C71.817 (3)C7—C121.391 (4)
P1—C131.817 (3)C7—C81.393 (4)
P1—C61.854 (3)C8—C91.393 (4)
O1—N31.257 (3)C8—H8A0.9500
O2—N31.246 (3)C9—C101.358 (5)
O3—N31.236 (3)C9—H9A0.9500
O4—N41.273 (3)C10—C111.385 (5)
O5—N41.256 (3)C10—H10A0.9500
O6—N41.229 (3)C11—C121.381 (5)
N1—C11.349 (4)C11—H11A0.9500
N1—C51.352 (4)C12—H12A0.9500
N1—H1A0.8800C13—C181.390 (4)
N2—C31.336 (3)C13—C141.393 (4)
N2—C61.452 (3)C14—C151.387 (5)
N2—H2A0.8800C14—H14A0.9500
C1—C21.351 (4)C15—C161.394 (5)
C1—H1B0.9500C15—H15A0.9500
C2—C31.430 (4)C16—C171.371 (5)
C2—H2B0.9500C16—H16A0.9500
C3—C41.408 (4)C17—C181.386 (4)
C4—C51.368 (4)C17—H17A0.9500
C4—H4A0.9500C18—H18A0.9500
P1—Ag1—O4136.46 (5)P1—C6—H6A109.0
P1—Ag1—O1138.31 (7)N2—C6—H6B109.0
O4—Ag1—O184.99 (8)P1—C6—H6B109.0
C7—P1—C13105.94 (13)H6A—C6—H6B107.8
C7—P1—C6100.58 (13)C12—C7—C8118.8 (3)
C13—P1—C6104.39 (13)C12—C7—P1122.2 (2)
C7—P1—Ag1114.33 (10)C8—C7—P1119.0 (2)
C13—P1—Ag1115.36 (9)C7—C8—C9120.0 (3)
C6—P1—Ag1114.65 (9)C7—C8—H8A120.0
N3—O1—Ag1102.13 (18)C9—C8—H8A120.0
N4—O4—Ag1111.82 (16)C10—C9—C8120.7 (3)
C1—N1—C5120.7 (3)C10—C9—H9A119.7
C1—N1—H1A119.7C8—C9—H9A119.7
C5—N1—H1A119.7C9—C10—C11120.0 (3)
C3—N2—C6126.9 (2)C9—C10—H10A120.0
C3—N2—H2A116.5C11—C10—H10A120.0
C6—N2—H2A116.5C12—C11—C10120.2 (3)
O3—N3—O2121.7 (3)C12—C11—H11A119.9
O3—N3—O1120.0 (3)C10—C11—H11A119.9
O2—N3—O1118.3 (3)C11—C12—C7120.4 (3)
O6—N4—O5121.6 (2)C11—C12—H12A119.8
O6—N4—O4121.0 (2)C7—C12—H12A119.8
O5—N4—O4117.5 (2)C18—C13—C14119.1 (3)
N1—C1—C2121.3 (3)C18—C13—P1119.2 (2)
N1—C1—H1B119.3C14—C13—P1121.5 (2)
C2—C1—H1B119.3C15—C14—C13120.4 (3)
C1—C2—C3120.1 (3)C15—C14—H14A119.8
C1—C2—H2B120.0C13—C14—H14A119.8
C3—C2—H2B120.0C14—C15—C16119.8 (3)
N2—C3—C4124.7 (2)C14—C15—H15A120.1
N2—C3—C2118.4 (3)C16—C15—H15A120.1
C4—C3—C2116.9 (3)C17—C16—C15119.7 (3)
C5—C4—C3120.0 (3)C17—C16—H16A120.1
C5—C4—H4A120.0C15—C16—H16A120.1
C3—C4—H4A120.0C16—C17—C18120.8 (3)
N1—C5—C4121.0 (3)C16—C17—H17A119.6
N1—C5—H5A119.5C18—C17—H17A119.6
C4—C5—H5A119.5C17—C18—C13120.1 (3)
N2—C6—P1112.86 (19)C17—C18—H18A120.0
N2—C6—H6A109.0C13—C18—H18A120.0
O4—Ag1—P1—C7−139.96 (13)C13—P1—C7—C12−63.3 (3)
O1—Ag1—P1—C747.87 (14)C6—P1—C7—C1245.2 (3)
O4—Ag1—P1—C1396.81 (13)Ag1—P1—C7—C12168.5 (2)
O1—Ag1—P1—C13−75.36 (13)C13—P1—C7—C8119.1 (2)
O4—Ag1—P1—C6−24.55 (14)C6—P1—C7—C8−132.4 (2)
O1—Ag1—P1—C6163.29 (13)Ag1—P1—C7—C8−9.1 (3)
P1—Ag1—O1—N3−89.92 (19)C12—C7—C8—C9−1.1 (5)
O4—Ag1—O1—N395.49 (19)P1—C7—C8—C9176.6 (3)
P1—Ag1—O4—N4−46.8 (2)C7—C8—C9—C100.3 (5)
O1—Ag1—O4—N4128.01 (19)C8—C9—C10—C110.8 (6)
Ag1—O1—N3—O3179.4 (2)C9—C10—C11—C12−1.1 (5)
Ag1—O1—N3—O2−0.7 (3)C10—C11—C12—C70.3 (5)
Ag1—O4—N4—O6−0.5 (4)C8—C7—C12—C110.7 (5)
Ag1—O4—N4—O5179.1 (2)P1—C7—C12—C11−176.9 (3)
C5—N1—C1—C2−0.5 (4)C7—P1—C13—C18166.2 (2)
N1—C1—C2—C30.0 (4)C6—P1—C13—C1860.5 (3)
C6—N2—C3—C4−1.9 (4)Ag1—P1—C13—C18−66.2 (2)
C6—N2—C3—C2177.3 (2)C7—P1—C13—C14−17.5 (3)
C1—C2—C3—N2−178.8 (3)C6—P1—C13—C14−123.2 (3)
C1—C2—C3—C40.4 (4)Ag1—P1—C13—C14110.0 (2)
N2—C3—C4—C5178.9 (3)C18—C13—C14—C15−1.7 (5)
C2—C3—C4—C5−0.2 (4)P1—C13—C14—C15−177.9 (3)
C1—N1—C5—C40.7 (4)C13—C14—C15—C16−1.6 (5)
C3—C4—C5—N1−0.3 (4)C14—C15—C16—C172.7 (6)
C3—N2—C6—P1111.1 (3)C15—C16—C17—C18−0.6 (5)
C7—P1—C6—N2167.0 (2)C16—C17—C18—C13−2.7 (5)
C13—P1—C6—N2−83.4 (2)C14—C13—C18—C173.8 (4)
Ag1—P1—C6—N243.8 (2)P1—C13—C18—C17−179.9 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O5i0.881.932.807 (3)172
N2—H2A···O4ii0.882.163.013 (3)162
N2—H2A···O5ii0.882.473.075 (3)127

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2347).

References

  • Bruker (1998). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Durran, S. E., Smith, M. B., Dale, S. H., Coles, S. J., Hursthouse, M. B. & Light, M. E. (2006). Inorg. Chim. Acta, 359, 2980–2988.
  • Jiang, X.-F., Lian, H.-C., Min, Z., Wang, X.-J. & Lin, J.-H. (2009). Acta Cryst. E65, m597–m598. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Song, H.-B., Zhang, Z.-Z. & Mak, T. C. W. (2002). J. Chem. Soc. Dalton Trans. pp. 1336–1343.
  • Wang, X.-J., Gui, L.-C., Ni, Q.-L., Liao, Y.-F., Jiang, X.-F., Tang, L.-H., Zhang, Z. & Wu, Q. (2008). CrystEngComm, 10, 1003–1010.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography