(Nitrato-κ2O,O′)bis­[(E)-N-(pyridin-4-yl­methyl­idene-κN)hy­droxy­amine]­silver(I)

Gao, S.; Ng, S.W.

doi:10.1107/S1600536812046107

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page m1542

doi:10.1107/S1600536812046107

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(Nitrato-κ²O,O′)bis[(E)-N-(pyridin-4-ylmethylidene-κN)hydroxyamine]silver(I)

Shan Gao ^a and Seik Weng Ng ^b,^c ^*

^aKey Laboratory of Functional Inorganic Material Chemistry, Ministry of Education, Heilongjiang University, Harbin 150080, People's Republic of China, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 4 November 2012; accepted 8 November 2012; online 28 November 2012)

In the mononuclear title compound, [Ag(NO₃)(C₆H₆N₂O)₂], the Ag^I atom is located on a twofold rotation axis and the nitrate-chelated Ag^I atom is further coordinated by two aromatic N atoms of hydroxylamine ligands in a distorted tetrahedral geometry. In the crystal, the nitrate ion has 2 symmetry with the N atom and one O atom located on the twofold rotation axis, and is linked to hydroxy groups of the hydroxylamine ligands by O—H⋯O hydrogen bonds, generating a chain running along the b axis.

Related literature

For (nitrato)(picolinaldehyde oxime)silver(I), see: Abu-Youssef et al. (2010 ).

Experimental

Crystal data

[Ag(NO₃)(C₆H₆N₂O)₂]
M_r = 414.14
Orthorhombic, P c c n
a = 18.027 (3) Å
b = 4.6907 (6) Å
c = 17.7020 (19) Å
V = 1496.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.38 mm⁻¹
T = 293 K
0.20 × 0.12 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.770, T_max = 0.852
13223 measured reflections
1705 independent reflections
1038 reflections with I > 2σ(I)
R_int = 0.082

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.162
S = 1.13
1705 reflections
108 parameters
H-atom parameters constrained
Δρ_max = 0.92 e Å⁻³
Δρ_min = −0.67 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.84	1.90	2.740 (6)	173
Symmetry code: (i) $[-x+1, y+{\script{3\over 2}}, -z+{\script{1\over 2}}]$ .

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 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812046107/xu5647sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812046107/xu5647Isup2.hkl

checkCIF report

Comment top

Picolinylaldehyde oxime reacts with silver nitrate to yield a monomeric adduct in which the metal atom is N,N'-chelated by the ligand. The nitrate ion is also involved in coordination (Abu-Youssef et al., 2010). The corresponding reaction with isonicotinylaldehyde in place of picolinylaldehyde yields a bis adduct (Scheme I). The nitrate-chelated Ag^I atom in mononuclear Ag(NO₃)(C₆H₆N₂O)₂ is coordinated to the hydroxylamine through its aromatic N atom, and it exists in an approximate tetrahedral geometry (Fig. 1). The hydroxyl OH group forms a hydrogen bond with a nitrate O atom to generate a chain running along the longest axis of the orthorhombic unit cell (Table 1).

Related literature top

For (nitrato)(picolinaldehyde oxime)silver, see: Abu-Youssef et al. (2010).

Experimental top

Isonicotinaldehyde oxime was synthesized from the reaction of isonicotinaldehyde and hydroxylamine. Silver nitrate (1 mmol) dissolved in water (5 ml) was added to picolinaldehyde oxime (1 mmol) dissolved in ethanol (5 ml). The solution was filtered and set aside, away from light, for the growth of colorless crystals.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); 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); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of Ag(NO₃)(C₆H₆N₂O)₂ at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Hydrogen-bonded chain motif.

(Nitrato-κ²O,O')bis[(E)-N-(pyridin-4- ylmethylidene-κN)hydroxyamine]silver(I) top

Crystal data top

[Ag(NO₃)(C₆H₆N₂O)₂]	F(000) = 824
M_r = 414.14	D_x = 1.838 Mg m⁻³
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 4605 reflections
a = 18.027 (3) Å	θ = 3.2–27.5°
b = 4.6907 (6) Å	µ = 1.38 mm⁻¹
c = 17.7020 (19) Å	T = 293 K
V = 1496.9 (3) Å³	Prism, colorless
Z = 4	0.20 × 0.12 × 0.12 mm

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	1705 independent reflections
Radiation source: fine-focus sealed tube	1038 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.082
ω scan	θ_max = 27.5°, θ_min = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −23→23
T_min = 0.770, T_max = 0.852	k = −5→6
13223 measured reflections	l = −21→22

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.162	w = 1/[σ²(F_o²) + (0.073P)² + 1.2436P] where P = (F_o² + 2F_c²)/3
S = 1.13	(Δ/σ)_max = 0.001
1705 reflections	Δρ_max = 0.92 e Å⁻³
108 parameters	Δρ_min = −0.67 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0096 (16)

Crystal data top

[Ag(NO₃)(C₆H₆N₂O)₂]	V = 1496.9 (3) Å³
M_r = 414.14	Z = 4
Orthorhombic, Pccn	Mo Kα radiation
a = 18.027 (3) Å	µ = 1.38 mm⁻¹
b = 4.6907 (6) Å	T = 293 K
c = 17.7020 (19) Å	0.20 × 0.12 × 0.12 mm

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	1705 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1038 reflections with I > 2σ(I)
T_min = 0.770, T_max = 0.852	R_int = 0.082
13223 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.162	H-atom parameters constrained
S = 1.13	Δρ_max = 0.92 e Å⁻³
1705 reflections	Δρ_min = −0.67 e Å⁻³
108 parameters

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

	x	y	z	U_iso*/U_eq
Ag1	0.2500	0.2500	0.18639 (3)	0.0532 (4)
O1	0.5757 (2)	1.5200 (8)	0.0886 (2)	0.0584 (11)
H1	0.6143	1.5575	0.1132	0.088*
O2	0.3058 (3)	0.1732 (13)	0.3234 (2)	0.0789 (15)
O3	0.2500	0.2500	0.4306 (3)	0.093 (3)
N1	0.3325 (2)	0.5683 (9)	0.1548 (2)	0.0454 (11)
N2	0.5350 (3)	1.3109 (9)	0.1264 (2)	0.0487 (11)
N3	0.2500	0.2500	0.3606 (4)	0.067 (2)
C1	0.3371 (3)	0.6602 (14)	0.0824 (3)	0.0487 (13)
H1A	0.3067	0.5752	0.0464	0.058*
C2	0.3841 (3)	0.8714 (12)	0.0598 (2)	0.0426 (12)
H2	0.3840	0.9318	0.0098	0.051*
C3	0.4321 (2)	0.9961 (10)	0.1113 (3)	0.0397 (11)
C4	0.4286 (3)	0.9016 (12)	0.1858 (3)	0.0466 (13)
H4	0.4601	0.9782	0.2222	0.056*
C5	0.3783 (3)	0.6940 (12)	0.2050 (3)	0.0454 (13)
H5	0.3756	0.6371	0.2552	0.055*
C6	0.4830 (3)	1.2177 (11)	0.0848 (3)	0.0459 (13)
H6	0.4771	1.2919	0.0365	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0461 (5)	0.0541 (5)	0.0594 (5)	−0.0093 (3)	0.000	0.000
O1	0.051 (2)	0.064 (3)	0.060 (2)	−0.022 (2)	−0.0052 (18)	0.007 (2)
O2	0.054 (3)	0.124 (4)	0.059 (3)	0.037 (3)	0.006 (2)	0.002 (2)
O3	0.084 (6)	0.155 (10)	0.040 (3)	0.050 (5)	0.000	0.000
N1	0.038 (2)	0.047 (3)	0.051 (2)	−0.007 (2)	0.0030 (19)	−0.003 (2)
N2	0.049 (3)	0.050 (3)	0.046 (2)	−0.009 (2)	0.003 (2)	0.0004 (19)
N3	0.057 (5)	0.084 (6)	0.061 (5)	0.020 (4)	0.000	0.000
C1	0.040 (3)	0.061 (3)	0.045 (3)	0.002 (3)	−0.002 (2)	−0.005 (3)
C2	0.039 (3)	0.050 (3)	0.039 (3)	0.000 (3)	0.000 (2)	0.003 (2)
C3	0.034 (2)	0.040 (3)	0.045 (3)	0.002 (2)	0.003 (2)	0.001 (2)
C4	0.047 (3)	0.045 (3)	0.047 (3)	−0.004 (3)	−0.004 (2)	0.000 (2)
C5	0.043 (3)	0.053 (3)	0.041 (3)	−0.009 (2)	−0.001 (2)	−0.002 (2)
C6	0.046 (3)	0.051 (3)	0.041 (2)	0.002 (2)	−0.005 (2)	0.000 (2)

Geometric parameters (Å, º) top

Ag1—N1ⁱ	2.180 (4)	N3—O2ⁱ	1.256 (6)
Ag1—N1	2.180 (4)	C1—C2	1.364 (9)
Ag1—O2	2.651 (4)	C1—H1A	0.9300
Ag1—O2ⁱ	2.651 (4)	C2—C3	1.386 (7)
O1—N2	1.396 (5)	C2—H2	0.9300
O1—H1	0.8400	C3—C4	1.393 (6)
O2—N3	1.256 (6)	C3—C6	1.463 (7)
O3—N3	1.239 (9)	C4—C5	1.374 (8)
N1—C5	1.349 (6)	C4—H4	0.9300
N1—C1	1.354 (6)	C5—H5	0.9300
N2—C6	1.270 (7)	C6—H6	0.9300

N1ⁱ—Ag1—N1	150.3 (2)	C2—C1—H1A	118.4
N1ⁱ—Ag1—O2	113.62 (18)	C1—C2—C3	120.1 (4)
N1—Ag1—O2	93.94 (18)	C1—C2—H2	119.9
N1ⁱ—Ag1—O2ⁱ	93.94 (18)	C3—C2—H2	119.9
N1—Ag1—O2ⁱ	113.62 (18)	C2—C3—C4	117.4 (4)
O2—Ag1—O2ⁱ	47.57 (19)	C2—C3—C6	118.7 (4)
N2—O1—H1	109.5	C4—C3—C6	123.9 (4)
N3—O2—Ag1	97.9 (4)	C5—C4—C3	119.3 (5)
C5—N1—C1	116.5 (5)	C5—C4—H4	120.3
C5—N1—Ag1	123.2 (3)	C3—C4—H4	120.3
C1—N1—Ag1	120.2 (3)	N1—C5—C4	123.5 (5)
C6—N2—O1	110.6 (4)	N1—C5—H5	118.3
O3—N3—O2ⁱ	121.6 (4)	C4—C5—H5	118.3
O3—N3—O2	121.6 (4)	N2—C6—C3	121.4 (5)
O2ⁱ—N3—O2	116.7 (7)	N2—C6—H6	119.3
N1—C1—C2	123.2 (5)	C3—C6—H6	119.3
N1—C1—H1A	118.4

N1ⁱ—Ag1—O2—N3	−72.7 (4)	Ag1—N1—C1—C2	175.7 (4)
N1—Ag1—O2—N3	118.8 (3)	N1—C1—C2—C3	2.3 (9)
O2ⁱ—Ag1—O2—N3	0.000 (1)	C1—C2—C3—C4	−1.5 (8)
N1ⁱ—Ag1—N1—C5	−171.4 (4)	C1—C2—C3—C6	178.7 (5)
O2—Ag1—N1—C5	−12.8 (4)	C2—C3—C4—C5	−0.5 (8)
O2ⁱ—Ag1—N1—C5	32.1 (5)	C6—C3—C4—C5	179.4 (5)
N1ⁱ—Ag1—N1—C1	12.1 (4)	C1—N1—C5—C4	−1.1 (8)
O2—Ag1—N1—C1	170.6 (4)	Ag1—N1—C5—C4	−177.7 (4)
O2ⁱ—Ag1—N1—C1	−144.4 (4)	C3—C4—C5—N1	1.8 (9)
Ag1—O2—N3—O3	180.0	O1—N2—C6—C3	179.9 (4)
Ag1—O2—N3—O2ⁱ	0.000 (1)	C2—C3—C6—N2	−170.0 (5)
C5—N1—C1—C2	−1.0 (8)	C4—C3—C6—N2	10.2 (8)

Symmetry code: (i) −x+1/2, −y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱⁱ	0.84	1.90	2.740 (6)	173

Symmetry code: (ii) −x+1, y+3/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Ag(NO₃)(C₆H₆N₂O)₂]
M_r	414.14
Crystal system, space group	Orthorhombic, Pccn
Temperature (K)	293
a, b, c (Å)	18.027 (3), 4.6907 (6), 17.7020 (19)
V (Å³)	1496.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.38
Crystal size (mm)	0.20 × 0.12 × 0.12

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.770, 0.852
No. of measured, independent and observed [I > 2σ(I)] reflections	13223, 1705, 1038
R_int	0.082
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.162, 1.13
No. of reflections	1705
No. of parameters	108
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.92, −0.67

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.84	1.90	2.740 (6)	172.8

Symmetry code: (i) −x+1, y+3/2, −z+1/2.

Acknowledgements

We thank the Key Project of the Natural Science Foundation of Heilongjiang Province (No. ZD200903), the Key Project of the Education Bureau of Heilongjiang Province (Nos. 12511z023 and 2011CJHB006), the Innovation Team of the Education Bureau of Heilongjiang Province (No. 2010 t d03), Heilongjiang University (Hdtd2010–04) and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.

References

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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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