catena-Poly[[silver(I)-μ-2-[(pyrazin-2-yl-κ(2)N(1):N(4))amino-meth-yl]phenol] nitrate].

The Ag(I) atom in the polycationic salt, {[Ag(C(11)H(11)N(3)O)]NO(3)}(n), shows a linear coordination [N-Ag-N = 175.0 (2)°]; the polymeric nature arises from bridging by the pyrazine portion of the ligand, resulting in chains extending parallel to [100]. The NO(3) (-) counter-ions surround the polymeric chain and inter-act only weakly with it [Ag⋯O = 2.701 (4) and 2.810 (5) Å]. Adjacent chains are linked into a three-dimensional network by O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For the structure of 2-{[(pyrazin-2-yl)amino]­meth­yl}phenol, see: Gao & Ng (2012 ▶).

Experimental

Crystal data

[Ag(C11H11N3O)]NO3

M = 371.11

Monoclinic,

a = 7.1265 (9) Å

b = 9.5249 (14) Å

c = 18.654 (2) Å

β = 97.240 (4)°

V = 1256.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.63 mm−1

T = 293 K

0.27 × 0.18 × 0.13 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.668, T max = 0.817

11969 measured reflections

2864 independent reflections

2038 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.125

S = 1.02

2864 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.64 e Å−3

Δρmin = −0.77 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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812034769/xu5602sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034769/xu5602Isup2.hkl

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

[Ag(C11H11N3O)]NO3	F(000) = 736
Mr = 371.11	Dx = 1.962 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5867 reflections
a = 7.1265 (9) Å	θ = 3.1–27.5°
b = 9.5249 (14) Å	µ = 1.63 mm−1
c = 18.654 (2) Å	T = 293 K
β = 97.240 (4)°	Prism, colorless
V = 1256.1 (3) Å3	0.27 × 0.18 × 0.13 mm
Z = 4

Rigaku R-AXIS RAPID IP diffractometer	2864 independent reflections
Radiation source: fine-focus sealed tube	2038 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
ω scan	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→8
Tmin = 0.668, Tmax = 0.817	k = −12→12
11969 measured reflections	l = −24→24

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0508P)2 + 4.1394P] where P = (Fo2 + 2Fc2)/3
2864 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.64 e Å−3
0 restraints	Δρmin = −0.77 e Å−3

	x	y	z	Uiso*/Ueq
Ag1	0.06666 (5)	0.59659 (5)	0.58246 (2)	0.05110 (18)
O1	0.3023 (5)	0.4649 (5)	0.8136 (2)	0.0571 (10)
H1	0.2582	0.5291	0.8375	0.086*
O2	−0.0170 (6)	0.6917 (5)	0.4458 (2)	0.0575 (11)
O3	0.1837 (5)	0.8322 (5)	0.4064 (2)	0.0574 (11)
O4	−0.0257 (6)	0.7272 (6)	0.3321 (2)	0.0658 (12)
N1	0.3716 (5)	0.5848 (4)	0.5842 (2)	0.0316 (8)
N2	0.7616 (5)	0.5983 (4)	0.5896 (2)	0.0361 (9)
N3	0.4029 (6)	0.4097 (5)	0.6707 (2)	0.0434 (10)
H3	0.2785	0.4081	0.6661	0.052*
N4	0.0450 (6)	0.7509 (5)	0.3943 (2)	0.0414 (10)
C1	0.4556 (6)	0.6685 (5)	0.5406 (3)	0.0352 (10)
H1A	0.3804	0.7245	0.5078	0.042*
C2	0.6473 (7)	0.6755 (5)	0.5421 (3)	0.0397 (11)
H2	0.6993	0.7341	0.5100	0.048*
C3	0.6828 (6)	0.5159 (6)	0.6338 (3)	0.0368 (11)
H3A	0.7599	0.4648	0.6683	0.044*
C4	0.4845 (6)	0.5027 (5)	0.6304 (2)	0.0328 (10)
C5	0.5036 (8)	0.3108 (6)	0.7217 (3)	0.0442 (12)
H5A	0.6001	0.2642	0.6980	0.053*
H5B	0.4151	0.2395	0.7333	0.053*
C6	0.5967 (7)	0.3745 (5)	0.7914 (3)	0.0371 (11)
C7	0.7896 (7)	0.3554 (6)	0.8134 (3)	0.0451 (12)
H7	0.8625	0.3062	0.7839	0.054*
C8	0.8733 (8)	0.4086 (6)	0.8783 (3)	0.0510 (14)
H8	1.0016	0.3941	0.8926	0.061*
C9	0.7677 (8)	0.4832 (7)	0.9221 (3)	0.0529 (14)
H9	0.8247	0.5192	0.9658	0.063*
C10	0.5791 (8)	0.5042 (6)	0.9013 (3)	0.0472 (13)
H10	0.5082	0.5552	0.9308	0.057*
C11	0.4926 (7)	0.4498 (6)	0.8363 (3)	0.0404 (11)

	U11	U22	U33	U12	U13	U23
Ag1	0.0201 (2)	0.0684 (3)	0.0657 (3)	0.00250 (18)	0.00874 (18)	0.0059 (2)
O1	0.039 (2)	0.071 (3)	0.062 (3)	0.008 (2)	0.0080 (19)	−0.008 (2)
O2	0.050 (2)	0.066 (3)	0.059 (2)	0.000 (2)	0.018 (2)	0.015 (2)
O3	0.039 (2)	0.064 (3)	0.067 (3)	−0.0142 (19)	−0.0030 (19)	0.011 (2)
O4	0.048 (2)	0.102 (4)	0.047 (2)	−0.010 (2)	0.0027 (19)	−0.012 (2)
N1	0.0186 (16)	0.038 (2)	0.038 (2)	0.0005 (15)	0.0023 (15)	0.0005 (17)
N2	0.0183 (16)	0.044 (2)	0.046 (2)	−0.0003 (16)	0.0028 (16)	0.0007 (19)
N3	0.028 (2)	0.059 (3)	0.043 (2)	−0.006 (2)	0.0052 (18)	0.010 (2)
N4	0.028 (2)	0.046 (3)	0.050 (3)	−0.0013 (18)	0.0086 (19)	−0.002 (2)
C1	0.024 (2)	0.035 (3)	0.047 (3)	0.0019 (19)	0.005 (2)	0.004 (2)
C2	0.029 (2)	0.041 (3)	0.050 (3)	−0.002 (2)	0.012 (2)	0.008 (2)
C3	0.022 (2)	0.048 (3)	0.041 (3)	0.005 (2)	0.0058 (19)	0.002 (2)
C4	0.025 (2)	0.041 (3)	0.034 (2)	−0.0041 (19)	0.0101 (18)	−0.007 (2)
C5	0.042 (3)	0.046 (3)	0.045 (3)	0.002 (2)	0.010 (2)	0.003 (2)
C6	0.038 (2)	0.036 (3)	0.039 (3)	−0.001 (2)	0.009 (2)	0.007 (2)
C7	0.038 (3)	0.047 (3)	0.051 (3)	0.005 (2)	0.013 (2)	0.014 (3)
C8	0.035 (3)	0.049 (3)	0.067 (4)	0.002 (2)	−0.002 (3)	0.014 (3)
C9	0.052 (3)	0.053 (4)	0.051 (3)	−0.008 (3)	−0.005 (3)	0.003 (3)
C10	0.052 (3)	0.046 (3)	0.044 (3)	−0.002 (3)	0.010 (3)	−0.006 (2)
C11	0.035 (2)	0.040 (3)	0.047 (3)	0.001 (2)	0.007 (2)	0.005 (2)

Ag1—N1	2.172 (4)	C1—H1A	0.9300
Ag1—N2i	2.195 (4)	C2—H2	0.9300
Ag1—O2	2.701 (4)	C3—C4	1.412 (6)
Ag1—O2ii	2.810 (5)	C3—H3A	0.9300
O1—C11	1.376 (6)	C5—C6	1.511 (7)
O1—H1	0.8400	C5—H5A	0.9700
O2—N4	1.242 (6)	C5—H5B	0.9700
O3—N4	1.254 (6)	C6—C7	1.396 (7)
O4—N4	1.225 (6)	C6—C11	1.386 (7)
N1—C1	1.333 (6)	C7—C8	1.377 (8)
N1—C4	1.352 (6)	C7—H7	0.9300
N2—C3	1.314 (6)	C8—C9	1.376 (9)
N2—C2	1.344 (6)	C8—H8	0.9300
N2—Ag1iii	2.195 (4)	C9—C10	1.366 (8)
N3—C4	1.342 (6)	C9—H9	0.9300
N3—C5	1.461 (7)	C10—C11	1.390 (8)
N3—H3	0.8800	C10—H10	0.9300
C1—C2	1.364 (6)
N1—Ag1—N2i	175.01 (15)	C4—C3—H3A	119.0
N1—Ag1—O2	97.63 (13)	N1—C4—N3	118.3 (4)
N2i—Ag1—O2	87.27 (14)	N1—C4—C3	119.3 (4)
N1—Ag1—O2ii	93.12 (13)	N3—C4—C3	122.4 (5)
N2i—Ag1—O2ii	85.21 (14)	N3—C5—C6	115.3 (4)
O2—Ag1—O2ii	98.24 (12)	N3—C5—H5A	108.5
C11—O1—H1	109.5	C6—C5—H5A	108.5
N4—O2—Ag1	145.6 (3)	N3—C5—H5B	108.5
C1—N1—C4	117.2 (4)	C6—C5—H5B	108.5
C1—N1—Ag1	119.1 (3)	H5A—C5—H5B	107.5
C4—N1—Ag1	123.6 (3)	C7—C6—C11	118.1 (5)
C3—N2—C2	117.9 (4)	C7—C6—C5	120.7 (5)
C3—N2—Ag1iii	122.6 (3)	C11—C6—C5	121.2 (5)
C2—N2—Ag1iii	119.1 (3)	C6—C7—C8	120.8 (5)
C4—N3—C5	125.3 (4)	C6—C7—H7	119.6
C4—N3—H3	117.3	C8—C7—H7	119.6
C5—N3—H3	117.3	C9—C8—C7	120.2 (5)
O4—N4—O2	120.3 (5)	C9—C8—H8	119.9
O4—N4—O3	120.3 (5)	C7—C8—H8	119.9
O2—N4—O3	119.4 (5)	C8—C9—C10	120.0 (5)
N1—C1—C2	122.9 (5)	C8—C9—H9	120.0
N1—C1—H1A	118.6	C10—C9—H9	120.0
C2—C1—H1A	118.6	C9—C10—C11	120.3 (5)
C1—C2—N2	120.6 (4)	C9—C10—H10	119.8
C1—C2—H2	119.7	C11—C10—H10	119.8
N2—C2—H2	119.7	C6—C11—C10	120.5 (5)
N2—C3—C4	121.9 (4)	C6—C11—O1	116.7 (5)
N2—C3—H3A	119.0	C10—C11—O1	122.7 (5)
N1—Ag1—O2—N4	−19.9 (6)	C5—N3—C4—N1	178.2 (5)
N2i—Ag1—O2—N4	161.0 (6)	C5—N3—C4—C3	−0.7 (8)
O2ii—Ag1—O2—N4	−114.2 (6)	N2—C3—C4—N1	−5.1 (7)
O2—Ag1—N1—C1	26.1 (4)	N2—C3—C4—N3	173.8 (5)
O2ii—Ag1—N1—C1	124.9 (4)	C4—N3—C5—C6	73.9 (6)
O2ii—Ag1—N1—C4	−59.3 (4)	N3—C5—C6—C7	−124.6 (5)
Ag1—O2—N4—O4	152.0 (5)	N3—C5—C6—C11	57.3 (6)
Ag1—O2—N4—O3	−26.1 (9)	C11—C6—C7—C8	0.7 (8)
C4—N1—C1—C2	−1.2 (7)	C5—C6—C7—C8	−177.4 (5)
Ag1—N1—C1—C2	174.9 (4)	C6—C7—C8—C9	−0.8 (8)
N1—C1—C2—N2	−1.3 (8)	C7—C8—C9—C10	0.2 (9)
C3—N2—C2—C1	0.5 (7)	C8—C9—C10—C11	0.5 (9)
Ag1iii—N2—C2—C1	173.7 (4)	C7—C6—C11—C10	−0.1 (8)
C2—N2—C3—C4	2.6 (7)	C5—C6—C11—C10	178.1 (5)
Ag1iii—N2—C3—C4	−170.3 (4)	C7—C6—C11—O1	−179.0 (5)
C1—N1—C4—N3	−174.8 (4)	C5—C6—C11—O1	−0.9 (7)
Ag1—N1—C4—N3	9.2 (6)	C9—C10—C11—C6	−0.6 (8)
C1—N1—C4—C3	4.2 (7)	C9—C10—C11—O1	178.4 (5)
Ag1—N1—C4—C3	−171.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3iv	0.84	1.96	2.795 (6)	171
N3—H3···O4ii	0.88	2.22	2.982 (6)	145

Table 1

Selected bond lengths (Å)

Ag1—N1	2.172 (4)
Ag1—N2i	2.195 (4)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3ii	0.84	1.96	2.795 (6)	171
N3—H3⋯O4iii	0.88	2.22	2.982 (6)	145

Symmetry codes: (ii) ; (iii) .