metal-organic compounds
catena-Poly[[silver(I)-μ-2-[(pyrazin-2-yl-κ2N1:N4)aminomethyl]phenol] nitrate]
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
The AgI 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
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Refinement
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Data collection: RAPID-AUTO (Rigaku, 1998); cell 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
10.1107/S1600536812034769/xu5602sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812034769/xu5602Isup2.hkl
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.
Hydrogen atoms were placed in calculated positions (C–H 0.93–0.97, N–H 0.88, O–H 0.84 Å) and were included in the
in the riding model approximation, with U(H) set to 1.2–1.5U(C,N,O).Data collection: RAPID-AUTO (Rigaku, 1998); cell
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).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. |
[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 |
[Ag(C11H11N3O)]NO3 | V = 1256.1 (3) Å3 |
Mr = 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)° |
Rigaku R-AXIS RAPID IP diffractometer | 2864 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 2038 reflections with I > 2σ(I) |
Tmin = 0.668, Tmax = 0.817 | Rint = 0.042 |
11969 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.125 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.64 e Å−3 |
2864 reflections | Δρmin = −0.77 e Å−3 |
182 parameters |
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) |
Symmetry codes: (i) x−1, y, z; (ii) −x, −y+1, −z+1; (iii) x+1, y, z. |
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 |
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 |
Mr | 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) |
Tmin, Tmax | 0.668, 0.817 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11969, 2864, 2038 |
Rint | 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 |
Δρmax, Δρmin (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).
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
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Gao, S. & Ng, S. W. (2012). Acta Cryst. E68, o2472. CSD CrossRef IUCr Journals Google Scholar
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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).