Bis(4-methyl-3,5-diphenyl-1H-pyrazole-κN 2)silver(I) nitrate

Moayad Hossaini Sadr; Behzad Soltani; James T Engle; Christopher J Ziegler; M Kabirzadeh

doi:10.1107/S1600536811017776

. 2011 May 20;67(Pt 6):m762–m763. doi: 10.1107/S1600536811017776

Bis(4-methyl-3,5-diphenyl-1H-pyrazole-κN ²)silver(I) nitrate

Moayad Hossaini Sadr ^a,^*, Behzad Soltani ^a, James T Engle ^b, Christopher J Ziegler ^b, M Kabirzadeh ^a

PMCID: PMC3120342 PMID: 21754649

Abstract

In the title complex, [Ag(C₁₆H₁₄N₂)₂]NO₃, the geometry around the Ag^I ion is T-shaped with two short Ag—N bonds to the pyrazole ligand and one long Ag—O bond to the nitrate anion. The crystal structure is stabilized by intermolecular N—H⋯O, C—H⋯O and C—H⋯π interactions.

Related literature

For standard bond lengths, see: Allen et al. (1987 ▶). For background to pyrazolates and their complexes, see, for example; Rasika Dias et al. (2007 ▶); Hossaini Sadr et al. (2004 ▶, 2006 ▶, 2008a ▶,b ▶).

Experimental

Crystal data

[Ag(C₁₆H₁₄N₂)₂]NO₃
M _r = 638.46
Triclinic,
a = 10.5529 (12) Å
b = 10.8791 (13) Å
c = 12.8396 (15) Å
α = 80.454 (2)°
β = 68.806 (2)°
γ = 82.398 (2)°
V = 1351.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.79 mm⁻¹
T = 100 K
0.45 × 0.25 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.717, T _max = 0.940
8897 measured reflections
4588 independent reflections
4127 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.029
wR(F ²) = 0.084
S = 1.15
4588 reflections
372 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811017776/jh2288sup1.cif

e-67-0m762-sup1.cif^{(26.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017776/jh2288Isup2.hkl

e-67-0m762-Isup2.hkl^{(224.8KB, hkl)}

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

Table 1. Selected geometric parameters (Å, °).

Ag1—N1	2.141 (2)
Ag1—N3	2.147 (2)
Ag1—O1ⁱ	2.768 (2)

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N1—Ag1—N3	167.23 (9)
N2—N1—C1	105.1 (2)
N2—N1—Ag1	115.79 (17)
C1—N1—Ag1	137.10 (19)
Ag1ⁱ—O1—N5	141.8 (2)

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Symmetry code: (i) Inline graphic .

Table 2. Hydrogen-bond geometry (Å, °).

Cg1 and Cg2 are the centroids of the N3/N4/C17–C19 and C5–C10 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1ⁱ	0.88	1.97	2.686 (3)	137
N4—H4⋯O3ⁱ	0.88	1.98	2.858 (3)	175
C26—H26⋯O3ⁱⁱ	0.95	2.58	3.358 (4)	140
C32—H32⋯O3ⁱ	0.95	2.50	3.145 (4)	125
C12—H12⋯Cg2ⁱⁱⁱ	0.95	2.99	3.437 (4)	111
C30—H30⋯Cg3^iv	0.95	2.98	3.456 (3)	112

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

This research was supported by research fund No. 403/313 from Azarbaijan University of Tarbiat Moallem (MHS and BS).

supplementary crystallographic information

Comment

The chemistry of coinage metals with pyrazole derived ligands has attracted much interest, mainly to their diverse structures and applications in areas such as modeling C—H bond activations. The abundance and variety of pyrazole complexes of copper is in contrast to the small number of the corresponding silver and gold complexes (Rasika Dias et al., 2007). In continuation of our research on pyrazolate complexes (Hossaini Sadr et al., 2008a; Hossaini Sadr et al., 2008b; Hossaini Sadr et al., 2006; Hossaini Sadr et al., 2004), we synthesized the title compound and determined its structure by X-ray diffraction.

The asymmetric unit of the title complex, Fig. 1, comprises a cation complex and a nitrate ion. The bond lengths (Allen, et al., 1987) and angles are within the normal ranges. The geometry around Ag(I) is T-shaped which is coordinated by two pyrazolate ligands and a nitrate ion. The crystal structure is stabilized by the intermolecular N—H···O, C—H···O and C—H···π interactions (Table 1).

Experimental

To an acetone (40 ml) solution of 4-methyl-3,5-diphenyl-1H-pyrazole (0.1 g, 1 mmol) under a dry nitrogen atmosphere, AgNO₃ (0.07 g, 1 mmol) was added and the solution was stirred for 3 h. The resulting mixture was filtered and the precipitate was washed with cold acetone (2 X 10 ml). The bright yellow precipitate was dissolved in acetonitrile and the filtrate was left to evaporate slowly at ambient temperature. Single crystals suitable for X-ray diffraction analysis were obtained after 4 days.