Bis[μ-(E)-N-(pyridin-3-yl-methyl-idene)hy-droxy-amine]-κ(2) N (1):N (3);κ(2) N (3):N (1)-bis-{[(E)-N-(pyridin-3-yl-methyl-idene-κN)hy-droxy-amine]-silver(I)} dinitrate.

In the centrosymmetric dinuclear title Ag(I) compound, [Ag2(C6H6N2O)4](NO3)2, the aromatic amine-coordinated Ag(I) atom is further bridged by two hydroxyl-amine mol-ecules that use aromatic and oxime N atoms for bridging, and it exists in a distorted trigonal-planar geometry. In the crystal, the nitrate anions link to the dinuclear compound mol-ecules via O-H⋯O hydrogen bonds, generating a chain running along the a-axis direction.

Related literature

For bis­(nicotinyl­aldehyde oxime)silver perchlorate, see: Xu et al. (2012 ▶) and for (nitrato)(picolinaldehyde oxime)silver, see: Abu-Youssef et al. (2010 ▶).

Experimental

Crystal data

[Ag2(C6H6N2O)4](NO3)2

M = 828.27

Triclinic,

a = 7.2913 (10) Å

b = 8.3395 (10) Å

c = 13.1415 (17) Å

α = 92.934 (4)°

β = 95.008 (4)°

γ = 111.360 (3)°

V = 738.38 (16) Å3

Z = 1

Mo Kα radiation

μ = 1.40 mm−1

T = 293 K

0.24 × 0.21 × 0.17 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.730, T max = 0.797

7293 measured reflections

3341 independent reflections

2896 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.107

S = 1.11

3341 reflections

210 parameters

H-atom parameters constrained

Δρmax = 1.71 e Å−3

Δρmin = −0.34 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 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812045898/xu5646sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812045898/xu5646Isup2.hkl

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

[Ag2(C6H6N2O)4](NO3)2	Z = 1
Mr = 828.27	F(000) = 412
Triclinic, P1	Dx = 1.863 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2913 (10) Å	Cell parameters from 6130 reflections
b = 8.3395 (10) Å	θ = 3.0–27.4°
c = 13.1415 (17) Å	µ = 1.40 mm−1
α = 92.934 (4)°	T = 293 K
β = 95.008 (4)°	Prism, colorless
γ = 111.360 (3)°	0.24 × 0.21 × 0.17 mm
V = 738.38 (16) Å3

Rigaku R-AXIS RAPID IP diffractometer	3341 independent reflections
Radiation source: fine-focus sealed tube	2896 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
ω scan	θmax = 27.4°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→9
Tmin = 0.730, Tmax = 0.797	k = −10→10
7293 measured reflections	l = −17→16

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.056P)2 + 0.3361P] where P = (Fo2 + 2Fc2)/3
3341 reflections	(Δ/σ)max = 0.001
210 parameters	Δρmax = 1.71 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

	x	y	z	Uiso*/Ueq
Ag1	0.38614 (4)	0.61092 (3)	0.314850 (18)	0.04700 (13)
O1	1.0366 (4)	0.7195 (3)	0.7651 (2)	0.0501 (6)
H1	1.0758	0.6378	0.7541	0.075*
O2	0.9485 (4)	1.1845 (3)	−0.0856 (2)	0.0522 (6)
H2	0.9451	1.2272	−0.1419	0.078*
O3	0.7359 (7)	0.5156 (5)	0.3151 (4)	0.1102 (16)
O4	1.0106 (5)	0.6444 (5)	0.2602 (3)	0.0751 (10)
O5	0.8581 (6)	0.7867 (4)	0.3354 (3)	0.0792 (10)
N1	0.4261 (4)	0.7161 (4)	0.4767 (2)	0.0393 (6)
N2	0.8633 (4)	0.6911 (4)	0.7003 (2)	0.0426 (6)
N3	0.4227 (4)	0.6552 (4)	0.1507 (2)	0.0393 (6)
N4	0.7795 (4)	1.0353 (4)	−0.0856 (2)	0.0411 (6)
N5	0.8690 (4)	0.6504 (4)	0.3059 (2)	0.0436 (7)
C1	0.2918 (5)	0.5528 (4)	0.0748 (3)	0.0420 (7)
H1A	0.1875	0.4574	0.0915	0.050*
C2	0.3047 (5)	0.5827 (4)	−0.0277 (3)	0.0438 (7)
H2A	0.2104	0.5087	−0.0783	0.053*
C3	0.4576 (5)	0.7221 (4)	−0.0537 (3)	0.0410 (7)
H3	0.4689	0.7437	−0.1220	0.049*
C4	0.5962 (5)	0.8315 (4)	0.0240 (2)	0.0354 (6)
C5	0.5728 (5)	0.7911 (4)	0.1242 (2)	0.0366 (6)
H5	0.6663	0.8621	0.1762	0.044*
C6	0.7622 (5)	0.9865 (4)	0.0046 (3)	0.0375 (7)
H6	0.8559	1.0499	0.0586	0.045*
C7	0.3097 (5)	0.7957 (4)	0.5116 (3)	0.0430 (7)
H7	0.1944	0.7853	0.4708	0.052*
C8	0.3541 (5)	0.8913 (4)	0.6046 (3)	0.0429 (7)
H8	0.2721	0.9467	0.6256	0.051*
C9	0.5228 (5)	0.9041 (4)	0.6669 (3)	0.0407 (7)
H9	0.5570	0.9704	0.7296	0.049*
C10	0.6402 (5)	0.8177 (4)	0.6350 (2)	0.0361 (6)
C11	0.5871 (5)	0.7270 (4)	0.5384 (2)	0.0369 (6)
H11	0.6675	0.6713	0.5156	0.044*
C12	0.8170 (5)	0.8228 (4)	0.6996 (2)	0.0396 (7)
H12	0.8952	0.9234	0.7401	0.048*

	U11	U22	U33	U12	U13	U23
Ag1	0.05390 (19)	0.0543 (2)	0.03057 (17)	0.01848 (14)	0.00080 (12)	0.00222 (11)
O1	0.0459 (13)	0.0570 (15)	0.0475 (15)	0.0220 (12)	−0.0050 (11)	0.0026 (11)
O2	0.0459 (13)	0.0490 (14)	0.0565 (16)	0.0103 (11)	0.0045 (12)	0.0153 (12)
O3	0.101 (3)	0.062 (2)	0.155 (5)	0.007 (2)	0.035 (3)	0.043 (3)
O4	0.0682 (19)	0.124 (3)	0.062 (2)	0.064 (2)	0.0219 (16)	0.034 (2)
O5	0.100 (3)	0.0675 (19)	0.079 (2)	0.0441 (19)	0.009 (2)	−0.0041 (16)
N1	0.0458 (14)	0.0412 (14)	0.0277 (13)	0.0131 (12)	0.0010 (11)	0.0040 (10)
N2	0.0430 (14)	0.0408 (14)	0.0401 (15)	0.0129 (12)	−0.0037 (12)	0.0043 (11)
N3	0.0400 (14)	0.0462 (15)	0.0333 (14)	0.0179 (12)	0.0039 (11)	0.0034 (11)
N4	0.0401 (14)	0.0401 (14)	0.0439 (16)	0.0154 (12)	0.0063 (12)	0.0039 (12)
N5	0.0483 (16)	0.0521 (17)	0.0383 (15)	0.0257 (15)	0.0081 (13)	0.0138 (13)
C1	0.0393 (16)	0.0407 (17)	0.0425 (18)	0.0106 (14)	0.0054 (14)	0.0021 (13)
C2	0.0442 (17)	0.0446 (17)	0.0386 (18)	0.0150 (15)	−0.0037 (14)	−0.0056 (14)
C3	0.0471 (18)	0.0475 (18)	0.0297 (15)	0.0197 (15)	0.0012 (14)	0.0024 (13)
C4	0.0349 (14)	0.0415 (16)	0.0328 (15)	0.0178 (13)	0.0035 (12)	0.0027 (12)
C5	0.0352 (15)	0.0437 (16)	0.0310 (15)	0.0163 (13)	−0.0002 (12)	−0.0023 (12)
C6	0.0367 (15)	0.0424 (16)	0.0373 (17)	0.0203 (14)	0.0013 (13)	0.0012 (13)
C7	0.0394 (16)	0.0468 (17)	0.0443 (19)	0.0166 (15)	0.0061 (14)	0.0098 (14)
C8	0.0470 (17)	0.0457 (18)	0.0413 (18)	0.0210 (15)	0.0138 (15)	0.0082 (14)
C9	0.0530 (19)	0.0390 (16)	0.0322 (16)	0.0188 (15)	0.0093 (14)	0.0022 (12)
C10	0.0424 (16)	0.0309 (14)	0.0319 (15)	0.0097 (13)	0.0039 (13)	0.0057 (11)
C11	0.0439 (16)	0.0315 (14)	0.0356 (16)	0.0141 (13)	0.0066 (13)	0.0021 (12)
C12	0.0455 (17)	0.0385 (16)	0.0315 (16)	0.0129 (14)	0.0015 (13)	−0.0022 (12)

Ag1—N1	2.212 (3)	C2—C3	1.369 (5)
Ag1—N3	2.229 (3)	C2—H2A	0.9300
Ag1—N2i	2.498 (3)	C3—C4	1.396 (5)
O1—N2	1.397 (4)	C3—H3	0.9300
O1—H1	0.8400	C4—C5	1.385 (4)
O2—N4	1.396 (4)	C4—C6	1.466 (5)
O2—H2	0.8400	C5—H5	0.9300
O3—N5	1.208 (5)	C6—H6	0.9300
O4—N5	1.255 (4)	C7—C8	1.370 (5)
O5—N5	1.214 (4)	C7—H7	0.9300
N1—C11	1.339 (4)	C8—C9	1.383 (5)
N1—C7	1.349 (5)	C8—H8	0.9300
N2—C12	1.262 (4)	C9—C10	1.381 (5)
N2—Ag1i	2.498 (3)	C9—H9	0.9300
N3—C1	1.337 (5)	C10—C11	1.392 (4)
N3—C5	1.344 (4)	C10—C12	1.466 (5)
N4—C6	1.274 (4)	C11—H11	0.9300
C1—C2	1.387 (5)	C12—H12	0.9300
C1—H1A	0.9300
N1—Ag1—N3	149.49 (11)	C5—C4—C3	117.7 (3)
N1—Ag1—N2i	107.79 (10)	C5—C4—C6	119.0 (3)
N3—Ag1—N2i	101.48 (10)	C3—C4—C6	123.3 (3)
N2—O1—H1	109.5	N3—C5—C4	123.8 (3)
N4—O2—H2	109.5	N3—C5—H5	118.1
C11—N1—C7	117.6 (3)	C4—C5—H5	118.1
C11—N1—Ag1	119.9 (2)	N4—C6—C4	120.7 (3)
C7—N1—Ag1	121.6 (2)	N4—C6—H6	119.6
C12—N2—O1	112.4 (3)	C4—C6—H6	119.6
C12—N2—Ag1i	123.3 (2)	N1—C7—C8	122.8 (3)
O1—N2—Ag1i	115.10 (18)	N1—C7—H7	118.6
C1—N3—C5	117.2 (3)	C8—C7—H7	118.6
C1—N3—Ag1	121.6 (2)	C7—C8—C9	119.0 (3)
C5—N3—Ag1	121.1 (2)	C7—C8—H8	120.5
C6—N4—O2	110.6 (3)	C9—C8—H8	120.5
O3—N5—O5	120.1 (4)	C10—C9—C8	119.5 (3)
O3—N5—O4	117.9 (4)	C10—C9—H9	120.3
O5—N5—O4	121.9 (4)	C8—C9—H9	120.3
N3—C1—C2	122.8 (3)	C9—C10—C11	117.8 (3)
N3—C1—H1A	118.6	C9—C10—C12	121.5 (3)
C2—C1—H1A	118.6	C11—C10—C12	120.6 (3)
C3—C2—C1	119.4 (3)	N1—C11—C10	123.3 (3)
C3—C2—H2A	120.3	N1—C11—H11	118.4
C1—C2—H2A	120.3	C10—C11—H11	118.4
C2—C3—C4	119.0 (3)	N2—C12—C10	120.1 (3)
C2—C3—H3	120.5	N2—C12—H12	119.9
C4—C3—H3	120.5	C10—C12—H12	119.9
N3—Ag1—N1—C11	−93.9 (3)	O2—N4—C6—C4	−179.6 (3)
N2i—Ag1—N1—C11	103.1 (2)	C5—C4—C6—N4	−174.4 (3)
N3—Ag1—N1—C7	75.2 (3)	C3—C4—C6—N4	4.9 (5)
N2i—Ag1—N1—C7	−87.8 (3)	C11—N1—C7—C8	2.6 (5)
N1—Ag1—N3—C1	−147.5 (3)	Ag1—N1—C7—C8	−166.8 (2)
N2i—Ag1—N3—C1	16.0 (3)	N1—C7—C8—C9	−1.5 (5)
N1—Ag1—N3—C5	29.4 (4)	C7—C8—C9—C10	−1.4 (5)
N2i—Ag1—N3—C5	−167.1 (2)	C8—C9—C10—C11	2.9 (4)
C5—N3—C1—C2	−0.6 (5)	C8—C9—C10—C12	−178.1 (3)
Ag1—N3—C1—C2	176.4 (3)	C7—N1—C11—C10	−0.9 (5)
N3—C1—C2—C3	0.2 (5)	Ag1—N1—C11—C10	168.7 (2)
C1—C2—C3—C4	−0.4 (5)	C9—C10—C11—N1	−1.8 (5)
C2—C3—C4—C5	0.9 (5)	C12—C10—C11—N1	179.2 (3)
C2—C3—C4—C6	−178.4 (3)	O1—N2—C12—C10	179.4 (3)
C1—N3—C5—C4	1.2 (5)	Ag1i—N2—C12—C10	−35.6 (4)
Ag1—N3—C5—C4	−175.8 (2)	C9—C10—C12—N2	144.0 (3)
C3—C4—C5—N3	−1.4 (5)	C11—C10—C12—N2	−37.1 (5)
C6—C4—C5—N3	178.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3ii	0.84	2.39	3.189 (6)	158
O1—H1···O4ii	0.84	2.20	2.925 (5)	145
O2—H2···O4iii	0.84	1.92	2.745 (4)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3i	0.84	2.39	3.189 (6)	158
O1—H1⋯O4i	0.84	2.20	2.925 (5)	145
O2—H2⋯O4ii	0.84	1.92	2.745 (4)	169

Symmetry codes: (i) ; (ii) .