Poly[[[μ3-(E)-N-(pyridin-4-yl-methyl-idene)hy-droxy-laminato-κ(3) O:N:N'][μ2-(E)-N-(pyridin-4-yl-methyl-idene)hydroxyl-amine-κ(2) N:N'][(E)-N-(pyridin-4-yl-methyl-idene-κN)hydroxyl-amine]-disilver(I)] nitrate].

The title coordination polymer, {[Ag2(C6H5N2O)(C6H6N2O)2]NO3} n , features a deprotonated N-(pyridin-4-yl-methyl-idene)hy-droxy-laminate anion and two neutral N-(pyridin-4-yl-methyl-idene)hydroxyl-amine mol-ecules in the asymmetric unit. The anion connects three Ag(I) atoms through its O and two N-donor atoms. One neutral ligand functions in a monodentate mode; the other functions in a bridging mode, binding though its two N atoms. The coordination geometry of the two independent metal atoms is T-shaped; the manner of bridging gives rise to a layer motif parallel to (100). In the crystal, the nitrate ion is disordered over two positions in a 1:1 ratio, and is sandwiched between adjacent layers. O-H⋯O hydrogen bonding is present between nitrate ions and layers, and also between adjacent layers.

Related literature

For mononuclear (Nitrato-κ2 O,O′)bis­[(E)-N-(pyridin-4-yl­meth­yl­idene-κN)hy­droxy­amine]­silver(I), see: Gao & Ng (2012 ▶).

Experimental

Crystal data

[Ag2(C6H5N2O)(C6H6N2O)2]NO3

M = 643.13

Monoclinic,

a = 13.1628 (18) Å

b = 10.9926 (18) Å

c = 16.315 (2) Å

β = 110.412 (4)°

V = 2212.4 (6) Å3

Z = 4

Mo Kα radiation

μ = 1.82 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 = 0.712, T max = 0.811

21226 measured reflections

5047 independent reflections

3355 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.119

S = 1.07

5047 reflections

306 parameters

26 restraints

H-atom parameters constrained

Δρmax = 0.77 e Å−3

Δρmin = −0.43 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/S1600536812046090/xu5648sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046090/xu5648Isup2.hkl

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

[Ag2(C6H5N2O)(C6H6N2O)2]NO3	F(000) = 1264
Mr = 643.13	Dx = 1.931 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10662 reflections
a = 13.1628 (18) Å	θ = 3.1–27.5°
b = 10.9926 (18) Å	µ = 1.82 mm−1
c = 16.315 (2) Å	T = 293 K
β = 110.412 (4)°	Prism, colorless
V = 2212.4 (6) Å3	0.20 × 0.12 × 0.12 mm
Z = 4

Rigaku R-AXIS RAPID IP diffractometer	5047 independent reflections
Radiation source: fine-focus sealed tube	3355 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
ω scan	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −17→17
Tmin = 0.712, Tmax = 0.811	k = −14→14
21226 measured reflections	l = −19→21

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0609P)2] where P = (Fo2 + 2Fc2)/3
5047 reflections	(Δ/σ)max = 0.001
306 parameters	Δρmax = 0.77 e Å−3
26 restraints	Δρmin = −0.43 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ag1	0.82406 (3)	0.44988 (5)	0.68283 (2)	0.0906 (2)
Ag2	0.45572 (3)	0.01686 (3)	0.114909 (19)	0.06273 (15)
O1	0.6234 (2)	0.4403 (3)	0.57575 (15)	0.0523 (6)
O2	1.0680 (3)	0.1718 (4)	0.3037 (2)	0.1041 (13)
H2	1.0946	0.1023	0.3041	0.156*
O3	0.6612 (3)	0.8349 (3)	1.07189 (16)	0.0633 (8)
H3	0.6532	0.9104	1.0744	0.095*
O4	1.1249 (5)	−0.0582 (8)	0.3006 (6)	0.1012 (16)	0.50
O5	1.2395 (7)	−0.1874 (9)	0.2869 (8)	0.1012 (16)	0.50
O6	1.2906 (5)	−0.0465 (7)	0.3833 (5)	0.1012 (16)	0.50
O4'	1.1788 (14)	−0.0670 (13)	0.3637 (8)	0.187 (4)	0.50
O5'	1.2614 (15)	−0.1635 (11)	0.2915 (11)	0.187 (4)	0.50
O6'	1.2181 (13)	0.0236 (10)	0.2655 (8)	0.187 (4)	0.50
N1	0.5108 (3)	0.0936 (3)	0.24501 (19)	0.0556 (8)
N2	0.6020 (2)	0.3906 (3)	0.49497 (17)	0.0460 (7)
N3	0.8829 (3)	0.3913 (4)	0.5817 (2)	0.0707 (11)
N4	1.0390 (3)	0.1859 (5)	0.3770 (2)	0.0763 (12)
N5	0.7900 (3)	0.5396 (4)	0.7881 (2)	0.0676 (10)
N6	0.6741 (3)	0.8056 (3)	0.99397 (19)	0.0522 (8)
N7	1.2216 (8)	−0.0974 (7)	0.3251 (6)	0.0797 (19)	0.50
N7'	1.2207 (7)	−0.0713 (10)	0.3065 (6)	0.0797 (19)	0.50
C1	0.5737 (3)	0.1916 (4)	0.2613 (2)	0.0578 (10)
H1	0.5978	0.2198	0.2175	0.069*
C2	0.6052 (3)	0.2537 (4)	0.3395 (2)	0.0553 (9)
H2A	0.6491	0.3223	0.3475	0.066*
C3	0.5710 (3)	0.2131 (4)	0.4062 (2)	0.0510 (9)
C4	0.5075 (4)	0.1096 (4)	0.3898 (2)	0.0589 (10)
H4	0.4840	0.0783	0.4331	0.071*
C5	0.4786 (4)	0.0526 (4)	0.3098 (3)	0.0627 (11)
H5	0.4354	−0.0166	0.3001	0.075*
C6	0.5966 (3)	0.2758 (4)	0.4903 (2)	0.0536 (9)
H6	0.6089	0.2305	0.5410	0.064*
C7	0.9441 (4)	0.2916 (5)	0.5886 (3)	0.0783 (14)
H7	0.9633	0.2467	0.6401	0.094*
C8	0.9799 (4)	0.2525 (5)	0.5230 (3)	0.0720 (13)
H8	1.0224	0.1830	0.5305	0.086*
C9	0.9516 (3)	0.3179 (4)	0.4458 (3)	0.0614 (11)
C10	0.8877 (3)	0.4200 (5)	0.4382 (3)	0.0651 (11)
H10	0.8670	0.4666	0.3874	0.078*
C11	0.8553 (4)	0.4518 (5)	0.5069 (3)	0.0701 (13)
H11	0.8114	0.5200	0.5005	0.084*
C12	0.9898 (4)	0.2858 (5)	0.3741 (3)	0.0706 (12)
H12	0.9781	0.3383	0.3270	0.085*
C13	0.7989 (4)	0.4791 (5)	0.8613 (3)	0.0721 (13)
H13	0.8249	0.3997	0.8674	0.087*
C14	0.7717 (4)	0.5284 (4)	0.9274 (3)	0.0623 (11)
H14	0.7795	0.4827	0.9772	0.075*
C15	0.7327 (3)	0.6453 (4)	0.9210 (2)	0.0528 (9)
C16	0.7235 (3)	0.7088 (4)	0.8454 (2)	0.0642 (11)
H16	0.6980	0.7885	0.8378	0.077*
C17	0.7525 (4)	0.6524 (5)	0.7817 (3)	0.0730 (13)
H17	0.7454	0.6960	0.7311	0.088*
C18	0.7078 (3)	0.6971 (4)	0.9947 (2)	0.0563 (10)
H18	0.7171	0.6489	1.0437	0.068*

	U11	U22	U33	U12	U13	U23
Ag1	0.0834 (3)	0.1332 (5)	0.0585 (2)	0.0248 (2)	0.0289 (2)	−0.0216 (2)
Ag2	0.0788 (3)	0.0733 (3)	0.03828 (19)	−0.01131 (17)	0.02310 (17)	−0.01213 (14)
O1	0.0644 (15)	0.0577 (17)	0.0356 (13)	−0.0003 (13)	0.0187 (12)	−0.0058 (12)
O2	0.111 (3)	0.147 (4)	0.067 (2)	0.034 (3)	0.046 (2)	−0.015 (2)
O3	0.0896 (19)	0.066 (2)	0.0418 (14)	0.0126 (17)	0.0320 (14)	0.0045 (13)
O4	0.079 (3)	0.101 (4)	0.109 (3)	0.025 (2)	0.014 (3)	−0.034 (3)
O5	0.079 (3)	0.101 (4)	0.109 (3)	0.025 (2)	0.014 (3)	−0.034 (3)
O6	0.079 (3)	0.101 (4)	0.109 (3)	0.025 (2)	0.014 (3)	−0.034 (3)
O4'	0.258 (10)	0.189 (9)	0.143 (6)	0.063 (7)	0.107 (7)	0.017 (6)
O5'	0.258 (10)	0.189 (9)	0.143 (6)	0.063 (7)	0.107 (7)	0.017 (6)
O6'	0.258 (10)	0.189 (9)	0.143 (6)	0.063 (7)	0.107 (7)	0.017 (6)
N1	0.069 (2)	0.062 (2)	0.0371 (16)	−0.0044 (18)	0.0200 (15)	−0.0061 (15)
N2	0.0533 (16)	0.054 (2)	0.0300 (14)	0.0030 (15)	0.0140 (13)	−0.0019 (13)
N3	0.064 (2)	0.093 (3)	0.054 (2)	0.009 (2)	0.0206 (18)	−0.014 (2)
N4	0.072 (2)	0.105 (4)	0.055 (2)	0.009 (2)	0.0257 (19)	−0.019 (2)
N5	0.071 (2)	0.086 (3)	0.047 (2)	0.012 (2)	0.0214 (18)	−0.0107 (19)
N6	0.0588 (18)	0.061 (2)	0.0401 (16)	−0.0009 (16)	0.0212 (15)	−0.0022 (15)
N7	0.098 (3)	0.102 (5)	0.050 (4)	0.016 (3)	0.039 (3)	0.003 (3)
N7'	0.098 (3)	0.102 (5)	0.050 (4)	0.016 (3)	0.039 (3)	0.003 (3)
C1	0.076 (3)	0.061 (3)	0.042 (2)	−0.006 (2)	0.027 (2)	−0.0037 (18)
C2	0.068 (2)	0.052 (2)	0.046 (2)	−0.006 (2)	0.0211 (19)	−0.0028 (18)
C3	0.065 (2)	0.049 (2)	0.0373 (17)	0.0062 (19)	0.0171 (17)	−0.0002 (16)
C4	0.082 (3)	0.058 (3)	0.042 (2)	−0.005 (2)	0.027 (2)	0.0007 (18)
C5	0.085 (3)	0.058 (3)	0.051 (2)	−0.014 (2)	0.030 (2)	−0.009 (2)
C6	0.072 (2)	0.053 (3)	0.0359 (18)	0.007 (2)	0.0188 (18)	0.0028 (17)
C7	0.083 (3)	0.098 (4)	0.053 (2)	0.020 (3)	0.023 (2)	−0.002 (3)
C8	0.068 (3)	0.088 (4)	0.059 (2)	0.015 (2)	0.022 (2)	−0.008 (3)
C9	0.048 (2)	0.081 (3)	0.055 (2)	−0.002 (2)	0.0171 (19)	−0.012 (2)
C10	0.057 (2)	0.083 (3)	0.057 (2)	0.007 (2)	0.022 (2)	−0.003 (2)
C11	0.057 (2)	0.078 (3)	0.072 (3)	0.010 (2)	0.018 (2)	−0.014 (3)
C12	0.068 (3)	0.088 (4)	0.057 (3)	0.008 (3)	0.023 (2)	−0.007 (2)
C13	0.077 (3)	0.068 (3)	0.072 (3)	0.011 (2)	0.027 (3)	−0.011 (2)
C14	0.080 (3)	0.060 (3)	0.052 (2)	0.003 (2)	0.028 (2)	0.004 (2)
C15	0.050 (2)	0.062 (3)	0.046 (2)	−0.0010 (18)	0.0171 (17)	−0.0025 (19)
C16	0.074 (3)	0.073 (3)	0.046 (2)	0.016 (2)	0.021 (2)	0.002 (2)
C17	0.085 (3)	0.092 (4)	0.043 (2)	0.015 (3)	0.023 (2)	0.002 (2)
C18	0.069 (2)	0.061 (3)	0.042 (2)	0.002 (2)	0.0229 (19)	0.0016 (18)

Ag1—O1	2.612 (3)	C1—H1	0.9300
Ag1—N3	2.151 (3)	C2—C3	1.389 (5)
Ag1—N5	2.158 (3)	C2—H2A	0.9300
Ag2—O1i	2.546 (2)	C3—C4	1.382 (6)
Ag2—N1	2.161 (3)	C3—C6	1.466 (5)
Ag2—N2ii	2.183 (3)	C4—C5	1.377 (5)
O1—N2	1.362 (3)	C4—H4	0.9300
O1—Ag2iii	2.546 (2)	C5—H5	0.9300
O2—N4	1.387 (4)	C6—H6	0.9300
O2—H2	0.8400	C7—C8	1.381 (6)
O3—N6	1.378 (4)	C7—H7	0.9300
O3—H3	0.8400	C8—C9	1.383 (6)
O4—N7	1.270 (9)	C8—H8	0.9300
O5—N7	1.234 (6)	C9—C10	1.381 (6)
O6—N7	1.199 (11)	C9—C12	1.469 (6)
O4'—N7'	1.239 (7)	C10—C11	1.377 (6)
O5'—N7'	1.211 (8)	C10—H10	0.9300
O6'—N7'	1.234 (8)	C11—H11	0.9300
N1—C1	1.327 (5)	C12—H12	0.9300
N1—C5	1.346 (5)	C13—C14	1.362 (6)
N2—C6	1.264 (5)	C13—H13	0.9300
N2—Ag2iv	2.183 (3)	C14—C15	1.374 (6)
N3—C11	1.324 (6)	C14—H14	0.9300
N3—C7	1.342 (6)	C15—C16	1.386 (5)
N4—C12	1.267 (6)	C15—C18	1.467 (5)
N5—C17	1.325 (6)	C16—C17	1.374 (6)
N5—C13	1.337 (6)	C16—H16	0.9300
N6—C18	1.271 (5)	C17—H17	0.9300
C1—C2	1.378 (5)	C18—H18	0.9300
N3—Ag1—N5	167.71 (16)	N1—C5—C4	122.3 (4)
N3—Ag1—O1	91.45 (11)	N1—C5—H5	118.9
N5—Ag1—O1	96.21 (12)	C4—C5—H5	118.9
N1—Ag2—N2ii	162.98 (12)	N2—C6—C3	121.0 (3)
N1—Ag2—O1i	98.67 (10)	N2—C6—H6	119.5
N2ii—Ag2—O1i	89.75 (9)	C3—C6—H6	119.5
N2—O1—Ag2iii	114.36 (19)	N3—C7—C8	123.1 (5)
N2—O1—Ag1	118.84 (18)	N3—C7—H7	118.5
Ag2iii—O1—Ag1	125.99 (9)	C8—C7—H7	118.5
N4—O2—H2	109.5	C7—C8—C9	119.2 (5)
N6—O3—H3	109.5	C7—C8—H8	120.4
C1—N1—C5	117.4 (3)	C9—C8—H8	120.4
C1—N1—Ag2	119.0 (2)	C10—C9—C8	117.8 (4)
C5—N1—Ag2	123.4 (3)	C10—C9—C12	119.4 (4)
C6—N2—O1	116.5 (3)	C8—C9—C12	122.8 (4)
C6—N2—Ag2iv	126.0 (3)	C11—C10—C9	119.0 (4)
O1—N2—Ag2iv	115.8 (2)	C11—C10—H10	120.5
C11—N3—C7	116.9 (4)	C9—C10—H10	120.5
C11—N3—Ag1	120.0 (3)	N3—C11—C10	124.0 (4)
C7—N3—Ag1	123.1 (3)	N3—C11—H11	118.0
C12—N4—O2	110.8 (4)	C10—C11—H11	118.0
C17—N5—C13	116.7 (4)	N4—C12—C9	119.4 (5)
C17—N5—Ag1	122.7 (3)	N4—C12—H12	120.3
C13—N5—Ag1	120.4 (3)	C9—C12—H12	120.3
C18—N6—O3	111.4 (3)	N5—C13—C14	123.0 (5)
O6—N7—O5	123.3 (8)	N5—C13—H13	118.5
O6—N7—O4	119.3 (7)	C14—C13—H13	118.5
O5—N7—O4	117.4 (9)	C13—C14—C15	120.4 (4)
O5'—N7'—O6'	121.9 (8)	C13—C14—H14	119.8
O5'—N7'—O4'	122.0 (9)	C15—C14—H14	119.8
O6'—N7'—O4'	116.2 (8)	C14—C15—C16	117.0 (4)
N1—C1—C2	123.6 (3)	C14—C15—C18	119.0 (4)
N1—C1—H1	118.2	C16—C15—C18	124.0 (4)
C2—C1—H1	118.2	C17—C16—C15	119.0 (4)
C1—C2—C3	119.4 (4)	C17—C16—H16	120.5
C1—C2—H2A	120.3	C15—C16—H16	120.5
C3—C2—H2A	120.3	N5—C17—C16	123.9 (4)
C4—C3—C2	117.0 (3)	N5—C17—H17	118.1
C4—C3—C6	119.6 (3)	C16—C17—H17	118.1
C2—C3—C6	123.4 (4)	N6—C18—C15	122.2 (4)
C5—C4—C3	120.4 (3)	N6—C18—H18	118.9
C5—C4—H4	119.8	C15—C18—H18	118.9
C3—C4—H4	119.8
N3—Ag1—O1—N2	8.3 (3)	O1—N2—C6—C3	178.3 (3)
N5—Ag1—O1—N2	178.7 (2)	Ag2iv—N2—C6—C3	13.6 (5)
N3—Ag1—O1—Ag2iii	177.47 (17)	C4—C3—C6—N2	−143.2 (4)
N5—Ag1—O1—Ag2iii	−12.15 (17)	C2—C3—C6—N2	35.2 (6)
N2ii—Ag2—N1—C1	153.9 (4)	C11—N3—C7—C8	1.2 (8)
O1i—Ag2—N1—C1	35.0 (3)	Ag1—N3—C7—C8	178.5 (4)
N2ii—Ag2—N1—C5	−31.0 (6)	N3—C7—C8—C9	−0.3 (8)
O1i—Ag2—N1—C5	−149.9 (3)	C7—C8—C9—C10	−0.3 (7)
Ag2iii—O1—N2—C6	−88.6 (3)	C7—C8—C9—C12	177.4 (5)
Ag1—O1—N2—C6	81.8 (3)	C8—C9—C10—C11	0.0 (7)
Ag2iii—O1—N2—Ag2iv	77.7 (2)	C12—C9—C10—C11	−177.8 (4)
Ag1—O1—N2—Ag2iv	−111.96 (18)	C7—N3—C11—C10	−1.6 (7)
N5—Ag1—N3—C11	−73.7 (8)	Ag1—N3—C11—C10	−179.0 (4)
O1—Ag1—N3—C11	55.0 (4)	C9—C10—C11—N3	1.1 (7)
N5—Ag1—N3—C7	109.0 (8)	O2—N4—C12—C9	179.7 (4)
O1—Ag1—N3—C7	−122.3 (4)	C10—C9—C12—N4	−172.9 (4)
N3—Ag1—N5—C17	61.9 (9)	C8—C9—C12—N4	9.5 (7)
O1—Ag1—N5—C17	−66.4 (4)	C17—N5—C13—C14	−0.1 (7)
N3—Ag1—N5—C13	−122.9 (7)	Ag1—N5—C13—C14	−175.6 (4)
O1—Ag1—N5—C13	108.8 (4)	N5—C13—C14—C15	0.2 (8)
C5—N1—C1—C2	−1.4 (6)	C13—C14—C15—C16	−0.4 (7)
Ag2—N1—C1—C2	174.0 (3)	C13—C14—C15—C18	−177.8 (4)
N1—C1—C2—C3	0.4 (7)	C14—C15—C16—C17	0.5 (6)
C1—C2—C3—C4	1.0 (6)	C18—C15—C16—C17	177.8 (4)
C1—C2—C3—C6	−177.4 (4)	C13—N5—C17—C16	0.2 (7)
C2—C3—C4—C5	−1.4 (6)	Ag1—N5—C17—C16	175.6 (4)
C6—C3—C4—C5	177.1 (4)	C15—C16—C17—N5	−0.4 (8)
C1—N1—C5—C4	0.9 (7)	O3—N6—C18—C15	−177.3 (3)
Ag2—N1—C5—C4	−174.2 (3)	C14—C15—C18—N6	178.2 (4)
C3—C4—C5—N1	0.4 (7)	C16—C15—C18—N6	1.0 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O4	0.84	1.81	2.642 (9)	169
O2—H2···O4′	0.84	2.21	2.997 (14)	156
O3—H3···O1v	0.84	1.69	2.527 (4)	174

Table 1

Selected bond lengths (Å)

Ag1—O1	2.612 (3)
Ag1—N3	2.151 (3)
Ag1—N5	2.158 (3)
Ag2—O1i	2.546 (2)
Ag2—N1	2.161 (3)
Ag2—N2ii	2.183 (3)

Symmetry codes: (i) ; (ii) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O4	0.84	1.81	2.642 (9)	169
O2—H2⋯O4′	0.84	2.21	2.997 (14)	156
O3—H3⋯O1iii	0.84	1.69	2.527 (4)	174

Symmetry code: (iii) .