Crystal structure of catena-poly[[silver(I)-{μ-2,6-bis­[(1H-pyrazol-1-yl)meth­yl]pyridine-κ3N1,N2:N2′}] nitrate]

Kim, D.; Kang, S.K.

doi:10.1107/S2056989015004120

metal-organic compounds

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Volume 71| Part 4| April 2015| Pages m79-m80

doi:10.1107/S2056989015004120

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Crystal structure of catena-poly[[silver(I)-{μ-2,6-bis[(1H-pyrazol-1-yl)methyl]pyridine-κ³N¹,N²:N^2′}] nitrate]

Daeyoung Kim ^a and Sung Kwon Kang ^a ^*

^aDepartment of Chemistry, Chungnam National University, Daejeon 305-764, Republic of Korea
^*Correspondence e-mail: skkang@cnu.ac.kr

Edited by O. Blacque, University of Zürich, Switzerland (Received 6 February 2015; accepted 26 February 2015; online 7 March 2015)

In the title complex, {[Ag(C₁₃H₁₃N₅)]NO₃}_n, the Ag^I atom is coordinated by three N atoms from two bidentate/monodentate pyrazolylpyridyl ligands to form a distorted trigonal–planar geometry [range of angles: 83.34 (6) (chelate ring) to 139.15 (7) °]. The chelate ring has a distorted boat conformation. The dihedral angle between the pyridyl ring and the coordinating pyrazolyl ring is 67.22 (6)°. The non-coordinating pyrazolyl ring is twisted by 62.97 (7)° from the pyridyl ring. In the crystal, the complex cations are arranged in polymeric chains along the c-axis direction, with the nitrate counter-anions situated in between. Weak C—H⋯O hydrogen bonds link the ions into a three-dimensional network.

Keywords: crystal structure; silver(I) complex; one-dimensional coordination polymer; 2,6-bis[(1H-pyrazol-1-yl)methyl]pyridine.

CCDC reference: 1051419

1. Related literature

For related metal complexes, see: Reger et al. (2005 ); Sharma et al. (2011 ); Hurtado et al. (2011 ). For the synthesis of 2,6-bis[(1H-pyrazol-1-yl)methyl]pyridine, see: Singh et al. (2003 ); Son et al. (2014 ); Watson et al. (1987 ).

2. Experimental

2.1. Crystal data

[Ag(C₁₃H₁₃N₅)]NO₃
M_r = 409.16
Monoclinic, P 2₁ /c
a = 9.9604 (6) Å
b = 14.3192 (9) Å
c = 10.6878 (7) Å
β = 98.9100 (9)°
V = 1505.95 (16) Å³
Z = 4
Mo Kα radiation
μ = 1.36 mm⁻¹
T = 296 K
0.25 × 0.23 × 0.21 mm

2.2. Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.546, T_max = 0.726
12683 measured reflections
3618 independent reflections
3087 reflections with I > 2σ(I)
R_int = 0.017

2.3. Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.063
S = 1.04
3618 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1ⁱ	0.93	2.49	3.206 (3)	134
C4—H4A⋯O1ⁱ	0.97	2.48	3.347 (3)	149
C10—H10A⋯O3	0.97	2.38	3.277 (3)	154
C11—H11⋯O3ⁱⁱ	0.93	2.43	3.195 (3)	140
C13—H13⋯O1ⁱⁱⁱ	0.93	2.44	3.355 (3)	167
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y, -z+1; (iii) x, y, z+1.

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

CCDC reference: 1051419

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015004120/zq2231sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015004120/zq2231Isup2.hkl

checkCIF report

Structural commentary top

The metal complex with the tridentate ligand 2,6-bis((1H-pyrazol-1-yl)methyl)pyridine is reported as a catalyst of polyethylene polymerization (Hurtado et al., 2011; Watson et al., 1987). As a contribution to this field, we report herein the crystal structure of the title compound. In the cation part of the title compound, two ligands are linked by one silver atom. One pyrazolyl ring and the central pyridyl ring are coordinated to a second silver atom, as pictured in Fig 1. This bridging structure has shown that silver(I) complex can produce sophisticated coordination architectures and supramolecular arrays. The Ag—N distances are within the range of 2.165 (2) - 2.313 (2) Å with the silver atom in an almost trigonal planar arrangement and the sum of N—Ag—N angles being 359.5 ° with the range of 83.34 (6) - 139.15 (7) °. The crystal structure features π-π stacking interactions between pyridyl rings [centroid-centroid distance = 3.700 (3) Å] and geometric constraints imposed by coordination of the ligand to the silver atoms, as pictured in Fig 2.

Synthesis and crystallization top

To a stirred solution of Ag(NO₃) (0.051g, 0.3 mmol) in acetonitrile (5 ml) was added a solution of 2,6-bis((1H-pyrazol-1-yl)methyl)pyridine (0.072 g, 0.3 mmol) in acetonitrile (5 ml) at room temperature. After 24 h of stirring, a white powder was formed. The product was washed with diethyl ether. Single crystals of the title complex were obtained from its acetonitrile solution by slow evaporation of the solvent at room temperature within 2 weeks.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 - 0.98 Å, and with U_iso(H) = 1.2U_eq(C).

Related literature top

For related metal complexes, see: Reger et al. (2005); Sharma et al. (2011); Hurtado et al. (2011). For the synthesis of 2,6-bis[(1H-pyrazol-1-yl)methyl]pyridine, see: Singh et al. (2003); Son et al. (2014); Watson et al. (1987).

Structure description top

For related metal complexes, see: Reger et al. (2005); Sharma et al. (2011); Hurtado et al. (2011). For the synthesis of 2,6-bis[(1H-pyrazol-1-yl)methyl]pyridine, see: Singh et al. (2003); Son et al. (2014); Watson et al. (1987).

Synthesis and crystallization top

Refinement details top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 - 0.98 Å, and with U_iso(H) = 1.2U_eq(C).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. Structure of the title compound, showing the atom-numbering scheme and 30% probability ellipsoids [symmetry codes: (i) x, -y + 1/2, z + 1/2; (ii) x, -y + 1/2, z - 1/2].
	Fig. 2. Part of the crystal structure of the title complex, showing the 3-D network of molecules linked by weak C—H···O hydrogen bonds (dashed lines).

catena-Poly[[silver(I)-{µ-2,6-bis[(1H-pyrazol-1-yl)methyl]pyridine-κ³N¹,N²:N^2'}] nitrate] top

Crystal data top

[Ag(C₁₃H₁₃N₅)]NO₃	F(000) = 816
M_r = 409.16	D_x = 1.805 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6606 reflections
a = 9.9604 (6) Å	θ = 2.4–28.3°
b = 14.3192 (9) Å	µ = 1.36 mm⁻¹
c = 10.6878 (7) Å	T = 296 K
β = 98.9100 (9)°	Block, colourless
V = 1505.95 (16) Å³	0.25 × 0.23 × 0.21 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3087 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.017
φ and ω scans	θ_max = 28.3°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −13→13
T_min = 0.546, T_max = 0.726	k = −18→19
12683 measured reflections	l = −14→10
3618 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.027	H-atom parameters constrained
wR(F²) = 0.063	w = 1/[σ²(F_o²) + (0.0274P)² + 0.685P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
3618 reflections	Δρ_max = 0.43 e Å⁻³
208 parameters	Δρ_min = −0.39 e Å⁻³

Crystal data top

[Ag(C₁₃H₁₃N₅)]NO₃	V = 1505.95 (16) Å³
M_r = 409.16	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.9604 (6) Å	µ = 1.36 mm⁻¹
b = 14.3192 (9) Å	T = 296 K
c = 10.6878 (7) Å	0.25 × 0.23 × 0.21 mm
β = 98.9100 (9)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3618 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	3087 reflections with I > 2σ(I)
T_min = 0.546, T_max = 0.726	R_int = 0.017
12683 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.063	H-atom parameters constrained
S = 1.04	Δρ_max = 0.43 e Å⁻³
3618 reflections	Δρ_min = −0.39 e Å⁻³
208 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
Ag1	0.11928 (2)	0.23756 (2)	0.31490 (2)	0.04028 (7)
N1	−0.04629 (18)	0.16608 (14)	0.17705 (18)	0.0399 (4)
N2	−0.17162 (18)	0.15774 (13)	0.20861 (17)	0.0370 (4)
N3	0.00565 (16)	0.17147 (12)	0.46594 (15)	0.0297 (4)
N4	0.30868 (17)	0.12786 (13)	0.70046 (17)	0.0341 (4)
N5	0.28527 (18)	0.16529 (13)	0.81157 (16)	0.0358 (4)
C1	−0.0480 (2)	0.11349 (17)	0.0749 (2)	0.0433 (5)
H1	0.0253	0.106	0.0314	0.052*
C2	−0.1733 (3)	0.07115 (19)	0.0413 (3)	0.0516 (6)
H2	−0.1996	0.0308	−0.0263	0.062*
C3	−0.2497 (2)	0.10127 (19)	0.1282 (2)	0.0494 (6)
H3	−0.3397	0.0855	0.1313	0.059*
C4	−0.2034 (2)	0.20274 (17)	0.3231 (2)	0.0397 (5)
H4A	−0.3006	0.1994	0.3237	0.048*
H4B	−0.1782	0.2681	0.3225	0.048*
C5	−0.1295 (2)	0.15704 (15)	0.4414 (2)	0.0330 (5)
C6	−0.1955 (2)	0.10294 (17)	0.5200 (2)	0.0434 (6)
H6	−0.2892	0.0949	0.503	0.052*
C7	−0.1202 (2)	0.06098 (17)	0.6244 (2)	0.0446 (6)
H7	−0.1625	0.0235	0.6777	0.053*
C8	0.0186 (2)	0.07517 (15)	0.6487 (2)	0.0371 (5)
H8	0.071	0.0472	0.7183	0.044*
C9	0.0783 (2)	0.13177 (14)	0.56789 (19)	0.0302 (4)
C10	0.2274 (2)	0.15549 (16)	0.58221 (19)	0.0349 (5)
H10A	0.2649	0.1262	0.5135	0.042*
H10B	0.236	0.2225	0.5728	0.042*
C11	0.4251 (2)	0.07940 (18)	0.7160 (3)	0.0478 (6)
H11	0.4625	0.0485	0.653	0.057*
C12	0.4785 (3)	0.08368 (19)	0.8407 (3)	0.0569 (7)
H12	0.5584	0.056	0.8802	0.068*
C13	0.3895 (2)	0.13761 (18)	0.8967 (2)	0.0472 (6)
H13	0.4008	0.1526	0.9824	0.057*
N6	0.3934 (2)	0.12375 (14)	0.2741 (2)	0.0463 (5)
O1	0.46828 (19)	0.16474 (15)	0.21131 (19)	0.0656 (5)
O2	0.2747 (2)	0.10663 (15)	0.2250 (3)	0.0822 (7)
O3	0.4345 (3)	0.10089 (19)	0.3834 (2)	0.1001 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.03190 (10)	0.04830 (12)	0.04040 (12)	−0.00783 (7)	0.00483 (8)	0.00771 (8)
N1	0.0312 (10)	0.0513 (11)	0.0371 (11)	−0.0051 (8)	0.0042 (8)	−0.0017 (9)
N2	0.0272 (9)	0.0495 (11)	0.0323 (10)	0.0015 (8)	−0.0017 (8)	−0.0004 (8)
N3	0.0264 (9)	0.0379 (9)	0.0242 (9)	−0.0010 (7)	0.0022 (7)	−0.0021 (7)
N4	0.0288 (9)	0.0437 (10)	0.0286 (9)	0.0067 (7)	0.0004 (7)	−0.0031 (8)
N5	0.0343 (10)	0.0439 (10)	0.0273 (10)	0.0078 (8)	−0.0011 (8)	−0.0022 (8)
C1	0.0387 (13)	0.0558 (14)	0.0350 (13)	0.0032 (11)	0.0039 (10)	−0.0005 (11)
C2	0.0455 (15)	0.0637 (16)	0.0419 (15)	0.0022 (12)	−0.0052 (12)	−0.0141 (12)
C3	0.0292 (12)	0.0692 (17)	0.0460 (15)	−0.0055 (11)	−0.0058 (11)	−0.0096 (12)
C4	0.0275 (11)	0.0533 (13)	0.0368 (13)	0.0064 (9)	0.0005 (9)	−0.0047 (10)
C5	0.0266 (11)	0.0411 (12)	0.0309 (12)	−0.0005 (8)	0.0031 (9)	−0.0066 (9)
C6	0.0282 (11)	0.0580 (15)	0.0448 (14)	−0.0100 (10)	0.0077 (10)	−0.0079 (11)
C7	0.0483 (15)	0.0517 (14)	0.0354 (13)	−0.0156 (11)	0.0121 (11)	0.0005 (11)
C8	0.0428 (13)	0.0395 (12)	0.0284 (11)	−0.0035 (9)	0.0039 (10)	0.0006 (9)
C9	0.0308 (11)	0.0341 (10)	0.0254 (10)	0.0001 (8)	0.0032 (8)	−0.0048 (8)
C10	0.0291 (11)	0.0501 (13)	0.0246 (11)	0.0002 (9)	0.0011 (9)	−0.0001 (9)
C11	0.0329 (12)	0.0548 (15)	0.0540 (16)	0.0134 (11)	0.0018 (11)	−0.0095 (12)
C12	0.0395 (14)	0.0646 (17)	0.0591 (18)	0.0201 (12)	−0.0158 (13)	−0.0025 (13)
C13	0.0441 (14)	0.0576 (15)	0.0340 (13)	0.0079 (11)	−0.0125 (10)	−0.0022 (11)
N6	0.0419 (12)	0.0504 (12)	0.0502 (13)	0.0160 (9)	0.0181 (11)	0.0031 (10)
O1	0.0448 (11)	0.0948 (15)	0.0613 (13)	−0.0115 (10)	0.0212 (10)	0.0002 (11)
O2	0.0391 (11)	0.0674 (14)	0.141 (2)	−0.0078 (10)	0.0174 (13)	−0.0111 (13)
O3	0.138 (2)	0.119 (2)	0.0488 (13)	0.0729 (18)	0.0331 (14)	0.0239 (13)

Geometric parameters (Å, º) top

Ag1—N5ⁱ	2.1652 (17)	C4—H4A	0.97
Ag1—N1	2.2772 (19)	C4—H4B	0.97
Ag1—N3	2.3126 (16)	C5—C6	1.382 (3)
N1—C1	1.325 (3)	C6—C7	1.381 (3)
N1—N2	1.348 (3)	C6—H6	0.93
N2—C3	1.338 (3)	C7—C8	1.382 (3)
N2—C4	1.461 (3)	C7—H7	0.93
N3—C9	1.338 (3)	C8—C9	1.384 (3)
N3—C5	1.347 (2)	C8—H8	0.93
N4—C11	1.340 (3)	C9—C10	1.508 (3)
N4—N5	1.356 (2)	C10—H10A	0.97
N4—C10	1.446 (3)	C10—H10B	0.97
N5—C13	1.331 (3)	C11—C12	1.358 (4)
N5—Ag1ⁱⁱ	2.1652 (17)	C11—H11	0.93
C1—C2	1.384 (3)	C12—C13	1.380 (4)
C1—H1	0.93	C12—H12	0.93
C2—C3	1.359 (4)	C13—H13	0.93
C2—H2	0.93	N6—O3	1.222 (3)
C3—H3	0.93	N6—O1	1.227 (3)
C4—C5	1.510 (3)	N6—O2	1.241 (3)

N5ⁱ—Ag1—N1	139.15 (7)	N3—C5—C6	121.5 (2)
N5ⁱ—Ag1—N3	137.05 (6)	N3—C5—C4	116.07 (18)
N1—Ag1—N3	83.34 (6)	C6—C5—C4	122.41 (19)
C1—N1—N2	105.18 (18)	C7—C6—C5	119.0 (2)
C1—N1—Ag1	134.79 (16)	C7—C6—H6	120.5
N2—N1—Ag1	118.94 (14)	C5—C6—H6	120.5
C3—N2—N1	111.20 (19)	C6—C7—C8	119.4 (2)
C3—N2—C4	128.7 (2)	C6—C7—H7	120.3
N1—N2—C4	120.01 (18)	C8—C7—H7	120.3
C9—N3—C5	119.42 (17)	C7—C8—C9	118.8 (2)
C9—N3—Ag1	118.76 (13)	C7—C8—H8	120.6
C5—N3—Ag1	120.62 (13)	C9—C8—H8	120.6
C11—N4—N5	111.05 (18)	N3—C9—C8	121.82 (19)
C11—N4—C10	127.36 (19)	N3—C9—C10	112.75 (18)
N5—N4—C10	120.55 (17)	C8—C9—C10	125.43 (19)
C13—N5—N4	105.05 (18)	N4—C10—C9	115.87 (18)
C13—N5—Ag1ⁱⁱ	134.18 (16)	N4—C10—H10A	108.3
N4—N5—Ag1ⁱⁱ	120.26 (13)	C9—C10—H10A	108.3
N1—C1—C2	111.0 (2)	N4—C10—H10B	108.3
N1—C1—H1	124.5	C9—C10—H10B	108.3
C2—C1—H1	124.5	H10A—C10—H10B	107.4
C3—C2—C1	105.2 (2)	N4—C11—C12	107.3 (2)
C3—C2—H2	127.4	N4—C11—H11	126.3
C1—C2—H2	127.4	C12—C11—H11	126.3
N2—C3—C2	107.4 (2)	C11—C12—C13	105.7 (2)
N2—C3—H3	126.3	C11—C12—H12	127.1
C2—C3—H3	126.3	C13—C12—H12	127.1
N2—C4—C5	111.67 (18)	N5—C13—C12	110.8 (2)
N2—C4—H4A	109.3	N5—C13—H13	124.6
C5—C4—H4A	109.3	C12—C13—H13	124.6
N2—C4—H4B	109.3	O3—N6—O1	120.6 (3)
C5—C4—H4B	109.3	O3—N6—O2	120.5 (3)
H4A—C4—H4B	107.9	O1—N6—O2	118.9 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱⁱⁱ	0.93	2.49	3.206 (3)	134
C4—H4A···O1ⁱⁱⁱ	0.97	2.48	3.347 (3)	149
C10—H10A···O3	0.97	2.38	3.277 (3)	154
C11—H11···O3^iv	0.93	2.43	3.195 (3)	140
C13—H13···O1^v	0.93	2.44	3.355 (3)	167

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.93	2.49	3.206 (3)	134
C4—H4A···O1ⁱ	0.97	2.48	3.347 (3)	149
C10—H10A···O3	0.97	2.38	3.277 (3)	154
C11—H11···O3ⁱⁱ	0.93	2.43	3.195 (3)	140
C13—H13···O1ⁱⁱⁱ	0.93	2.44	3.355 (3)	167

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

Acknowledgements

This work was supported by the research fund of Chungnam National University.

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ISSN: 2056-9890

Volume 71| Part 4| April 2015| Pages m79-m80

doi:10.1107/S2056989015004120

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