catena-Poly[[silver(I)-μ-[N-(4-pyridyl­meth­yl)pyridine-4-carboxamide-κ2N:N′]] nitrate monohydrate]

Ma, Y.-T.; Sun, B.-W.; Ng, S.W.

doi:10.1107/S1600536807049082

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page m470

doi:10.1107/S1600536807049082

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catena-Poly[[silver(I)-μ-[N-(4-pyridylmethyl)pyridine-4-carboxamide-κ²N:N′]] nitrate monohydrate]

Yu-Tao Ma,^a Bai-Wang Sun ^a ^* and Seik Weng Ng ^b

^aOrdered Matter Science Research Center, Department of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: chmsunbw@seu.edu.cn

(Received 26 September 2007; accepted 6 October 2007; online 13 February 2008)

The title coordination polymer, {[Ag(C₁₂H₁₁N₃O)]NO₃·H₂O}_n, has a polycationic chain motif in which the Ag atom is bridged by the heterocyclic ligand; the Ag atom shows linear coordination. If the two long Ag⋯O_nitrate interactions [2.794 (6) and 2.867 (5) Å] are regarded as bonds, the compound adopts a three-dimensional network structure. The water molecule consolidates the network structure by forming hydrogen bonds, one to the polycationic chain and one to the nitrate anion.

Related literature

For the structure of the hydrated disilver oxalate adduct of the heterocyclic ligand, see Tong et al. (2002 ).

Experimental

Crystal data

[Ag(C₁₂H₁₁N₃O)]NO₃·H₂O
M_r = 401.13
Orthorhombic, P b c a
a = 12.912 (7) Å
b = 9.021 (5) Å
c = 24.52 (1) Å
V = 2856 (3) Å³
Z = 8
Mo Kα radiation
μ = 1.45 mm⁻¹
T = 295 (2) K
0.6 × 0.4 × 0.2 mm

Data collection

Rigaku Mercury diffractometer
Absorption correction: multi-scan (Jacobson, 1998 ) T_min = 0.50, T_max = 0.75
25888 measured reflections
3249 independent reflections
2433 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.141
S = 1.06
3249 reflections
211 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.91 e Å⁻³
Δρ_min = −0.75 e Å⁻³

Table 1
Selected bond lengths (Å)

Ag1—N3ⁱ	2.162 (4)
Ag1—N1	2.170 (4)
Ag1—O2	2.803 (6)
Ag1—O3ⁱⁱ	2.874 (6)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1W	0.86 (4)	2.04 (2)	2.827 (6)	154 (5)
O1W—H1W1⋯O1ⁱⁱⁱ	0.85 (4)	2.05 (3)	2.831 (5)	154 (7)
O1W—H1W2⋯O4^iv	0.85 (4)	2.09 (4)	2.888 (7)	157 (9)
Symmetry codes: (iii) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (iv) -x+1, -y+1, -z.

Data collection: CrystalClear (Rigaku/MSC, 2005 ); cell refinement: CrystalClear ; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807049082/bg2109sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807049082/bg2109Isup2.hkl

checkCIF report

Comment top

The 4-C₅H₄N–CH₂–NH–C(O)–4-C₅H₄N ligand is a spacer heterocycle that should function like 4,4'-bipyridine, which forms numerous coordination polymers, but should be flexible. There is, however, only one crystal structure report of an adduct, a hydrated disilver oxalate adduct (Tong et al., 2002). The title silver nitrate adduct has the metal in a linear enviroment, but the N–Ag–N skeleton that gives rise to a chain structure is distorted by the presence of two Ag···O_nitrate interactions. If these are regarded as formal bonds, the compound adopts a three-dimensional network structure.

Related literature top

For the structure of the hydrated disilver oxalate adduct of the heterocyclic ligand, see Tong et al. (2002).

Experimental top

An aqueous solution (5 ml) of silver nitrate (1.0 mmol) was layed over a methanol (5 ml) solution of N-(4-pyridylmethyl)-4-pyridinecarboxamide (1.0 mmol) in a thin tube. The tube was placed vertically and kept away from light. Colorless crystals were obtained after two weeks. These were washed with methanol and collected in 50% yield. CH&N elemental analysis. Found: C 35.88, H 3.53, N 13.76%; calc. for C₁₂H₁₃AgN₄O₅: C 35.93, H 3.27, N 13.96%.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top

Fig. 1. A portion of the chain structure. Ellipsoids are drawn at the 50% probability level, and H atoms of spheres of arbitry radius. The red dashed lines denote the long Ag···O bonds and the dashed cyan line denotes the hydrogen bond. Symmetry codes (i) = 1/2 - x, 1 - y, z - 1/2; (ii) x - 1/2, 3/2 - y, -z.

catena-Poly[[silver(I)-µ-[N-(4-pyridylmethyl)pyridine-4- carboxamide-κ²N:N']] nitrate monohydrate] top

Crystal data top

[Ag(C₁₂H₁₁N₃O)]NO₃·H₂O	F(000) = 1600
M_r = 401.13	D_x = 1.879 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5655 reflections
a = 12.912 (7) Å	θ = 3.2–27.5°
b = 9.021 (5) Å	µ = 1.45 mm⁻¹
c = 24.52 (1) Å	T = 295 K
V = 2856 (3) Å³	Column, colourless
Z = 8	0.6 × 0.4 × 0.2 mm

Data collection top

Rigaku Mercury diffractometer	3249 independent reflections
Radiation source: medium-focus sealed tube	2433 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
ω scans	θ_max = 27.5°, θ_min = 3.2°
Absorption correction: multi-scan (Jacobson, 1998)	h = −16→16
T_min = 0.50, T_max = 0.75	k = −11→11
25888 measured reflections	l = −30→31

Refinement top

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0589P)² + 5.5451P] where P = (F_o² + 2F_c²)/3
3249 reflections	(Δ/σ)_max = 0.001
211 parameters	Δρ_max = 0.91 e Å⁻³
3 restraints	Δρ_min = −0.75 e Å⁻³

Crystal data top

[Ag(C₁₂H₁₁N₃O)]NO₃·H₂O	V = 2856 (3) Å³
M_r = 401.13	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 12.912 (7) Å	µ = 1.45 mm⁻¹
b = 9.021 (5) Å	T = 295 K
c = 24.52 (1) Å	0.6 × 0.4 × 0.2 mm

Data collection top

Rigaku Mercury diffractometer	3249 independent reflections
Absorption correction: multi-scan (Jacobson, 1998)	2433 reflections with I > 2σ(I)
T_min = 0.50, T_max = 0.75	R_int = 0.047
25888 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	3 restraints
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.91 e Å⁻³
3249 reflections	Δρ_min = −0.75 e Å⁻³
211 parameters

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

	x	y	z	U_iso*/U_eq
Ag1	0.16581 (3)	0.61149 (5)	0.002207 (15)	0.05996 (18)
O1	0.1859 (3)	0.1438 (4)	0.23653 (13)	0.0598 (9)
O2	0.3756 (4)	0.6914 (6)	0.00374 (16)	0.0905 (14)
O3	0.5035 (4)	0.7095 (7)	−0.0481 (2)	0.1077 (17)
O4	0.3682 (5)	0.8329 (7)	−0.0644 (2)	0.118 (2)
O1W	0.5539 (3)	0.2042 (5)	0.17401 (17)	0.0660 (10)
H1W1	0.608 (3)	0.189 (8)	0.193 (2)	0.10 (2)*
H1W2	0.562 (8)	0.176 (10)	0.1412 (13)	0.15 (4)*
N1	0.1990 (3)	0.4795 (4)	0.07408 (14)	0.0448 (8)
N2	0.3572 (3)	0.1578 (4)	0.22161 (14)	0.0458 (9)
H2N	0.408 (3)	0.198 (5)	0.2048 (19)	0.061 (16)*
N3	0.3656 (3)	0.2837 (4)	0.42466 (15)	0.0470 (9)
N4	0.4163 (3)	0.7500 (4)	−0.03557 (16)	0.0469 (9)
C1	0.1231 (4)	0.4240 (6)	0.1046 (2)	0.0567 (12)
H1	0.0551	0.4506	0.0967	0.068*
C2	0.1412 (4)	0.3281 (6)	0.14763 (19)	0.0528 (12)
H2	0.0859	0.2895	0.1674	0.063*
C3	0.2413 (3)	0.2900 (4)	0.16112 (14)	0.0377 (9)
C4	0.3201 (4)	0.3498 (6)	0.1298 (2)	0.0524 (12)
H4	0.3890	0.3279	0.1376	0.063*
C5	0.2952 (4)	0.4425 (6)	0.08692 (19)	0.0513 (11)
H5	0.3489	0.4809	0.0659	0.062*
C6	0.2592 (4)	0.1894 (5)	0.20953 (15)	0.0417 (9)
C7	0.3844 (4)	0.0665 (5)	0.26853 (17)	0.0487 (11)
H7A	0.4547	0.0307	0.2639	0.058*
H7B	0.3390	−0.0191	0.2694	0.058*
C8	0.3770 (3)	0.1465 (4)	0.32274 (16)	0.0379 (9)
C9	0.3479 (4)	0.2929 (5)	0.32757 (19)	0.0474 (11)
H9A	0.3325	0.3486	0.2967	0.057*
C10	0.3418 (4)	0.3559 (5)	0.3786 (2)	0.0515 (12)
H10	0.3201	0.4540	0.3812	0.062*
C11	0.3960 (4)	0.1419 (5)	0.41994 (18)	0.0514 (11)
H11	0.4134	0.0895	0.4513	0.062*
C12	0.4021 (4)	0.0715 (5)	0.37027 (17)	0.0482 (11)
H12	0.4233	−0.0270	0.3686	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0659 (3)	0.0671 (3)	0.0469 (3)	0.00106 (19)	−0.01097 (16)	0.01944 (19)
O1	0.065 (2)	0.074 (2)	0.0410 (18)	−0.0126 (18)	0.0093 (16)	0.0097 (17)
O2	0.111 (4)	0.103 (4)	0.058 (3)	−0.013 (3)	0.013 (2)	0.026 (2)
O3	0.076 (3)	0.171 (5)	0.076 (3)	0.009 (3)	0.003 (2)	−0.016 (3)
O4	0.130 (4)	0.135 (5)	0.089 (4)	0.049 (4)	0.001 (3)	0.050 (3)
O1W	0.056 (2)	0.087 (3)	0.055 (2)	0.005 (2)	−0.0059 (19)	0.011 (2)
N1	0.052 (2)	0.048 (2)	0.0343 (18)	0.0005 (18)	−0.0060 (16)	0.0031 (16)
N2	0.058 (2)	0.047 (2)	0.0318 (18)	0.0024 (19)	0.0050 (17)	0.0092 (16)
N3	0.053 (2)	0.049 (2)	0.0394 (19)	−0.0026 (18)	−0.0003 (17)	−0.0094 (17)
N4	0.053 (2)	0.048 (2)	0.041 (2)	−0.0017 (19)	0.0040 (18)	0.0014 (17)
C1	0.047 (3)	0.071 (3)	0.052 (3)	0.001 (2)	−0.008 (2)	0.014 (2)
C2	0.046 (2)	0.071 (3)	0.041 (2)	−0.011 (2)	−0.0001 (19)	0.006 (2)
C3	0.049 (2)	0.037 (2)	0.0265 (17)	−0.0034 (19)	0.0008 (17)	−0.0015 (15)
C4	0.043 (2)	0.063 (3)	0.051 (3)	0.007 (2)	0.005 (2)	0.018 (2)
C5	0.045 (2)	0.059 (3)	0.049 (3)	0.005 (2)	0.007 (2)	0.022 (2)
C6	0.056 (3)	0.043 (2)	0.0255 (18)	−0.004 (2)	0.0057 (18)	−0.0009 (16)
C7	0.071 (3)	0.043 (2)	0.032 (2)	0.008 (2)	−0.001 (2)	0.0033 (18)
C8	0.043 (2)	0.037 (2)	0.0333 (19)	−0.0026 (18)	−0.0003 (17)	−0.0010 (16)
C9	0.057 (3)	0.041 (2)	0.044 (2)	0.005 (2)	−0.009 (2)	−0.0001 (19)
C10	0.057 (3)	0.043 (2)	0.054 (3)	0.006 (2)	−0.006 (2)	−0.009 (2)
C11	0.073 (3)	0.046 (3)	0.035 (2)	0.001 (2)	−0.005 (2)	−0.0004 (19)
C12	0.069 (3)	0.037 (2)	0.039 (2)	0.004 (2)	0.002 (2)	0.0023 (18)

Geometric parameters (Å, º) top

Ag1—N3ⁱ	2.162 (4)	C2—C3	1.377 (6)
Ag1—N1	2.170 (4)	C2—H2	0.9300
Ag1—O2	2.803 (6)	C3—C4	1.385 (6)
Ag1—O3ⁱⁱ	2.874 (6)	C3—C6	1.512 (5)
O1—C6	1.226 (5)	C4—C5	1.381 (6)
O2—N4	1.219 (5)	C4—H4	0.9300
O3—N4	1.223 (6)	C5—H5	0.9300
O4—N4	1.202 (6)	C7—C8	1.516 (6)
O1W—H1W1	0.85 (4)	C7—H7A	0.9700
O1W—H1W2	0.85 (4)	C7—H7B	0.9700
N1—C5	1.325 (6)	C8—C9	1.378 (6)
N1—C1	1.331 (6)	C8—C12	1.386 (6)
N2—C6	1.330 (6)	C9—C10	1.377 (6)
N2—C7	1.458 (5)	C9—H9A	0.9300
N2—H2N	0.86 (4)	C10—H10	0.9300
N3—C10	1.340 (6)	C11—C12	1.376 (6)
N3—C11	1.343 (6)	C11—H11	0.9300
C1—C2	1.385 (7)	C12—H12	0.9300
C1—H1	0.9300

N3ⁱ—Ag1—N1	172.52 (14)	C5—C4—H4	120.4
N3ⁱ—Ag1—O2	94.61 (13)	C3—C4—H4	120.4
N1—Ag1—O2	86.53 (14)	N1—C5—C4	123.5 (4)
N3ⁱ—Ag1—O3ⁱⁱ	87.80 (15)	N1—C5—H5	118.3
N1—Ag1—O3ⁱⁱ	97.73 (15)	C4—C5—H5	118.3
O2—Ag1—O3ⁱⁱ	123.69 (16)	O1—C6—N2	122.8 (4)
N4—O2—Ag1	121.2 (4)	O1—C6—C3	120.5 (4)
H1W1—O1W—H1W2	111 (8)	N2—C6—C3	116.7 (4)
C5—N1—C1	117.5 (4)	N2—C7—C8	114.0 (4)
C5—N1—Ag1	121.1 (3)	N2—C7—H7A	108.7
C1—N1—Ag1	121.2 (3)	C8—C7—H7A	108.7
C6—N2—C7	121.8 (4)	N2—C7—H7B	108.7
C6—N2—H2N	122 (4)	C8—C7—H7B	108.7
C7—N2—H2N	116 (4)	H7A—C7—H7B	107.6
C10—N3—C11	117.2 (4)	C9—C8—C12	117.4 (4)
C10—N3—Ag1ⁱⁱⁱ	119.1 (3)	C9—C8—C7	123.3 (4)
C11—N3—Ag1ⁱⁱⁱ	123.2 (3)	C12—C8—C7	119.3 (4)
O4—N4—O2	120.8 (5)	C10—C9—C8	119.3 (4)
O4—N4—O3	120.9 (5)	C10—C9—H9A	120.4
O2—N4—O3	117.8 (5)	C8—C9—H9A	120.4
N1—C1—C2	122.6 (5)	N3—C10—C9	123.5 (4)
N1—C1—H1	118.7	N3—C10—H10	118.2
C2—C1—H1	118.7	C9—C10—H10	118.2
C3—C2—C1	119.8 (4)	N3—C11—C12	122.2 (4)
C3—C2—H2	120.1	N3—C11—H11	118.9
C1—C2—H2	120.1	C12—C11—H11	118.9
C2—C3—C4	117.4 (4)	C11—C12—C8	120.3 (4)
C2—C3—C6	118.8 (4)	C11—C12—H12	119.8
C4—C3—C6	123.8 (4)	C8—C12—H12	119.8
C5—C4—C3	119.1 (4)

N3ⁱ—Ag1—O2—N4	−7.1 (5)	C7—N2—C6—O1	−0.4 (7)
N1—Ag1—O2—N4	165.5 (5)	C7—N2—C6—C3	177.7 (4)
O3ⁱⁱ—Ag1—O2—N4	−97.5 (4)	C2—C3—C6—O1	−0.7 (6)
O2—Ag1—N1—C5	−17.8 (4)	C4—C3—C6—O1	177.8 (4)
O3ⁱⁱ—Ag1—N1—C5	−141.4 (4)	C2—C3—C6—N2	−178.8 (4)
O2—Ag1—N1—C1	167.1 (4)	C4—C3—C6—N2	−0.3 (6)
O3ⁱⁱ—Ag1—N1—C1	43.5 (4)	C6—N2—C7—C8	−76.5 (6)
Ag1—O2—N4—O4	33.5 (7)	N2—C7—C8—C9	−0.5 (7)
Ag1—O2—N4—O3	−138.7 (4)	N2—C7—C8—C12	−179.3 (4)
C5—N1—C1—C2	−1.5 (8)	C12—C8—C9—C10	−2.1 (7)
Ag1—N1—C1—C2	173.8 (4)	C7—C8—C9—C10	179.1 (4)
N1—C1—C2—C3	1.7 (8)	C11—N3—C10—C9	−0.6 (7)
C1—C2—C3—C4	−0.7 (7)	Ag1ⁱⁱⁱ—N3—C10—C9	−172.5 (4)
C1—C2—C3—C6	177.9 (4)	C8—C9—C10—N3	1.9 (7)
C2—C3—C4—C5	−0.5 (7)	C10—N3—C11—C12	−0.5 (7)
C6—C3—C4—C5	−179.0 (4)	Ag1ⁱⁱⁱ—N3—C11—C12	171.1 (4)
C1—N1—C5—C4	0.2 (8)	N3—C11—C12—C8	0.2 (8)
Ag1—N1—C5—C4	−175.1 (4)	C9—C8—C12—C11	1.1 (7)
C3—C4—C5—N1	0.8 (8)	C7—C8—C12—C11	180.0 (5)

Symmetry codes: (i) −x+1/2, −y+1, z−1/2; (ii) x−1/2, −y+3/2, −z; (iii) −x+1/2, −y+1, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1W	0.86 (4)	2.04 (2)	2.827 (6)	154 (5)
O1W—H1W1···O1^iv	0.85 (4)	2.05 (3)	2.831 (5)	154 (7)
O1W—H1W2···O4^v	0.85 (4)	2.09 (4)	2.888 (7)	157 (9)

Symmetry codes: (iv) x+1/2, y, −z+1/2; (v) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Ag(C₁₂H₁₁N₃O)]NO₃·H₂O
M_r	401.13
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	295
a, b, c (Å)	12.912 (7), 9.021 (5), 24.52 (1)
V (Å³)	2856 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.45
Crystal size (mm)	0.6 × 0.4 × 0.2

Data collection
Diffractometer	Rigaku Mercury diffractometer
Absorption correction	Multi-scan (Jacobson, 1998)
T_min, T_max	0.50, 0.75
No. of measured, independent and observed [I > 2σ(I)] reflections	25888, 3249, 2433
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.141, 1.06
No. of reflections	3249
No. of parameters	211
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.91, −0.75

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2007).

Selected bond lengths (Å) top

Ag1—N3ⁱ	2.162 (4)	Ag1—O2	2.803 (6)
Ag1—N1	2.170 (4)	Ag1—O3ⁱⁱ	2.874 (6)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1W	0.86 (4)	2.04 (2)	2.827 (6)	154 (5)
O1W—H1W1···O1ⁱⁱⁱ	0.85 (4)	2.05 (3)	2.831 (5)	154 (7)
O1W—H1W2···O4^iv	0.85 (4)	2.09 (4)	2.888 (7)	157 (9)

Symmetry codes: (iii) x+1/2, y, −z+1/2; (iv) −x+1, −y+1, −z.

Acknowledgements

The authors thank Southeast University, China, and the University of Malaya for supporting this study.

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