Bis[5-(2-naphth­yl)-1H-pyrazole-κN2]silver(I) nitrate

Wang, Z.-Y.; Zhang, P.-P.; Yang, G.; Ng, S.W.

doi:10.1107/S1600536809028645

metal-organic compounds

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Volume 65| Part 8| August 2009| Page m980

doi:10.1107/S1600536809028645

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Bis[5-(2-naphthyl)-1H-pyrazole-κN²]silver(I) nitrate

Zhao-Yang Wang,^a Pei-Pei Zhang,^a Guang Yang ^a and Seik Weng Ng ^b ^*

^aDepartment of Chemistry, Zhengzhou University, Zhengzhou 450001, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 20 July 2009; accepted 20 July 2009; online 25 July 2009)

The Ag atom in the title compound, [Ag(C₁₃H₁₀N₂)₂]NO₃, shows an approximately linear coordination [N–Ag–N 162.6 (4)°]. The coordination geometry is distorted towards square-planar owing to two long Ag⋯O interactions [Ag⋯O = 2.634 (15) and 2.861 (13) Å]. In the crystal structure, the Ag atom lies on a special position of 2 site symmetry; the nitrate anion is disordered about the special position. The crystal under investigation was a racemic twin with a 33% minor twin component.

Related literature

This structure is the first report of a metal complex of the 5-(2-naphthyl)-1H-pyrazole; for the synthesis of this N-heterocycle, see: Yang & Raptis (2003 ).

Experimental

Crystal data

[Ag(C₁₃H₁₀N₂)₂]NO₃
M_r = 558.34
Monoclinic, C 2
a = 13.911 (6) Å
b = 7.340 (1) Å
c = 12.669 (5) Å
β = 113.43 (2)°
V = 1186.9 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.89 mm⁻¹
T = 291 K
0.20 × 0.18 × 0.16 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.843, T_max = 0.871
2268 measured reflections
2056 independent reflections
1752 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.174
S = 1.09
2056 reflections
179 parameters
32 restraints
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.48 e Å⁻³
Absolute structure: Flack (1983 ), 353 Friedel pairs
Flack parameter: 0.33 (8)

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809028645/xu2561sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809028645/xu2561Isup2.hkl

checkCIF report

Related literature top

This structure is the first report of a metal complex of the 3-(2-naphthyl)pyrazole; for the synthesis of this N-heterocycle, see: Yang & Raptis (2003).

Experimental top

3-(2-Naphthyl)pyrazole was prepared according to the literature method (Yang & Raptis, 2003). An acetonitrile solution (2 ml) of silver nitrate (0.02 mmol, 3.4 mg) was mixed with an ethanol solution (1 ml) of 3-(2-naphthyl)pyrazole (0.02 mmol, 4 mg). The pH value of the mixture was adjusted to about 5 by dilute nitric acid. The resulting solution was allowed to evaporate for two weeks to yield colorless crystals in 60% yield.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot of the [Ag(C₁₃H₁₀N₂)₂][NO₃], displacement ellipsoids are drawn at the 50% probability level. The nitrate anion is disordered about a special position; the disorder is not shown.

Bis[5-(2-naphthyl)-1H-pyrazole-κN²]silver(I) nitrate top

Crystal data top

[Ag(C₁₃H₁₀N₂)₂]NO₃	F(000) = 564
M_r = 558.34	D_x = 1.562 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 2056 reflections
a = 13.911 (6) Å	θ = 1.8–27.5°
b = 7.340 (1) Å	µ = 0.89 mm⁻¹
c = 12.669 (5) Å	T = 291 K
β = 113.43 (2)°	Block, colorless
V = 1186.9 (7) Å³	0.20 × 0.18 × 0.16 mm
Z = 2

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	2056 independent reflections
Radiation source: fine-focus sealed tube	1752 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −17→8
T_min = 0.843, T_max = 0.871	k = −9→7
2268 measured reflections	l = −14→16

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.061	w = 1/[σ²(F_o²) + (0.1009P)² + 2.0218P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.174	(Δ/σ)_max = 0.001
S = 1.09	Δρ_max = 0.36 e Å⁻³
2056 reflections	Δρ_min = −0.48 e Å⁻³
179 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
32 restraints	Extinction coefficient: 0.010 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 353 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.33 (8)

Crystal data top

[Ag(C₁₃H₁₀N₂)₂]NO₃	V = 1186.9 (7) Å³
M_r = 558.34	Z = 2
Monoclinic, C2	Mo Kα radiation
a = 13.911 (6) Å	µ = 0.89 mm⁻¹
b = 7.340 (1) Å	T = 291 K
c = 12.669 (5) Å	0.20 × 0.18 × 0.16 mm
β = 113.43 (2)°

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	2056 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1752 reflections with I > 2σ(I)
T_min = 0.843, T_max = 0.871	R_int = 0.061
2268 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	H-atom parameters constrained
wR(F²) = 0.174	Δρ_max = 0.36 e Å⁻³
S = 1.09	Δρ_min = −0.48 e Å⁻³
2056 reflections	Absolute structure: Flack (1983), 353 Friedel pairs
179 parameters	Absolute structure parameter: 0.33 (8)
32 restraints

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ag1	0.5000	0.5000 (2)	0.5000	0.0696 (4)
O1	0.5305 (13)	0.8398 (18)	0.4537 (12)	0.079 (4)	0.50
O2	0.4805 (13)	1.1184 (16)	0.4497 (12)	0.078 (4)	0.50
O3	0.4805 (13)	0.9378 (17)	0.5844 (11)	0.079 (4)	0.50
N1	0.6133 (6)	0.4563 (10)	0.4293 (6)	0.060 (2)
N2	0.6235 (6)	0.2913 (10)	0.3832 (6)	0.0565 (16)
H2	0.5892	0.1907	0.3868	0.068*
N3	0.4971 (9)	0.9654 (11)	0.4961 (9)	0.062 (3)	0.50
C1	0.6779 (7)	0.5684 (15)	0.4085 (8)	0.068 (2)
H1	0.6879	0.6898	0.4312	0.082*
C2	0.7299 (7)	0.479 (3)	0.3471 (7)	0.068 (3)
H2A	0.7788	0.5297	0.3225	0.082*
C3	0.6928 (7)	0.3009 (12)	0.3311 (7)	0.0546 (18)
C4	0.7151 (6)	0.1443 (12)	0.2722 (7)	0.0537 (18)
C5	0.6475 (6)	−0.008 (3)	0.2316 (6)	0.0616 (18)
H5	0.5874	−0.0157	0.2467	0.074*
C6	0.6685 (8)	−0.1416 (16)	0.1720 (8)	0.070 (2)
H6	0.6211	−0.2367	0.1431	0.084*
C7	0.7620 (8)	−0.1405 (17)	0.1522 (8)	0.067 (2)
C8	0.7883 (9)	−0.282 (2)	0.0913 (9)	0.080 (3)
H8	0.7440	−0.3821	0.0639	0.096*
C9	0.8788 (10)	−0.271 (2)	0.0733 (9)	0.096 (4)
H9	0.8948	−0.3637	0.0328	0.115*
C10	0.9456 (8)	−0.130 (3)	0.1125 (10)	0.094 (4)
H10	1.0069	−0.1275	0.0997	0.113*
C11	0.9243 (6)	0.009 (4)	0.1703 (6)	0.082 (3)
H11	0.9719	0.1039	0.1966	0.098*
C12	0.8311 (6)	0.014 (3)	0.1924 (6)	0.060 (2)
C13	0.8064 (6)	0.1497 (16)	0.2520 (8)	0.063 (2)
H13	0.8519	0.2479	0.2795	0.075*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0884 (6)	0.0661 (6)	0.0753 (6)	0.000	0.0547 (5)	0.000
O1	0.077 (7)	0.070 (8)	0.097 (8)	0.012 (6)	0.043 (6)	−0.013 (7)
O2	0.089 (8)	0.058 (7)	0.093 (8)	0.009 (6)	0.043 (7)	0.006 (6)
O3	0.085 (7)	0.088 (9)	0.076 (7)	0.007 (6)	0.045 (6)	0.005 (6)
N1	0.076 (4)	0.052 (6)	0.062 (4)	0.002 (3)	0.039 (3)	−0.003 (3)
N2	0.072 (4)	0.050 (4)	0.056 (4)	−0.001 (3)	0.034 (4)	−0.004 (3)
N3	0.054 (4)	0.071 (9)	0.067 (5)	0.001 (10)	0.029 (4)	−0.005 (10)
C1	0.071 (5)	0.074 (6)	0.060 (5)	−0.009 (4)	0.027 (4)	−0.003 (4)
C2	0.068 (4)	0.072 (9)	0.068 (4)	−0.003 (6)	0.033 (3)	0.001 (6)
C3	0.060 (4)	0.057 (4)	0.054 (4)	0.001 (3)	0.029 (4)	0.004 (3)
C4	0.055 (4)	0.053 (4)	0.058 (5)	0.005 (3)	0.028 (4)	0.009 (4)
C5	0.071 (4)	0.060 (5)	0.067 (4)	0.008 (7)	0.041 (3)	0.006 (8)
C6	0.075 (5)	0.074 (6)	0.064 (6)	−0.004 (5)	0.031 (5)	0.002 (5)
C7	0.077 (5)	0.085 (7)	0.048 (5)	0.008 (5)	0.034 (4)	0.004 (4)
C8	0.090 (6)	0.089 (8)	0.068 (5)	0.011 (6)	0.037 (5)	−0.017 (6)
C9	0.108 (9)	0.124 (11)	0.065 (6)	0.030 (8)	0.043 (6)	−0.015 (7)
C10	0.053 (5)	0.160 (14)	0.066 (6)	0.022 (6)	0.019 (5)	−0.023 (7)
C11	0.053 (4)	0.141 (10)	0.055 (4)	0.004 (10)	0.024 (3)	−0.018 (11)
C12	0.056 (3)	0.081 (7)	0.044 (3)	0.002 (7)	0.021 (3)	0.003 (7)
C13	0.051 (4)	0.091 (7)	0.056 (5)	−0.001 (4)	0.032 (4)	−0.004 (4)

Geometric parameters (Å, º) top

Ag1—N1ⁱ	2.124 (7)	C4—C5	1.42 (2)
Ag1—N1	2.124 (7)	C5—C6	1.34 (2)
Ag1—O1	2.634 (15)	C5—H5	0.9300
Ag1—O2ⁱⁱ	2.861 (13)	C6—C7	1.419 (13)
O1—N3	1.246 (10)	C6—H6	0.9300
O2—N3	1.245 (10)	C7—C8	1.427 (15)
O3—N3	1.246 (10)	C7—C12	1.44 (2)
N1—C1	1.319 (12)	C8—C9	1.369 (17)
N1—N2	1.375 (10)	C8—H8	0.9300
N2—C3	1.370 (11)	C9—C10	1.35 (2)
N2—H2	0.8900	C9—H9	0.9300
C1—C2	1.416 (16)	C10—C11	1.35 (3)
C1—H1	0.9300	C10—H10	0.9300
C2—C3	1.39 (2)	C11—C12	1.432 (10)
C2—H2A	0.9300	C11—H11	0.9300
C3—C4	1.469 (12)	C12—C13	1.38 (2)
C4—C13	1.393 (11)	C13—H13	0.9300

N1ⁱ—Ag1—N1	162.6 (4)	C6—C5—C4	121.3 (7)
N1ⁱ—Ag1—O1	116.7 (4)	C6—C5—H5	119.4
N1—Ag1—O1	80.6 (4)	C4—C5—H5	119.4
N1ⁱ—Ag1—O2ⁱⁱ	85.7 (4)	C5—C6—C7	121.2 (10)
N1—Ag1—O2ⁱⁱ	77.2 (4)	C5—C6—H6	119.4
O1—Ag1—O2ⁱⁱ	152.4 (5)	C7—C6—H6	119.4
N3—O1—Ag1	119.0 (7)	C6—C7—C8	122.8 (11)
C1—N1—N2	105.7 (7)	C6—C7—C12	118.1 (10)
C1—N1—Ag1	131.9 (7)	C8—C7—C12	119.1 (9)
N2—N1—Ag1	122.0 (5)	C9—C8—C7	119.8 (12)
C3—N2—N1	111.7 (7)	C9—C8—H8	120.1
C3—N2—H2	124.1	C7—C8—H8	120.1
N1—N2—H2	124.1	C10—C9—C8	122.0 (11)
O2—N3—O1	119.7 (7)	C10—C9—H9	119.0
O2—N3—O3	120.3 (7)	C8—C9—H9	119.0
O1—N3—O3	120.0 (7)	C11—C10—C9	120.7 (11)
N1—C1—C2	111.1 (12)	C11—C10—H10	119.6
N1—C1—H1	124.5	C9—C10—H10	119.6
C2—C1—H1	124.5	C10—C11—C12	122 (2)
C3—C2—C1	105.8 (9)	C10—C11—H11	118.8
C3—C2—H2A	127.1	C12—C11—H11	118.8
C1—C2—H2A	127.1	C13—C12—C11	124.7 (18)
C2—C3—N2	105.6 (7)	C13—C12—C7	119.2 (7)
C2—C3—C4	132.0 (7)	C11—C12—C7	116.1 (17)
N2—C3—C4	122.4 (8)	C12—C13—C4	121.7 (10)
C13—C4—C5	118.4 (8)	C12—C13—H13	119.2
C13—C4—C3	117.6 (8)	C4—C13—H13	119.2
C5—C4—C3	123.9 (8)

N1ⁱ—Ag1—O1—N3	15.5 (10)	C2—C3—C4—C5	−158.6 (11)
N1—Ag1—O1—N3	−166.2 (9)	N2—C3—C4—C5	20.6 (14)
O2ⁱⁱ—Ag1—O1—N3	157.0 (11)	C13—C4—C5—C6	−2.1 (16)
N1ⁱ—Ag1—N1—C1	−170.0 (8)	C3—C4—C5—C6	175.7 (10)
O1—Ag1—N1—C1	15.2 (9)	C4—C5—C6—C7	3.3 (17)
O2ⁱⁱ—Ag1—N1—C1	178.7 (9)	C5—C6—C7—C8	178.5 (11)
N1ⁱ—Ag1—N1—N2	17.3 (6)	C5—C6—C7—C12	−3.4 (15)
O1—Ag1—N1—N2	−157.4 (8)	C6—C7—C8—C9	178.8 (10)
O2ⁱⁱ—Ag1—N1—N2	6.0 (6)	C12—C7—C8—C9	0.8 (16)
C1—N1—N2—C3	−1.4 (10)	C7—C8—C9—C10	0.7 (19)
Ag1—N1—N2—C3	173.0 (5)	C8—C9—C10—C11	−1 (2)
Ag1—O1—N3—O2	−157.6 (9)	C9—C10—C11—C12	0 (2)
Ag1—O1—N3—O3	22.4 (10)	C10—C11—C12—C13	179.1 (13)
N2—N1—C1—C2	0.9 (10)	C10—C11—C12—C7	2 (2)
Ag1—N1—C1—C2	−172.6 (6)	C6—C7—C12—C13	2.5 (16)
N1—C1—C2—C3	−0.2 (11)	C8—C7—C12—C13	−179.5 (11)
C1—C2—C3—N2	−0.7 (10)	C6—C7—C12—C11	−179.9 (11)
C1—C2—C3—C4	178.6 (9)	C8—C7—C12—C11	−1.8 (16)
N1—N2—C3—C2	1.3 (10)	C11—C12—C13—C4	−178.8 (12)
N1—N2—C3—C4	−178.1 (8)	C7—C12—C13—C4	−1.4 (17)
C2—C3—C4—C13	19.2 (15)	C5—C4—C13—C12	1.2 (15)
N2—C3—C4—C13	−161.6 (8)	C3—C4—C13—C12	−176.7 (10)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱⁱ	0.89	2.04	2.76 (2)	137
N2—H2···O3ⁱⁱⁱ	0.89	2.19	3.08 (2)	173

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

Experimental details

Crystal data
Chemical formula	[Ag(C₁₃H₁₀N₂)₂]NO₃
M_r	558.34
Crystal system, space group	Monoclinic, C2
Temperature (K)	291
a, b, c (Å)	13.911 (6), 7.340 (1), 12.669 (5)
β (°)	113.43 (2)
V (Å³)	1186.9 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.89
Crystal size (mm)	0.20 × 0.18 × 0.16

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.843, 0.871
No. of measured, independent and observed [I > 2σ(I)] reflections	2268, 2056, 1752
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.174, 1.09
No. of reflections	2056
No. of parameters	179
No. of restraints	32
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.48
Absolute structure	Flack (1983), 353 Friedel pairs
Absolute structure parameter	0.33 (8)

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Acknowledgements

We thank the Education Department of Henan Province, Zhengzhou University and the University of Malaya for supporting this study.

References

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