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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536812034769/xu5602sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536812034769/xu5602Isup2.hkl
Contains datablock I

CCDC reference: 899579

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.043
  • wR factor = 0.125
  • Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors of N4 PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 6.690 PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 3 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 2
Alert level G PLAT004_ALERT_5_G Info: Polymeric Structure Found with Dimension . 1 PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF .... ? PLAT007_ALERT_5_G Note: Number of Unrefined D-H Atoms ............ 2 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature 293 K PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) . 1.14 Ratio PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 18
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 4 ALERT level C = Check. Ensure it is not caused by an omission or oversight 7 ALERT level G = General information/check it is not something unexpected 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 3 ALERT type 5 Informative message, check

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.

Refinement top

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 refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C,N,O).

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
[Figure 1] 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)]NO3F(000) = 736
Mr = 371.11Dx = 1.962 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5867 reflections
a = 7.1265 (9) Åθ = 3.1–27.5°
b = 9.5249 (14) ŵ = 1.63 mm1
c = 18.654 (2) ÅT = 293 K
β = 97.240 (4)°Prism, colorless
V = 1256.1 (3) Å30.27 × 0.18 × 0.13 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer
2864 independent reflections
Radiation source: fine-focus sealed tube2038 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
ω scanθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 98
Tmin = 0.668, Tmax = 0.817k = 1212
11969 measured reflectionsl = 2424
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H-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 parametersΔρmax = 0.64 e Å3
0 restraintsΔρmin = 0.77 e Å3
Crystal data top
[Ag(C11H11N3O)]NO3V = 1256.1 (3) Å3
Mr = 371.11Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.1265 (9) ŵ = 1.63 mm1
b = 9.5249 (14) ÅT = 293 K
c = 18.654 (2) Å0.27 × 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)
Tmin = 0.668, Tmax = 0.817Rint = 0.042
11969 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.125H-atom parameters constrained
S = 1.02Δρmax = 0.64 e Å3
2864 reflectionsΔρmin = 0.77 e Å3
182 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ag10.06666 (5)0.59659 (5)0.58246 (2)0.05110 (18)
O10.3023 (5)0.4649 (5)0.8136 (2)0.0571 (10)
H10.25820.52910.83750.086*
O20.0170 (6)0.6917 (5)0.4458 (2)0.0575 (11)
O30.1837 (5)0.8322 (5)0.4064 (2)0.0574 (11)
O40.0257 (6)0.7272 (6)0.3321 (2)0.0658 (12)
N10.3716 (5)0.5848 (4)0.5842 (2)0.0316 (8)
N20.7616 (5)0.5983 (4)0.5896 (2)0.0361 (9)
N30.4029 (6)0.4097 (5)0.6707 (2)0.0434 (10)
H30.27850.40810.66610.052*
N40.0450 (6)0.7509 (5)0.3943 (2)0.0414 (10)
C10.4556 (6)0.6685 (5)0.5406 (3)0.0352 (10)
H1A0.38040.72450.50780.042*
C20.6473 (7)0.6755 (5)0.5421 (3)0.0397 (11)
H20.69930.73410.51000.048*
C30.6828 (6)0.5159 (6)0.6338 (3)0.0368 (11)
H3A0.75990.46480.66830.044*
C40.4845 (6)0.5027 (5)0.6304 (2)0.0328 (10)
C50.5036 (8)0.3108 (6)0.7217 (3)0.0442 (12)
H5A0.60010.26420.69800.053*
H5B0.41510.23950.73330.053*
C60.5967 (7)0.3745 (5)0.7914 (3)0.0371 (11)
C70.7896 (7)0.3554 (6)0.8134 (3)0.0451 (12)
H70.86250.30620.78390.054*
C80.8733 (8)0.4086 (6)0.8783 (3)0.0510 (14)
H81.00160.39410.89260.061*
C90.7677 (8)0.4832 (7)0.9221 (3)0.0529 (14)
H90.82470.51920.96580.063*
C100.5791 (8)0.5042 (6)0.9013 (3)0.0472 (13)
H100.50820.55520.93080.057*
C110.4926 (7)0.4498 (6)0.8363 (3)0.0404 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.0201 (2)0.0684 (3)0.0657 (3)0.00250 (18)0.00874 (18)0.0059 (2)
O10.039 (2)0.071 (3)0.062 (3)0.008 (2)0.0080 (19)0.008 (2)
O20.050 (2)0.066 (3)0.059 (2)0.000 (2)0.018 (2)0.015 (2)
O30.039 (2)0.064 (3)0.067 (3)0.0142 (19)0.0030 (19)0.011 (2)
O40.048 (2)0.102 (4)0.047 (2)0.010 (2)0.0027 (19)0.012 (2)
N10.0186 (16)0.038 (2)0.038 (2)0.0005 (15)0.0023 (15)0.0005 (17)
N20.0183 (16)0.044 (2)0.046 (2)0.0003 (16)0.0028 (16)0.0007 (19)
N30.028 (2)0.059 (3)0.043 (2)0.006 (2)0.0052 (18)0.010 (2)
N40.028 (2)0.046 (3)0.050 (3)0.0013 (18)0.0086 (19)0.002 (2)
C10.024 (2)0.035 (3)0.047 (3)0.0019 (19)0.005 (2)0.004 (2)
C20.029 (2)0.041 (3)0.050 (3)0.002 (2)0.012 (2)0.008 (2)
C30.022 (2)0.048 (3)0.041 (3)0.005 (2)0.0058 (19)0.002 (2)
C40.025 (2)0.041 (3)0.034 (2)0.0041 (19)0.0101 (18)0.007 (2)
C50.042 (3)0.046 (3)0.045 (3)0.002 (2)0.010 (2)0.003 (2)
C60.038 (2)0.036 (3)0.039 (3)0.001 (2)0.009 (2)0.007 (2)
C70.038 (3)0.047 (3)0.051 (3)0.005 (2)0.013 (2)0.014 (3)
C80.035 (3)0.049 (3)0.067 (4)0.002 (2)0.002 (3)0.014 (3)
C90.052 (3)0.053 (4)0.051 (3)0.008 (3)0.005 (3)0.003 (3)
C100.052 (3)0.046 (3)0.044 (3)0.002 (3)0.010 (3)0.006 (2)
C110.035 (2)0.040 (3)0.047 (3)0.001 (2)0.007 (2)0.005 (2)
Geometric parameters (Å, º) top
Ag1—N12.172 (4)C1—H1A0.9300
Ag1—N2i2.195 (4)C2—H20.9300
Ag1—O22.701 (4)C3—C41.412 (6)
Ag1—O2ii2.810 (5)C3—H3A0.9300
O1—C111.376 (6)C5—C61.511 (7)
O1—H10.8400C5—H5A0.9700
O2—N41.242 (6)C5—H5B0.9700
O3—N41.254 (6)C6—C71.396 (7)
O4—N41.225 (6)C6—C111.386 (7)
N1—C11.333 (6)C7—C81.377 (8)
N1—C41.352 (6)C7—H70.9300
N2—C31.314 (6)C8—C91.376 (9)
N2—C21.344 (6)C8—H80.9300
N2—Ag1iii2.195 (4)C9—C101.366 (8)
N3—C41.342 (6)C9—H90.9300
N3—C51.461 (7)C10—C111.390 (8)
N3—H30.8800C10—H100.9300
C1—C21.364 (6)
N1—Ag1—N2i175.01 (15)C4—C3—H3A119.0
N1—Ag1—O297.63 (13)N1—C4—N3118.3 (4)
N2i—Ag1—O287.27 (14)N1—C4—C3119.3 (4)
N1—Ag1—O2ii93.12 (13)N3—C4—C3122.4 (5)
N2i—Ag1—O2ii85.21 (14)N3—C5—C6115.3 (4)
O2—Ag1—O2ii98.24 (12)N3—C5—H5A108.5
C11—O1—H1109.5C6—C5—H5A108.5
N4—O2—Ag1145.6 (3)N3—C5—H5B108.5
C1—N1—C4117.2 (4)C6—C5—H5B108.5
C1—N1—Ag1119.1 (3)H5A—C5—H5B107.5
C4—N1—Ag1123.6 (3)C7—C6—C11118.1 (5)
C3—N2—C2117.9 (4)C7—C6—C5120.7 (5)
C3—N2—Ag1iii122.6 (3)C11—C6—C5121.2 (5)
C2—N2—Ag1iii119.1 (3)C6—C7—C8120.8 (5)
C4—N3—C5125.3 (4)C6—C7—H7119.6
C4—N3—H3117.3C8—C7—H7119.6
C5—N3—H3117.3C9—C8—C7120.2 (5)
O4—N4—O2120.3 (5)C9—C8—H8119.9
O4—N4—O3120.3 (5)C7—C8—H8119.9
O2—N4—O3119.4 (5)C8—C9—C10120.0 (5)
N1—C1—C2122.9 (5)C8—C9—H9120.0
N1—C1—H1A118.6C10—C9—H9120.0
C2—C1—H1A118.6C9—C10—C11120.3 (5)
C1—C2—N2120.6 (4)C9—C10—H10119.8
C1—C2—H2119.7C11—C10—H10119.8
N2—C2—H2119.7C6—C11—C10120.5 (5)
N2—C3—C4121.9 (4)C6—C11—O1116.7 (5)
N2—C3—H3A119.0C10—C11—O1122.7 (5)
N1—Ag1—O2—N419.9 (6)C5—N3—C4—N1178.2 (5)
N2i—Ag1—O2—N4161.0 (6)C5—N3—C4—C30.7 (8)
O2ii—Ag1—O2—N4114.2 (6)N2—C3—C4—N15.1 (7)
O2—Ag1—N1—C126.1 (4)N2—C3—C4—N3173.8 (5)
O2ii—Ag1—N1—C1124.9 (4)C4—N3—C5—C673.9 (6)
O2ii—Ag1—N1—C459.3 (4)N3—C5—C6—C7124.6 (5)
Ag1—O2—N4—O4152.0 (5)N3—C5—C6—C1157.3 (6)
Ag1—O2—N4—O326.1 (9)C11—C6—C7—C80.7 (8)
C4—N1—C1—C21.2 (7)C5—C6—C7—C8177.4 (5)
Ag1—N1—C1—C2174.9 (4)C6—C7—C8—C90.8 (8)
N1—C1—C2—N21.3 (8)C7—C8—C9—C100.2 (9)
C3—N2—C2—C10.5 (7)C8—C9—C10—C110.5 (9)
Ag1iii—N2—C2—C1173.7 (4)C7—C6—C11—C100.1 (8)
C2—N2—C3—C42.6 (7)C5—C6—C11—C10178.1 (5)
Ag1iii—N2—C3—C4170.3 (4)C7—C6—C11—O1179.0 (5)
C1—N1—C4—N3174.8 (4)C5—C6—C11—O10.9 (7)
Ag1—N1—C4—N39.2 (6)C9—C10—C11—C60.6 (8)
C1—N1—C4—C34.2 (7)C9—C10—C11—O1178.4 (5)
Ag1—N1—C4—C3171.8 (3)
Symmetry codes: (i) x1, y, z; (ii) x, y+1, z+1; (iii) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O3iv0.841.962.795 (6)171
N3—H3···O4ii0.882.222.982 (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
Mr371.11
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)7.1265 (9), 9.5249 (14), 18.654 (2)
β (°) 97.240 (4)
V3)1256.1 (3)
Z4
Radiation typeMo Kα
µ (mm1)1.63
Crystal size (mm)0.27 × 0.18 × 0.13
Data collection
DiffractometerRigaku R-AXIS RAPID IP
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.668, 0.817
No. of measured, independent and
observed [I > 2σ(I)] reflections
11969, 2864, 2038
Rint0.042
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.125, 1.02
No. of reflections2864
No. of parameters182
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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—N12.172 (4)Ag1—N2i2.195 (4)
Symmetry code: (i) x1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O3ii0.841.962.795 (6)171
N3—H3···O4iii0.882.222.982 (6)145
Symmetry codes: (ii) x, y+3/2, z+1/2; (iii) x, y+1, z+1.
 

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