Bis[(E)-N-(pyridin-3-yl-methyl-idene)hydroxyl-amine-κN(1)]silver(I) perchlorate.

Each of the ions in the title salt, [Ag(C(6)H(6)N(2)O)(2)]ClO(4), is completed by the application of crystallographic twofold symmetry. The Ag(I) atom is coordinated by two pyridine N atoms in an almost linear fashion [N-Ag-N = 170.0 (2)°], with the T-shaped coordination geometry being completed by a weakly associated perchlorate-O atom. Supra-molecular zigzag chains along [100] mediated by O-H⋯N hydrogen bonds [as parts of R(2) (2)(6) loops] feature in the crystal packing. The perchlorate O atoms are disordered over two sets of sites in a statistical ratio.

Related literature

For structural diversity in the structures of silver salts, see: Kundu et al. (2010 ▶). For related structures, see: Abu-Youssef et al. (2010 ▶); Xu et al. (2012 ▶).

Experimental

Crystal data

[Ag(C6H6N2O)2]ClO4

M = 451.58

Monoclinic,

a = 15.382 (5) Å

b = 8.234 (3) Å

c = 13.320 (4) Å

β = 111.531 (15)°

V = 1569.3 (8) Å3

Z = 4

Mo Kα radiation

μ = 1.49 mm−1

T = 293 K

0.18 × 0.16 × 0.14 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.449, T max = 1.000

7501 measured reflections

1795 independent reflections

1176 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.147

S = 1.06

1795 reflections

129 parameters

34 restraints

H-atom parameters constrained

Δρmax = 0.74 e Å−3

Δρmin = −0.49 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalClear (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 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publicatioical">n: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812019290/hb6761sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019290/hb6761Isup2.hkl

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

[Ag(C6H6N2O)2]ClO4	F(000) = 896
Mr = 451.58	Dx = 1.911 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3613 reflections
a = 15.382 (5) Å	θ = 3.0–27.5°
b = 8.234 (3) Å	µ = 1.49 mm−1
c = 13.320 (4) Å	T = 293 K
β = 111.531 (15)°	Prism, colourless
V = 1569.3 (8) Å3	0.18 × 0.16 × 0.14 mm
Z = 4

Rigaku R-AXIS RAPID IP diffractometer	1795 independent reflections
Radiation source: fine-focus sealed tube	1176 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
ω scan	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −19→19
Tmin = 0.449, Tmax = 1.000	k = −10→10
7501 measured reflections	l = −17→17

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0776P)2 + 1.2356P] where P = (Fo2 + 2Fc2)/3
1795 reflections	(Δ/σ)max = 0.001
129 parameters	Δρmax = 0.74 e Å−3
34 restraints	Δρmin = −0.49 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ag	1.0000	0.04678 (8)	0.7500	0.0718 (3)
Cl	1.0000	−0.4118 (3)	0.7500	0.0779 (6)
O1	0.5863 (3)	0.6168 (5)	0.5648 (4)	0.0819 (13)
H1o	0.5297	0.6370	0.5298	0.123*
N1	0.8519 (3)	0.0695 (5)	0.6720 (4)	0.0573 (11)
N2	0.6021 (3)	0.4515 (5)	0.5606 (4)	0.0603 (12)
C1	0.7951 (4)	−0.0529 (6)	0.6259 (5)	0.0617 (14)
H1	0.8207	−0.1559	0.6285	0.074*
C2	0.7003 (4)	−0.0342 (7)	0.5744 (5)	0.0645 (14)
H2	0.6630	−0.1234	0.5437	0.077*
C3	0.6612 (4)	0.1150 (7)	0.5686 (4)	0.0587 (13)
H3	0.5971	0.1289	0.5337	0.070*
C4	0.7187 (3)	0.2477 (6)	0.6158 (4)	0.0495 (11)
C5	0.8130 (3)	0.2174 (7)	0.6658 (4)	0.0544 (12)
H5	0.8521	0.3044	0.6971	0.065*
C6	0.6859 (4)	0.4136 (7)	0.6113 (4)	0.0571 (12)
H6	0.7283	0.4943	0.6469	0.068*
O2	1.0050 (8)	−0.2768 (10)	0.6778 (8)	0.105 (3)	0.50
O3	0.9040 (6)	−0.4057 (13)	0.7376 (10)	0.110 (4)	0.50
O4	1.0044 (7)	−0.5524 (9)	0.6836 (7)	0.089 (3)	0.50
O5	1.0649 (10)	−0.4065 (18)	0.8439 (7)	0.171 (6)	0.50

	U11	U22	U33	U12	U13	U23
Ag	0.0392 (4)	0.0813 (5)	0.0859 (5)	0.000	0.0121 (3)	0.000
Cl	0.0624 (13)	0.0605 (12)	0.1049 (17)	0.000	0.0238 (13)	0.000
O1	0.064 (3)	0.054 (2)	0.106 (3)	0.005 (2)	0.005 (3)	0.007 (2)
N1	0.042 (2)	0.061 (3)	0.063 (3)	−0.0016 (19)	0.013 (2)	0.000 (2)
N2	0.054 (3)	0.054 (3)	0.066 (3)	0.005 (2)	0.013 (2)	0.006 (2)
C1	0.056 (3)	0.051 (3)	0.072 (3)	0.000 (2)	0.017 (3)	0.000 (3)
C2	0.048 (3)	0.058 (3)	0.075 (4)	−0.009 (3)	0.009 (3)	−0.006 (3)
C3	0.040 (3)	0.068 (3)	0.060 (3)	−0.003 (3)	0.009 (2)	0.002 (3)
C4	0.043 (2)	0.055 (3)	0.045 (2)	−0.006 (2)	0.010 (2)	0.002 (2)
C5	0.040 (3)	0.059 (3)	0.057 (3)	−0.005 (2)	0.010 (2)	−0.003 (2)
C6	0.045 (3)	0.057 (3)	0.062 (3)	−0.004 (2)	0.010 (2)	0.002 (2)
O2	0.123 (7)	0.082 (5)	0.125 (7)	−0.002 (5)	0.063 (6)	0.020 (5)
O3	0.098 (7)	0.104 (6)	0.148 (8)	−0.010 (6)	0.068 (7)	−0.018 (6)
O4	0.072 (5)	0.074 (5)	0.107 (6)	0.006 (4)	0.018 (5)	−0.014 (4)
O5	0.166 (11)	0.162 (9)	0.137 (9)	−0.001 (9)	−0.001 (8)	−0.008 (8)

Ag—N1i	2.138 (5)	C2—H2	0.9300
Ag—N1	2.138 (5)	C3—C4	1.402 (8)
Ag—O2	2.843 (9)	C3—H3	0.9300
O1—N2	1.387 (7)	C4—C5	1.378 (7)
O1—H1o	0.8400	C4—C6	1.449 (8)
N1—C1	1.327 (7)	C5—H5	0.9300
N1—C5	1.346 (7)	C6—H6	0.9300
N2—C6	1.255 (7)	Cl—O5	1.283 (7)
C1—C2	1.374 (9)	Cl—O3	1.426 (7)
C1—H1	0.9300	Cl—O4	1.474 (6)
C2—C3	1.357 (8)	Cl—O2	1.490 (6)
N1i—Ag—N1	170.0 (2)	C5—C4—C3	117.1 (5)
N1i—Ag—O2	95.1 (3)	C5—C4—C6	118.6 (5)
N1—Ag—O2	94.2 (3)	C3—C4—C6	124.3 (5)
N2—O1—H1o	109.5	N1—C5—C4	124.0 (5)
C1—N1—C5	117.2 (5)	N1—C5—H5	118.0
C1—N1—Ag	124.1 (4)	C4—C5—H5	118.0
C5—N1—Ag	118.6 (3)	N2—C6—C4	122.0 (5)
C6—N2—O1	112.5 (5)	N2—C6—H6	119.0
N1—C1—C2	122.9 (5)	C4—C6—H6	119.0
N1—C1—H1	118.6	O5—Cl—O3	120.9 (7)
C2—C1—H1	118.6	O5—Cl—O4	114.9 (7)
C3—C2—C1	119.8 (5)	O3—Cl—O4	103.4 (5)
C3—C2—H2	120.1	O5—Cl—O2	113.4 (7)
C1—C2—H2	120.1	O3—Cl—O2	101.3 (5)
C2—C3—C4	119.1 (5)	O4—Cl—O2	100.0 (5)
C2—C3—H3	120.5	Cl—O2—Ag	117.8 (5)
C4—C3—H3	120.5
N1i—Ag—N1—C1	168.7 (5)	Ag—N1—C5—C4	178.7 (4)
O2—Ag—N1—C1	9.2 (5)	C3—C4—C5—N1	−0.4 (8)
N1i—Ag—N1—C5	−9.2 (4)	C6—C4—C5—N1	−177.8 (5)
O2—Ag—N1—C5	−168.7 (4)	O1—N2—C6—C4	−178.7 (5)
C5—N1—C1—C2	−0.7 (9)	C5—C4—C6—N2	175.0 (5)
Ag—N1—C1—C2	−178.7 (5)	C3—C4—C6—N2	−2.3 (9)
N1—C1—C2—C3	0.5 (10)	O5—Cl—O2—Ag	−57.3 (9)
C1—C2—C3—C4	−0.2 (9)	O3—Cl—O2—Ag	73.9 (7)
C2—C3—C4—C5	0.1 (8)	O4—Cl—O2—Ag	179.9 (5)
C2—C3—C4—C6	177.4 (5)	N1—Ag—O2—Cl	−93.0 (6)
C1—N1—C5—C4	0.7 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N2ii	0.84	2.07	2.821 (7)	148

Table 1

Selected bond lengths (Å)

Ag—N1	2.138 (5)
Ag—O2	2.843 (9)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N2i	0.84	2.07	2.821 (7)	148

Symmetry code: (i) .