catena-Poly[[silver(I)-μ-2-[(pyrazin-2-yl-κ2N1:N4)amino­meth­yl]phenol] nitrate]

Deng, Z.-P.; Gao, S.; Ng, S.W.

doi:10.1107/S1600536812034769

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page m1171

doi:10.1107/S1600536812034769

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catena-Poly[[silver(I)-μ-2-[(pyrazin-2-yl-κ²N¹:N⁴)aminomethyl]phenol] nitrate]

Zhao-Peng Deng,^a Shan Gao ^a and Seik Weng Ng ^b,^c ^*

^aKey Laboratory of Functional Inorganic Material Chemistry, Ministry of Education, Heilongjiang University, Harbin 150080, People's Republic of China, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 31 July 2012; accepted 6 August 2012; online 11 August 2012)

The Ag^I atom in the polycationic salt, {[Ag(C₁₁H₁₁N₃O)]NO₃}_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 NO₃⁻ counter-ions surround the polymeric chain and interact 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_r = 371.11
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.043
wR(F²) = 0.125
S = 1.02
2864 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.77 e Å⁻³

Table 1
Selected bond lengths (Å)

Ag1—N1	2.172 (4)
Ag1—N2ⁱ	2.195 (4)
Symmetry code: (i) x-1, y, z.

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) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x, -y+1, -z+1.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812034769/xu5602sup1.cif

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

checkCIF report

Comment top

A recent study reports 2-[(pyrazin-2-ylamino)methyl]phenol, a reduced Schiff-base that possesses an acidic phenolic group (Gao & Ng, 2012). The reaction with silver nitrate yields polycationic [Ag(C₁₁H₁₁N₃O)]_n nNO₃ (Scheme I). The polymeric nature arises from bridging by the pyrazine portion of the ligand. The counterions surround the chain and interact only weakly with it [Ag···O 2.701 (4), 2.810 (5) Å] (Fig. 1). Adjacent chains are linked into a three-dimensional network by O–H···O and N–H···O hydrogen bonds (Table 1).

Related literature top

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

Experimental top

An acetonitrile solution (10 ml) of silver nitrate (1 mmol) was added to a methanol solution (5 ml) of 2-[(pyrazin-2-ylamino)methyl]phenol (1 mmol). The solution was filtered and then side aside, away from light, for the growth of crystals. Colorless crystals were obtained after several days.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); 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).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the polymeric chain structure of [Ag(C₁₁H₁₁N₃O)]_nNO₃ at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

catena-Poly[[silver(I)-µ-2-[(pyrazin-2-yl- κ²N¹:N⁴)aminomethyl]phenol] nitrate] top

Crystal data top

[Ag(C₁₁H₁₁N₃O)]NO₃	F(000) = 736
M_r = 371.11	D_x = 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

Data collection top

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

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0508P)² + 4.1394P] where P = (F_o² + 2F_c²)/3
2864 reflections	(Δ/σ)_max = 0.001
182 parameters	Δρ_max = 0.64 e Å⁻³
0 restraints	Δρ_min = −0.77 e Å⁻³

Crystal data top

[Ag(C₁₁H₁₁N₃O)]NO₃	V = 1256.1 (3) Å³
M_r = 371.11	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.1265 (9) Å	µ = 1.63 mm⁻¹
b = 9.5249 (14) Å	T = 293 K
c = 18.654 (2) Å	0.27 × 0.18 × 0.13 mm
β = 97.240 (4)°

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	2864 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2038 reflections with I > 2σ(I)
T_min = 0.668, T_max = 0.817	R_int = 0.042
11969 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.02	Δρ_max = 0.64 e Å⁻³
2864 reflections	Δρ_min = −0.77 e Å⁻³
182 parameters

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3^iv	0.84	1.96	2.795 (6)	171
N3—H3···O4ⁱⁱ	0.88	2.22	2.982 (6)	145

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

Experimental details

Crystal data
Chemical formula	[Ag(C₁₁H₁₁N₃O)]NO₃
M_r	371.11
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.1265 (9), 9.5249 (14), 18.654 (2)
β (°)	97.240 (4)
V (Å³)	1256.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.63
Crystal size (mm)	0.27 × 0.18 × 0.13

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.668, 0.817
No. of measured, independent and observed [I > 2σ(I)] reflections	11969, 2864, 2038
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.125, 1.02
No. of reflections	2864
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.77

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Ag1—N1

2.172 (4)

Ag1—N2ⁱ

2.195 (4)

Symmetry code: (i) x−1, y, z.

Hydrogen-bond geometry (Å, º) top

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) x, −y+3/2, z+1/2; (iii) −x, −y+1, −z+1.

Acknowledgements

We thank the Key Project of the Natural Science Foundation of Heilongjiang Province (No. ZD200903), the Key Project of the Education Bureau of Heilongjiang Province (No. 12511z023, No. 2011CJHB006), the Innovation Team of the Education Bureau of Heilongjiang Province (No. 2010 t d03), Heilongjiang University (Hdtd2010–04) and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.

References

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