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In the title compound, [Ag(C2H4N4)2](NO3)·C2H4N4, the Ag atom is surrounded by three cyano­guanidine (cnge) mol­ecules. Two monodentate cnge mol­ecules form strong covalent Ag-N bonds of 2.210 (7) and 2.266 (6) Å through their nitrile N atoms. The third cnge mol­ecule is located in a vacant crystal site and is only weakly coordinated to the Ag atom as a solvate molecule. Inter- and intramolecular hydrogen bonds play an important role in the crystal packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103008357/jz1551sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103008357/jz1551Isup2.hkl
Contains datablock I

CCDC reference: 214381

Comment top

Cyanoguanidine (cnge; Scheme 1), which is the dimeric form of cyanamide (H2NCN) and a commercially important compound, is a versatile precursor for the syntheses of organonitrogen compounds; its coordination chemistry has been intensively studied because of its differing functional groups. Cnge readily coordinates to the later transition metals, and the coordination typically occurs through the nitrile N atom. Complexes with copper(II) (Chiesi et al., 1971; Hubberstey et al., 1997, 1993), copper(I) (Hubberstey et al., 1996), zinc(II) (Pickardt & Kühn, 1996; Harrison et al., 2001), cadmium(II) and mercury (II) (Pickardt & Kühn, 1996), and nickel(II) (Meyer et al., 2000) have been reported, but no crystal structure of a silver–cnge complex has been known up to now.

A labelled displacement ellipsoid plot of the coordination motifs of [Ag(C2H4N4)3]NO3 is shown in Fig. 1, and bond distances and angles are given in Table 1. The Ag atom is surrounded by three cnge molecules, two of which behave as monodentate ligands through nitrile N atoms. The Ag—N(21) and Ag—N(11) distances are 2.210 (7) and 2.266 (6) Å, respectively, and the N(11)—Ag(1)—N(12) angle is 175.5 (2)°, almost linear, a common geometry in 2-coordinate AgI complexes. The interactions of the Ag atom with two N31 atoms, viz. one at 2.596 (7) Å within the asymmetric unit and the other at 2.681 (7) Å (symmetry operator: x, -1 + y, z), are longer than the sum of the covalent distances and much weaker. Thus, the third cnge molecule is almost uncoordinated and essentially located in a vacant crystal site. Typical Ag—N distances are 2.11–2.16 Å for 2-coordinate silver in AgN(CN)2 (Britton, 1990) and silver-pyzazolate complexes (Mohamed & Fakler Jr., 2002), 2.22 Å for 3-coordinate silver in AgC(CN)3 (Konnert & Britton, 1966), and 2.23 Å for 4-coordinate silver in AgC(CN)2NO (Chow & Britton, 1974) and silver 1,10-decanedinitrile complexes (Carlucci et al., 1999). The elongated 2-coordinate Ag—N distances are probably caused by the effects of four further Ag···N interactions [two with N31, as mentioned above, and two with N11, viz. 2.795 (7) and 2.860 (7) Å: symmetry operators 1/2 - x, -1/2 + y, 1/2 - z and 1/2 - x, 1/2 + y, 1/2 - z respectively). The Ag atom is coplanar with the three surrounding N atoms but not with the three cnge molecules. The angles Ag—N11—C12 [140.2 (5)°] and Ag—N21—C22 [167.6 (6)°] are smaller than those expected for a transition metal–nitrile interaction (180°) because of the hydrogen bonding (N16—H···N31 and N35—H···N21; Fig. 2 and Table 2). Such a distortion of the coordination geometry has also been observed in [Cu(OAc)2(cnge)2]2 (Begley et al., 1993).

The hydrogen bonds are listed in Table 2. cnge is a hydrogen-bonding ligand that may act both as a donor (amino, NH2) and as an acceptor (cyanimino, N—CN). The N—H donor systems from both amino groups have close contacts to the nitrate anion [Fig. 2; hydrogen bond type (i)], and there is also hydrogen bonding between imino and amino N atoms of neighboring molecules [Fig. 2; hydrogen bond type (ii)]. In addition, there is intramolecular hydrogen bonding between amino and nitrile N atoms [Fig. 2; hydrogen bond type (iii)]. The above- mentioned three hydrogen-bonding modes have been reviewed for cnge coordination compounds by Hubberstey et al. (1997). The overall hydrogen bonding promotes the two-dimensional sheet structure and stabilizes the crystal architecture.

All three cnge molecules are planar within crystallographic resolution, and the maximum distances from the least-squares plane are 0.025 (N11—N16 ligand), 0.008 (N21—N26 ligand) and 0.013 (N31—N36 ligand) Å. The individual coordination does not severely affect the structural parameters of cnge (Fernanda et al., 1993). The shortest Ag—Ag distance along b is 3.648 (1) Å, parallel to the 21 axis. The structure as a whole consists of layers stacked along the b direction, which is also the direction of fast crystal growth.

Experimental top

[Ag(C2H4N4)3]NO3 was prepared by mixing AgNO3 (34.0 mg, 0.2 mmol) and H2NCN (cyanamide; Aldrich; 50.4 mg, 1.2 mmol) in diethylether (10 ml), yielding a colorless solution. Slow addition of hexane caused the complex to crystallize as long colorless needles (Scheme 2). These were separated by filtration, washed with diethyl ether and hexane, and dried in a desiccator over P2O5. An IR spectrum indicated a nitrile unit (major absorption at 2150 cm-1) and a series of N—H groups in the range 3200–3450 cm-1; the elemental analysis agrees with the title composition.

Refinement top

All H atoms were found from ΔF maps and were refined freely, with all N—H bond distances restrained to be equal within an effective standard deviation of 0.02 Å (SADI instruction in SHELXL97). H atoms were assigned a common isotropic displacement parameter.

Structure description top

Cyanoguanidine (cnge; Scheme 1), which is the dimeric form of cyanamide (H2NCN) and a commercially important compound, is a versatile precursor for the syntheses of organonitrogen compounds; its coordination chemistry has been intensively studied because of its differing functional groups. Cnge readily coordinates to the later transition metals, and the coordination typically occurs through the nitrile N atom. Complexes with copper(II) (Chiesi et al., 1971; Hubberstey et al., 1997, 1993), copper(I) (Hubberstey et al., 1996), zinc(II) (Pickardt & Kühn, 1996; Harrison et al., 2001), cadmium(II) and mercury (II) (Pickardt & Kühn, 1996), and nickel(II) (Meyer et al., 2000) have been reported, but no crystal structure of a silver–cnge complex has been known up to now.

A labelled displacement ellipsoid plot of the coordination motifs of [Ag(C2H4N4)3]NO3 is shown in Fig. 1, and bond distances and angles are given in Table 1. The Ag atom is surrounded by three cnge molecules, two of which behave as monodentate ligands through nitrile N atoms. The Ag—N(21) and Ag—N(11) distances are 2.210 (7) and 2.266 (6) Å, respectively, and the N(11)—Ag(1)—N(12) angle is 175.5 (2)°, almost linear, a common geometry in 2-coordinate AgI complexes. The interactions of the Ag atom with two N31 atoms, viz. one at 2.596 (7) Å within the asymmetric unit and the other at 2.681 (7) Å (symmetry operator: x, -1 + y, z), are longer than the sum of the covalent distances and much weaker. Thus, the third cnge molecule is almost uncoordinated and essentially located in a vacant crystal site. Typical Ag—N distances are 2.11–2.16 Å for 2-coordinate silver in AgN(CN)2 (Britton, 1990) and silver-pyzazolate complexes (Mohamed & Fakler Jr., 2002), 2.22 Å for 3-coordinate silver in AgC(CN)3 (Konnert & Britton, 1966), and 2.23 Å for 4-coordinate silver in AgC(CN)2NO (Chow & Britton, 1974) and silver 1,10-decanedinitrile complexes (Carlucci et al., 1999). The elongated 2-coordinate Ag—N distances are probably caused by the effects of four further Ag···N interactions [two with N31, as mentioned above, and two with N11, viz. 2.795 (7) and 2.860 (7) Å: symmetry operators 1/2 - x, -1/2 + y, 1/2 - z and 1/2 - x, 1/2 + y, 1/2 - z respectively). The Ag atom is coplanar with the three surrounding N atoms but not with the three cnge molecules. The angles Ag—N11—C12 [140.2 (5)°] and Ag—N21—C22 [167.6 (6)°] are smaller than those expected for a transition metal–nitrile interaction (180°) because of the hydrogen bonding (N16—H···N31 and N35—H···N21; Fig. 2 and Table 2). Such a distortion of the coordination geometry has also been observed in [Cu(OAc)2(cnge)2]2 (Begley et al., 1993).

The hydrogen bonds are listed in Table 2. cnge is a hydrogen-bonding ligand that may act both as a donor (amino, NH2) and as an acceptor (cyanimino, N—CN). The N—H donor systems from both amino groups have close contacts to the nitrate anion [Fig. 2; hydrogen bond type (i)], and there is also hydrogen bonding between imino and amino N atoms of neighboring molecules [Fig. 2; hydrogen bond type (ii)]. In addition, there is intramolecular hydrogen bonding between amino and nitrile N atoms [Fig. 2; hydrogen bond type (iii)]. The above- mentioned three hydrogen-bonding modes have been reviewed for cnge coordination compounds by Hubberstey et al. (1997). The overall hydrogen bonding promotes the two-dimensional sheet structure and stabilizes the crystal architecture.

All three cnge molecules are planar within crystallographic resolution, and the maximum distances from the least-squares plane are 0.025 (N11—N16 ligand), 0.008 (N21—N26 ligand) and 0.013 (N31—N36 ligand) Å. The individual coordination does not severely affect the structural parameters of cnge (Fernanda et al., 1993). The shortest Ag—Ag distance along b is 3.648 (1) Å, parallel to the 21 axis. The structure as a whole consists of layers stacked along the b direction, which is also the direction of fast crystal growth.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP97 and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1990).

Figures top
[Figure 1] Fig. 1. ORTEP drawing of the title compound, with thermal ellipsoids scaled at the 50% probability level for non-H atoms.
[Figure 2] Fig. 2. Crystal packing for the title compound, showing the inter- and intra-molecular hydrogen bonding and hydrogen-bonding type.
Bis(cyanoguanidine)silver(I) nitrate cyanoguanidine top
Crystal data top
[Ag(C2H4N4)2](NO3)·C2H4N4F(000) = 840
Mr = 422.16Dx = 1.921 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9648 reflections
a = 15.526 (4) Åθ = 2.6–28.3°
b = 3.6482 (9) ŵ = 1.42 mm1
c = 25.797 (6) ÅT = 293 K
β = 92.519 (6)°Needle, colorless
V = 1459.8 (6) Å30.15 × 0.05 × 0.02 mm
Z = 4
Data collection top
Bruker AXS Apex CCD
diffractometer
3609 independent reflections
Radiation source: fine-focus sealed tube1818 reflections with I > \2s(I)
Graphite monochromatorRint = 0.095
ω scansθmax = 28.3°, θmin = 2.6°
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
h = 2020
Tmin = 0.746, Tmax = 0.989k = 44
9648 measured reflectionsl = 3422
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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.206Only H-atom coordinates refined
S = 0.87 w = 1/[σ2(Fo2)]
where P = (Fo2 + 2Fc2)/3
3609 reflections(Δ/σ)max < 0.001
245 parametersΔρmax = 0.78 e Å3
66 restraintsΔρmin = 0.53 e Å3
Crystal data top
[Ag(C2H4N4)2](NO3)·C2H4N4V = 1459.8 (6) Å3
Mr = 422.16Z = 4
Monoclinic, P21/nMo Kα radiation
a = 15.526 (4) ŵ = 1.42 mm1
b = 3.6482 (9) ÅT = 293 K
c = 25.797 (6) Å0.15 × 0.05 × 0.02 mm
β = 92.519 (6)°
Data collection top
Bruker AXS Apex CCD
diffractometer
3609 independent reflections
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
1818 reflections with I > \2s(I)
Tmin = 0.746, Tmax = 0.989Rint = 0.095
9648 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06566 restraints
wR(F2) = 0.206Only H-atom coordinates refined
S = 0.87Δρmax = 0.78 e Å3
3609 reflectionsΔρmin = 0.53 e Å3
245 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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ag0.24420 (4)0.5273 (2)0.18740 (2)0.0587 (3)
N110.1528 (4)0.5410 (17)0.2535 (2)0.0430 (15)
C120.0819 (5)0.6098 (19)0.2612 (2)0.0333 (16)
N130.0032 (4)0.6786 (18)0.2738 (2)0.0372 (14)
C140.0483 (5)0.838 (2)0.2380 (2)0.0357 (16)
N150.1313 (4)0.890 (2)0.2488 (3)0.0507 (18)
H110.161 (4)0.964 (19)0.225 (2)0.041 (7)*
H120.149 (4)0.81 (2)0.2746 (17)0.041 (7)*
N160.0243 (4)0.946 (2)0.1919 (2)0.0446 (16)
H130.024 (2)0.91 (2)0.184 (3)0.041 (7)*
H140.055 (4)1.051 (18)0.172 (3)0.041 (7)*
N210.3415 (4)0.5045 (19)0.1275 (3)0.0537 (18)
C220.3969 (4)0.5540 (19)0.0996 (3)0.0347 (16)
N230.4531 (4)0.5967 (16)0.0641 (2)0.0365 (14)
C240.5302 (4)0.7412 (19)0.0769 (2)0.0296 (14)
N250.5549 (4)0.843 (2)0.1242 (2)0.0436 (16)
H210.602 (2)0.916 (19)0.130 (3)0.041 (7)*
H220.524 (4)0.86 (2)0.147 (2)0.041 (7)*
N260.5843 (4)0.7850 (19)0.0396 (2)0.0382 (14)
H230.631 (2)0.868 (19)0.043 (3)0.041 (7)*
H240.567 (4)0.76 (2)0.0107 (13)0.041 (7)*
N310.1501 (4)1.0103 (18)0.1374 (2)0.0491 (17)
C320.1228 (5)1.0517 (19)0.0959 (3)0.0370 (16)
N330.0854 (4)1.0975 (17)0.0493 (2)0.0399 (15)
C340.1290 (4)1.256 (2)0.0112 (3)0.0322 (15)
N350.2099 (4)1.3840 (19)0.0187 (2)0.0426 (16)
H310.223 (5)1.473 (18)0.0077 (17)0.041 (7)*
H320.229 (5)1.39 (2)0.0474 (14)0.041 (7)*
N360.0908 (4)1.282 (2)0.0348 (2)0.0451 (16)
H330.111 (5)1.36 (2)0.0599 (19)0.041 (7)*
H340.045 (3)1.19 (2)0.037 (3)0.041 (7)*
O10.8457 (3)0.3640 (16)0.1292 (2)0.0503 (14)
O20.7356 (4)0.0943 (15)0.1616 (2)0.0502 (14)
N0.7724 (4)0.2361 (17)0.1239 (2)0.0370 (14)
O30.7329 (3)0.2463 (19)0.08107 (19)0.0556 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag0.0399 (4)0.0991 (7)0.0378 (4)0.0049 (4)0.0106 (2)0.0029 (3)
N110.036 (3)0.046 (4)0.048 (4)0.004 (3)0.009 (3)0.013 (3)
C120.036 (4)0.043 (4)0.021 (3)0.011 (3)0.005 (3)0.002 (3)
N130.031 (3)0.050 (4)0.031 (3)0.006 (3)0.004 (2)0.007 (3)
C140.037 (4)0.043 (4)0.027 (3)0.002 (3)0.005 (3)0.001 (3)
N150.034 (3)0.077 (6)0.042 (4)0.001 (3)0.005 (3)0.018 (3)
N160.041 (4)0.063 (5)0.030 (3)0.005 (4)0.007 (3)0.010 (3)
N210.045 (4)0.065 (5)0.052 (4)0.005 (4)0.013 (3)0.000 (3)
C220.034 (4)0.038 (4)0.031 (3)0.005 (3)0.003 (3)0.001 (3)
N230.031 (3)0.047 (4)0.032 (3)0.010 (3)0.003 (2)0.007 (2)
C240.037 (4)0.028 (4)0.024 (3)0.002 (3)0.002 (3)0.001 (3)
N250.035 (4)0.063 (5)0.034 (3)0.013 (3)0.007 (3)0.014 (3)
N260.028 (3)0.055 (4)0.031 (3)0.010 (3)0.004 (3)0.002 (3)
N310.050 (4)0.061 (5)0.036 (3)0.010 (3)0.002 (3)0.007 (3)
C320.031 (3)0.034 (4)0.046 (4)0.004 (3)0.009 (3)0.004 (3)
N330.035 (3)0.050 (4)0.034 (3)0.011 (3)0.001 (3)0.015 (3)
C340.031 (3)0.027 (4)0.039 (4)0.002 (3)0.004 (3)0.005 (3)
N350.042 (4)0.049 (4)0.037 (3)0.009 (3)0.001 (3)0.002 (3)
N360.040 (4)0.064 (5)0.030 (3)0.006 (4)0.003 (3)0.008 (3)
O10.037 (3)0.065 (4)0.048 (3)0.015 (3)0.006 (2)0.008 (3)
O20.047 (3)0.063 (4)0.042 (3)0.006 (3)0.010 (2)0.013 (2)
N0.039 (3)0.037 (4)0.035 (3)0.002 (3)0.002 (3)0.007 (3)
O30.042 (3)0.082 (5)0.042 (3)0.022 (3)0.009 (3)0.012 (3)
Geometric parameters (Å, º) top
Ag—N212.210 (7)N25—H210.79 (2)
Ag—N112.266 (6)N25—H220.78 (2)
Ag—N312.596 (7)N26—H230.79 (2)
N11—C121.155 (9)N26—H240.79 (2)
C12—N131.302 (9)N31—C321.144 (9)
N13—C141.328 (8)C32—N331.323 (9)
C14—N161.322 (9)N33—C341.350 (8)
C14—N151.344 (9)C34—N361.307 (9)
N15—H110.79 (2)C34—N351.345 (9)
N15—H120.79 (2)N35—H310.79 (2)
N16—H130.79 (2)N35—H320.79 (2)
N16—H140.79 (2)N36—H330.79 (2)
N21—C221.159 (9)N36—H340.79 (2)
C22—N231.301 (9)O1—N1.233 (7)
N23—C241.336 (8)O2—N1.260 (7)
C24—N261.314 (8)N—O31.239 (7)
C24—N251.318 (8)
N21—Ag—N11175.5 (2)C24—N25—H21120 (6)
N21—Ag—N3193.8 (2)C24—N25—H22125 (6)
N11—Ag—N3190.1 (2)H21—N25—H22115 (8)
C12—N11—Ag140.2 (5)C24—N26—H23125 (6)
N11—C12—N13175.4 (7)C24—N26—H24118 (5)
C12—N13—C14117.1 (6)H23—N26—H24116 (8)
N16—C14—N13124.8 (7)C32—N31—Ag137.0 (6)
N16—C14—N15117.1 (7)N31—C32—N33175.7 (8)
N13—C14—N15118.1 (6)C32—N33—C34120.2 (6)
C14—N15—H11115 (6)N36—C34—N35119.3 (7)
C14—N15—H12120 (6)N36—C34—N33118.1 (6)
H11—N15—H12124 (8)N35—C34—N33122.6 (6)
C14—N16—H13119 (6)C34—N35—H31107 (6)
C14—N16—H14123 (6)C34—N35—H32118 (6)
H13—N16—H14118 (8)H31—N35—H32134 (8)
C22—N21—Ag167.6 (6)C34—N36—H33126 (6)
N21—C22—N23173.5 (7)C34—N36—H34115 (6)
C22—N23—C24119.7 (6)H33—N36—H34119 (8)
N26—C24—N25118.3 (6)O1—N—O3120.4 (6)
N26—C24—N23117.5 (6)O1—N—O2121.1 (6)
N25—C24—N23124.1 (6)O3—N—O2118.5 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N15—H11···O2i0.79 (2)2.30 (3)3.079 (9)169 (8)
N15—H12···O2ii0.79 (2)2.31 (3)3.075 (8)165 (7)
N16—H13···N310.79 (2)2.37 (4)3.113 (9)157 (7)
N16—H14···O1i0.79 (2)2.18 (3)2.954 (8)170 (8)
N25—H21···O2iii0.79 (2)2.29 (3)3.067 (8)170 (8)
N25—H21···O3iii0.79 (2)2.72 (5)3.363 (8)140 (7)
N25—H22···N13ii0.78 (2)2.39 (5)3.073 (8)146 (7)
N26—H23···O3iii0.79 (2)2.29 (4)3.014 (8)154 (7)
N26—H24···N23iv0.79 (2)2.34 (5)3.048 (8)151 (8)
N35—H31···O3v0.79 (2)2.28 (3)3.071 (8)176 (8)
N35—H32···N21iii0.79 (2)2.68 (4)3.427 (10)160 (7)
N36—H33···O1v0.79 (2)2.17 (3)2.962 (8)173 (8)
N36—H34···N33vi0.79 (2)2.29 (3)3.075 (9)176 (8)
Symmetry codes: (i) x1, y+1, z; (ii) x+1/2, y+1/2, z+1/2; (iii) x, y+1, z; (iv) x+1, y+1, z; (v) x+1, y+2, z; (vi) x, y+2, z.

Experimental details

Crystal data
Chemical formula[Ag(C2H4N4)2](NO3)·C2H4N4
Mr422.16
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)15.526 (4), 3.6482 (9), 25.797 (6)
β (°) 92.519 (6)
V3)1459.8 (6)
Z4
Radiation typeMo Kα
µ (mm1)1.42
Crystal size (mm)0.15 × 0.05 × 0.02
Data collection
DiffractometerBruker AXS Apex CCD
diffractometer
Absorption correctionEmpirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.746, 0.989
No. of measured, independent and
observed [I > \2s(I)] reflections
9648, 3609, 1818
Rint0.095
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.065, 0.206, 0.87
No. of reflections3609
No. of parameters245
No. of restraints66
H-atom treatmentOnly H-atom coordinates refined
Δρmax, Δρmin (e Å3)0.78, 0.53

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP97 and PLATON (Spek, 2003), SHELXL97 (Sheldrick, 1990).

Selected geometric parameters (Å, º) top
Ag—N212.210 (7)C22—N231.301 (9)
Ag—N112.266 (6)N23—C241.336 (8)
Ag—N312.596 (7)C24—N261.314 (8)
N11—C121.155 (9)C24—N251.318 (8)
C12—N131.302 (9)N31—C321.144 (9)
N13—C141.328 (8)C32—N331.323 (9)
C14—N161.322 (9)N33—C341.350 (8)
C14—N151.344 (9)C34—N361.307 (9)
N21—C221.159 (9)C34—N351.345 (9)
N21—Ag—N11175.5 (2)C22—N23—C24119.7 (6)
N21—Ag—N3193.8 (2)N26—C24—N25118.3 (6)
N11—Ag—N3190.1 (2)N26—C24—N23117.5 (6)
C12—N11—Ag140.2 (5)N25—C24—N23124.1 (6)
N11—C12—N13175.4 (7)C32—N31—Ag137.0 (6)
C12—N13—C14117.1 (6)N31—C32—N33175.7 (8)
N16—C14—N13124.8 (7)C32—N33—C34120.2 (6)
N16—C14—N15117.1 (7)N36—C34—N35119.3 (7)
N13—C14—N15118.1 (6)N36—C34—N33118.1 (6)
C22—N21—Ag167.6 (6)N35—C34—N33122.6 (6)
N21—C22—N23173.5 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N15—H11···O2i0.79 (2)2.30 (3)3.079 (9)169 (8)
N15—H12···O2ii0.79 (2)2.31 (3)3.075 (8)165 (7)
N16—H13···N310.79 (2)2.37 (4)3.113 (9)157 (7)
N16—H14···O1i0.79 (2)2.18 (3)2.954 (8)170 (8)
N25—H21···O2iii0.79 (2)2.29 (3)3.067 (8)170 (8)
N25—H21···O3iii0.79 (2)2.72 (5)3.363 (8)140 (7)
N25—H22···N13ii0.78 (2)2.39 (5)3.073 (8)146 (7)
N26—H23···O3iii0.79 (2)2.29 (4)3.014 (8)154 (7)
N26—H24···N23iv0.79 (2)2.34 (5)3.048 (8)151 (8)
N35—H31···O3v0.79 (2)2.28 (3)3.071 (8)176 (8)
N35—H32···N21iii0.79 (2)2.68 (4)3.427 (10)160 (7)
N36—H33···O1v0.79 (2)2.17 (3)2.962 (8)173 (8)
N36—H34···N33vi0.79 (2)2.29 (3)3.075 (9)176 (8)
Symmetry codes: (i) x1, y+1, z; (ii) x+1/2, y+1/2, z+1/2; (iii) x, y+1, z; (iv) x+1, y+1, z; (v) x+1, y+2, z; (vi) x, y+2, z.
 

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