Bis(2,5-di-4-pyridyl-1,3,4-oxadiazole)­silver(I) nitrate monohydrate

Zhang, Z.-H.; Li, C.-P.; Tian, Y.-L.; Guo, Y.-M.

doi:10.1107/S1600536807057546

Bis(2,5-di-4-pyridyl-1,3,4-oxadiazole)silver(I) nitrate monohydrate

Z.-H. Zhang, C.-P. Li, Y.-L. Tian and Y.-M. Guo

In the title mononuclear complex, [Ag(C₁₂H₈N₄O)₂]NO₃·H₂O, the Ag^I ion is coordinated linearly by two pyridyl N atoms from two crystallographically independent monodentate 2,5-di-4-pyridyl-1,3,4-oxadiazole (4-bpo) ligands. In addition, the asymmetric unit contains one nitrate anion and one solvent water molecule. In the crystal structure, nitrate anions connect to Ag^I ions via weak Ag

O interactions [Ag

O = 2.836 (3) Å] and to two symmetry-related solvent water molecules via O—H

O hydrogen bonds, to afford a one-dimensional herring-bone-like motif along [100]. Significant π–π stacking interactions [Cg

Cg = 3.614 (2)–3.721 (2) Å, where Cg is the centroid of a pyridyl or oxadiazole ring] are also found between two adjacent one-dimensional motifs, resulting in a double-strand supramolecular array.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807057546/lh2554sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807057546/lh2554Isup2.hkl Contains datablock I

CCDC reference: 672678

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.004 Å
R factor = 0.031
wR factor = 0.085
Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.09
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        Ag1
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N9

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      1.087
            Tmax scaled      0.923 Tmin scaled      0.849
PLAT794_ALERT_5_G Check Predicted Bond Valency for Ag1         (9)       0.84

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

The angular dipyridyl ligand, 2,5-di-4-pyridyl-1,3,4-oxadiazole (4-bpo), has been demonstrated to be an excellent building block to assemble with familiar transition metal ions, which produces a variety of coordination complexes from 0-D to 3-D (Du et al., 2005, 2006, 2007). With respect to Ag^I complexes, these are usually coordination polymers with infinite coordination arrays, in which the 4-bpo ligands display either µ-N_py, N_py or µ₃-N_py, N_py, N_oxadiazole bridging coordination modes (Dong et al., 2003; Du & Zhao, 2004). For instance, self-assembly of AgNO₃ with 4-bpo through slow diffusion in CH₃CN/CHCl₃ yields a chain complex [Ag(4-bpo)(NO₃)], in which the trigonal Ag^I centers are bridged by 4-bpo in µ-N_py, N_py fashion (Guo et al., 2003). Herein, we describe a related complex [Ag(4-bpo)₂](NO₃)(H₂O) (I) prepared under hydrothermal condition, which has an unexpected mononuclear structure.

The molecular structure of the title compound (I) is shown in Fig. 1. The Ag^I ion is coordinated by two N atoms of the pyridyl rings from two separate monodentate 4-bpo ligands in trans-arrangement [Ag1—N1 = 2.171 (2) Å and Ag1—N5 = 2.173 (2) Å], displaying a linear geometry [N1—Ag1—N5 = 179.10 (8)°]. There is also a weak Ag1—O5 (2.836 (3) Å) contact between each Ag^I center and the adjacent nitrate anion. The two pyridyl rings in one 4-bpo ligand are inclined by 7.9 (4) and 12.7 (4)° with respect to the central oxadiazole plane, and by 10.6 (1)° with respect to each other. Corresponding values for the other 4-bpo molecule are 5.9 (2), 13.3 (1), and 10.7 (2)°. Interestingly, each nitrate acts as the acceptor of a pair of O—H···O bonds with the neighboring two water molecules, and thus, a supramolecular chain along the [100] direction is afforded. Two adjacent such 1-D chains are interdigitated and further combined to give a double-strand supramolecular array (see Fig. 2), via interchain parallel π–π stacking forces (center-to-center distances between the corresponding aromatic rings in 4-bpo are in the range of 3.61–3.72 Å). In addition, multiple C—H···O and C—H···N interactions (see Table) are observed to consolidate this crystalline lattice.

Related literature top

For related literature, see: Dong et al. (2003); Du & Zhao (2004); Du et al. (2005, 2006, 2007); Guo et al. (2003).

Experimental top

A water (8 ml) solution containing AgNO₃ (17.3 mg, 0.1 mmol), 4-bpo (11.2 mg, 0.05 mmol), and oxamide (9.0 mg, 0.1 mmol) was sealed in a Teflon-lined stainless steel vessel (20 ml), which was heated to 373 K for 24 h and subsequently cooled to room temperature at a rate of 1 K/h. Colorless block shape crystals were obtained in 75% yield (11.9 mg, based on 4-bpo). IR (cm^-1): 3385b, 2362s, 1654s, 1563m, 1536m, 1484m, 1416m, 1384vs, 1106m, 988w, 832m, 741w, 713s, 637w.

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: APEX2 (Bruker, 2003) and SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001) and DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures top

	Fig. 1. Molecular structure of with atom labeling of all non-H atoms, shown with 30% probability displacement ellipsoids.
	Fig. 2. One-dimensional double-strand supramolecular array of (I) extending along the [100] direction. H atoms of 4-bpo are omitted for clarity. Hydrogen bonds are shown with dashed lines.

s(2,5-di-4-pyridyl-1,3,4-oxadiazole)silver(I) nitrate monohydrate top

Crystal data top

[Ag(C₁₂H₈N₄O)₂]NO₃·H₂O	F(000) = 1280
M_r = 636.34	D_x = 1.741 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4561 reflections
a = 7.3200 (19) Å	θ = 2.2–25.8°
b = 13.281 (3) Å	µ = 0.89 mm⁻¹
c = 25.002 (6) Å	T = 294 K
β = 92.664 (3)°	Block, colourless
V = 2428.0 (11) Å³	0.14 × 0.13 × 0.09 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	4287 independent reflections
Radiation source: fine-focus sealed tube	3232 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→7
T_min = 0.781, T_max = 0.849	k = −15→15
13051 measured reflections	l = −29→29

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0405P)² + 1.1166P] where P = (F_o² + 2F_c²)/3
4287 reflections	(Δ/σ)_max = 0.001
361 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

[Ag(C₁₂H₈N₄O)₂]NO₃·H₂O	V = 2428.0 (11) Å³
M_r = 636.34	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.3200 (19) Å	µ = 0.89 mm⁻¹
b = 13.281 (3) Å	T = 294 K
c = 25.002 (6) Å	0.14 × 0.13 × 0.09 mm
β = 92.664 (3)°

Data collection top

Bruker APEXII CCD diffractometer	4287 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3232 reflections with I > 2σ(I)
T_min = 0.781, T_max = 0.849	R_int = 0.021
13051 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 1.02	Δρ_max = 0.50 e Å⁻³
4287 reflections	Δρ_min = −0.39 e Å⁻³
361 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

	x	y	z	U_iso*/U_eq
Ag1	0.75772 (4)	0.494095 (15)	0.003989 (9)	0.06022 (12)
O1	0.7828 (2)	0.01648 (12)	0.14056 (6)	0.0331 (4)
O2	0.7228 (2)	0.96348 (13)	−0.13712 (6)	0.0353 (4)
O3	0.3960 (5)	0.5442 (2)	0.15393 (12)	0.0977 (9)
O4	0.6848 (4)	0.5320 (2)	0.14858 (12)	0.0962 (9)
O5	0.5187 (5)	0.5726 (2)	0.07974 (11)	0.1103 (11)
N1	0.7338 (3)	0.34138 (15)	0.03382 (8)	0.0400 (5)
N2	0.6208 (3)	−0.03195 (16)	0.06841 (8)	0.0390 (5)
N3	0.6508 (3)	−0.11581 (15)	0.10182 (8)	0.0394 (5)
N4	0.9379 (4)	−0.26272 (19)	0.27527 (9)	0.0542 (6)
N5	0.7790 (3)	0.64634 (16)	−0.02698 (9)	0.0422 (5)
N6	0.8743 (3)	1.02181 (15)	−0.06527 (8)	0.0385 (5)
N7	0.8432 (3)	1.10181 (16)	−0.10126 (8)	0.0403 (5)
N8	0.5575 (4)	1.2125 (2)	−0.28380 (10)	0.0635 (8)
N9	0.5326 (5)	0.55187 (18)	0.12635 (12)	0.0624 (8)
C1	0.7127 (3)	0.14629 (17)	0.07331 (9)	0.0294 (5)
C2	0.7864 (3)	0.22346 (18)	0.10502 (9)	0.0351 (6)
H2	0.8297	0.2108	0.1399	0.042*
C3	0.7942 (4)	0.31880 (19)	0.08386 (10)	0.0402 (6)
H3	0.8437	0.3701	0.1053	0.048*
C4	0.6629 (4)	0.26646 (19)	0.00361 (10)	0.0391 (6)
H4	0.6216	0.2810	−0.0313	0.047*
C5	0.6482 (4)	0.16930 (18)	0.02156 (9)	0.0354 (6)
H5	0.5960	0.1197	−0.0005	0.042*
C6	0.7006 (3)	0.04297 (18)	0.09256 (9)	0.0315 (6)
C7	0.7458 (3)	−0.08427 (18)	0.14297 (10)	0.0331 (6)
C8	0.8143 (4)	−0.14296 (19)	0.18910 (10)	0.0359 (6)
C9	0.8063 (4)	−0.2469 (2)	0.18619 (11)	0.0457 (7)
H9	0.7597	−0.2788	0.1554	0.055*
C10	0.8688 (4)	−0.3024 (2)	0.22991 (12)	0.0535 (8)
H10	0.8621	−0.3722	0.2275	0.064*
C11	0.9429 (4)	−0.1626 (2)	0.27713 (11)	0.0508 (8)
H11	0.9894	−0.1329	0.3086	0.061*
C12	0.8842 (4)	−0.0996 (2)	0.23588 (10)	0.0426 (7)
H12	0.8917	−0.0300	0.2395	0.051*
C13	0.7920 (3)	0.84052 (18)	−0.06722 (9)	0.0319 (6)
C14	0.7207 (4)	0.76235 (19)	−0.09872 (10)	0.0378 (6)
H14	0.6758	0.7742	−0.1336	0.045*
C15	0.7181 (4)	0.66720 (19)	−0.07716 (11)	0.0430 (7)
H15	0.6719	0.6148	−0.0984	0.052*
C16	0.8458 (4)	0.72245 (19)	0.00307 (10)	0.0399 (6)
H16	0.8871	0.7089	0.0381	0.048*
C17	0.8562 (4)	0.81970 (18)	−0.01540 (9)	0.0363 (6)
H17	0.9053	0.8705	0.0065	0.044*
C18	0.8010 (3)	0.94280 (18)	−0.08788 (9)	0.0324 (6)
C19	0.7541 (4)	1.06397 (18)	−0.14211 (10)	0.0348 (6)
C20	0.6850 (4)	1.1144 (2)	−0.19096 (10)	0.0379 (6)
C21	0.6799 (4)	1.2186 (2)	−0.19361 (11)	0.0467 (7)
H21	0.7187	1.2576	−0.1643	0.056*
C22	0.6162 (5)	1.2629 (3)	−0.24038 (13)	0.0594 (8)
H22	0.6138	1.3328	−0.2418	0.071*
C23	0.5636 (5)	1.1129 (3)	−0.28027 (12)	0.0640 (9)
H23	0.5237	1.0761	−0.3102	0.077*
C24	0.6249 (4)	1.0599 (2)	−0.23536 (11)	0.0510 (7)
H24	0.6255	0.9899	−0.2351	0.061*
O6	0.0299 (5)	0.5615 (2)	0.09432 (11)	0.1088 (10)
H6A	−0.0340	0.5408	0.1197	0.163*
H6B	0.1381	0.5810	0.1026	0.163*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0852 (2)	0.03234 (14)	0.06241 (18)	−0.00484 (12)	−0.00465 (14)	0.01112 (10)
O1	0.0375 (10)	0.0287 (9)	0.0324 (9)	−0.0012 (7)	−0.0035 (7)	0.0006 (7)
O2	0.0401 (11)	0.0334 (9)	0.0318 (9)	−0.0022 (8)	−0.0060 (8)	−0.0008 (7)
O3	0.118 (3)	0.0802 (19)	0.096 (2)	0.0038 (18)	0.0234 (19)	−0.0079 (16)
O4	0.106 (2)	0.0663 (16)	0.112 (2)	−0.0123 (16)	−0.0351 (19)	0.0043 (15)
O5	0.159 (3)	0.108 (2)	0.0636 (18)	0.023 (2)	−0.0036 (18)	0.0261 (16)
N1	0.0477 (15)	0.0320 (11)	0.0396 (12)	−0.0005 (10)	−0.0035 (10)	0.0025 (9)
N2	0.0454 (14)	0.0339 (11)	0.0370 (12)	−0.0049 (10)	−0.0072 (10)	0.0031 (9)
N3	0.0457 (15)	0.0327 (11)	0.0392 (12)	−0.0059 (10)	−0.0039 (10)	0.0039 (9)
N4	0.0566 (17)	0.0581 (16)	0.0474 (14)	0.0071 (13)	−0.0035 (12)	0.0134 (12)
N5	0.0515 (15)	0.0339 (11)	0.0409 (13)	−0.0007 (11)	−0.0010 (11)	0.0034 (9)
N6	0.0443 (14)	0.0330 (11)	0.0372 (12)	−0.0028 (10)	−0.0074 (10)	0.0013 (9)
N7	0.0482 (15)	0.0330 (11)	0.0389 (12)	−0.0030 (10)	−0.0073 (11)	0.0021 (9)
N8	0.0556 (18)	0.086 (2)	0.0479 (16)	0.0098 (15)	−0.0030 (13)	0.0239 (14)
N9	0.088 (2)	0.0349 (14)	0.0635 (19)	−0.0041 (15)	−0.0099 (18)	−0.0045 (12)
C1	0.0263 (14)	0.0315 (12)	0.0305 (13)	0.0004 (10)	0.0014 (10)	−0.0017 (9)
C2	0.0388 (16)	0.0366 (13)	0.0294 (12)	0.0001 (12)	−0.0038 (11)	−0.0026 (10)
C3	0.0475 (18)	0.0313 (13)	0.0413 (15)	−0.0042 (12)	−0.0023 (12)	−0.0060 (11)
C4	0.0459 (17)	0.0374 (14)	0.0335 (13)	0.0001 (13)	−0.0045 (12)	0.0025 (11)
C5	0.0389 (16)	0.0347 (13)	0.0320 (13)	−0.0014 (11)	−0.0035 (11)	−0.0040 (10)
C6	0.0307 (15)	0.0353 (13)	0.0282 (12)	−0.0004 (11)	−0.0001 (10)	−0.0012 (10)
C7	0.0340 (15)	0.0300 (13)	0.0354 (13)	−0.0021 (11)	0.0032 (11)	−0.0004 (10)
C8	0.0343 (15)	0.0387 (14)	0.0347 (13)	0.0006 (12)	0.0013 (11)	0.0054 (11)
C9	0.0520 (19)	0.0383 (14)	0.0459 (16)	−0.0030 (13)	−0.0073 (13)	0.0036 (12)
C10	0.059 (2)	0.0407 (15)	0.0601 (19)	0.0021 (15)	−0.0047 (16)	0.0110 (14)
C11	0.055 (2)	0.062 (2)	0.0354 (15)	0.0054 (16)	−0.0038 (13)	0.0010 (13)
C12	0.0473 (18)	0.0419 (15)	0.0384 (15)	0.0025 (13)	−0.0013 (13)	0.0002 (11)
C13	0.0296 (15)	0.0342 (13)	0.0319 (13)	0.0024 (11)	0.0006 (11)	−0.0002 (10)
C14	0.0420 (17)	0.0382 (14)	0.0325 (13)	−0.0034 (12)	−0.0051 (12)	−0.0018 (10)
C15	0.0513 (18)	0.0340 (14)	0.0431 (15)	−0.0065 (13)	−0.0042 (13)	−0.0060 (11)
C16	0.0469 (18)	0.0400 (14)	0.0323 (13)	0.0025 (13)	−0.0034 (12)	0.0033 (11)
C17	0.0397 (16)	0.0359 (13)	0.0331 (13)	−0.0021 (12)	−0.0019 (11)	−0.0051 (10)
C18	0.0298 (15)	0.0357 (14)	0.0315 (13)	0.0000 (11)	−0.0016 (11)	−0.0033 (10)
C19	0.0357 (16)	0.0336 (13)	0.0350 (14)	−0.0002 (11)	0.0013 (12)	0.0023 (10)
C20	0.0318 (15)	0.0475 (15)	0.0341 (14)	0.0018 (12)	0.0004 (11)	0.0041 (11)
C21	0.0520 (19)	0.0447 (16)	0.0436 (15)	0.0025 (14)	0.0017 (13)	0.0073 (12)
C22	0.057 (2)	0.063 (2)	0.058 (2)	0.0065 (17)	0.0033 (16)	0.0220 (16)
C23	0.060 (2)	0.093 (3)	0.0373 (17)	0.0018 (19)	−0.0141 (15)	0.0005 (16)
C24	0.054 (2)	0.0558 (18)	0.0427 (16)	0.0007 (15)	−0.0102 (14)	−0.0016 (13)
O6	0.129 (3)	0.121 (3)	0.0761 (19)	0.025 (2)	−0.0020 (18)	−0.0038 (17)

Geometric parameters (Å, º) top

Ag1—N1	2.171 (2)	C5—H5	0.9300
Ag1—N5	2.173 (2)	C7—C8	1.461 (3)
O1—C6	1.364 (3)	C8—C12	1.381 (4)
O1—C7	1.367 (3)	C8—C9	1.384 (4)
O2—C19	1.361 (3)	C9—C10	1.378 (4)
O2—C18	1.361 (3)	C9—H9	0.9300
O3—N9	1.245 (4)	C10—H10	0.9300
O4—N9	1.250 (4)	C11—C12	1.381 (4)
O5—N9	1.197 (3)	C11—H11	0.9300
N1—C4	1.339 (3)	C12—H12	0.9300
N1—C3	1.341 (3)	C13—C17	1.385 (3)
N2—C6	1.289 (3)	C13—C14	1.390 (3)
N2—N3	1.403 (3)	C13—C18	1.456 (3)
N3—C7	1.285 (3)	C14—C15	1.374 (4)
N4—C10	1.329 (4)	C14—H14	0.9300
N4—C11	1.331 (4)	C15—H15	0.9300
N5—C16	1.338 (3)	C16—C17	1.375 (3)
N5—C15	1.341 (3)	C16—H16	0.9300
N6—C18	1.296 (3)	C17—H17	0.9300
N6—N7	1.404 (3)	C19—C20	1.462 (3)
N7—C19	1.288 (3)	C20—C24	1.380 (4)
N8—C23	1.327 (4)	C20—C21	1.386 (4)
N8—C22	1.329 (4)	C21—C22	1.371 (4)
C1—C2	1.389 (3)	C21—H21	0.9300
C1—C5	1.391 (3)	C22—H22	0.9300
C1—C6	1.458 (3)	C23—C24	1.383 (4)
C2—C3	1.375 (3)	C23—H23	0.9300
C2—H2	0.9300	C24—H24	0.9300
C3—H3	0.9300	O6—H6A	0.8505
C4—C5	1.372 (3)	O6—H6B	0.8501
C4—H4	0.9300

N1—Ag1—N5	179.10 (8)	N4—C10—H10	117.8
C6—O1—C7	102.18 (18)	C9—C10—H10	117.8
C19—O2—C18	102.44 (18)	N4—C11—C12	124.9 (3)
C4—N1—C3	117.5 (2)	N4—C11—H11	117.5
C4—N1—Ag1	122.40 (17)	C12—C11—H11	117.5
C3—N1—Ag1	120.05 (17)	C8—C12—C11	118.0 (3)
C6—N2—N3	106.20 (19)	C8—C12—H12	121.0
C7—N3—N2	106.4 (2)	C11—C12—H12	121.0
C10—N4—C11	115.8 (2)	C17—C13—C14	118.9 (2)
C16—N5—C15	117.8 (2)	C17—C13—C18	119.9 (2)
C16—N5—Ag1	122.21 (17)	C14—C13—C18	121.2 (2)
C15—N5—Ag1	119.95 (17)	C15—C14—C13	118.4 (2)
C18—N6—N7	106.34 (19)	C15—C14—H14	120.8
C19—N7—N6	105.9 (2)	C13—C14—H14	120.8
C23—N8—C22	116.0 (3)	N5—C15—C14	123.2 (2)
O5—N9—O3	121.6 (4)	N5—C15—H15	118.4
O5—N9—O4	121.0 (4)	C14—C15—H15	118.4
O3—N9—O4	117.3 (3)	N5—C16—C17	123.0 (2)
C2—C1—C5	118.3 (2)	N5—C16—H16	118.5
C2—C1—C6	122.3 (2)	C17—C16—H16	118.5
C5—C1—C6	119.4 (2)	C16—C17—C13	118.7 (2)
C3—C2—C1	118.8 (2)	C16—C17—H17	120.7
C3—C2—H2	120.6	C13—C17—H17	120.7
C1—C2—H2	120.6	N6—C18—O2	112.3 (2)
N1—C3—C2	123.2 (2)	N6—C18—C13	128.7 (2)
N1—C3—H3	118.4	O2—C18—C13	119.0 (2)
C2—C3—H3	118.4	N7—C19—O2	113.0 (2)
N1—C4—C5	123.3 (2)	N7—C19—C20	128.8 (2)
N1—C4—H4	118.4	O2—C19—C20	118.2 (2)
C5—C4—H4	118.4	C24—C20—C21	118.6 (3)
C4—C5—C1	118.9 (2)	C24—C20—C19	121.1 (2)
C4—C5—H5	120.6	C21—C20—C19	120.3 (2)
C1—C5—H5	120.6	C22—C21—C20	118.4 (3)
N2—C6—O1	112.6 (2)	C22—C21—H21	120.8
N2—C6—C1	127.2 (2)	C20—C21—H21	120.8
O1—C6—C1	120.1 (2)	N8—C22—C21	124.4 (3)
N3—C7—O1	112.6 (2)	N8—C22—H22	117.8
N3—C7—C8	127.7 (2)	C21—C22—H22	117.8
O1—C7—C8	119.7 (2)	N8—C23—C24	124.8 (3)
C12—C8—C9	118.3 (2)	N8—C23—H23	117.6
C12—C8—C7	123.1 (2)	C24—C23—H23	117.6
C9—C8—C7	118.6 (2)	C20—C24—C23	117.7 (3)
C10—C9—C8	118.7 (3)	C20—C24—H24	121.1
C10—C9—H9	120.7	C23—C24—H24	121.1
C8—C9—H9	120.7	H6A—O6—H6B	117.1
N4—C10—C9	124.4 (3)

C6—N2—N3—C7	−0.1 (3)	N4—C11—C12—C8	0.3 (5)
C18—N6—N7—C19	0.1 (3)	C17—C13—C14—C15	−0.5 (4)
C5—C1—C2—C3	−0.6 (4)	C18—C13—C14—C15	179.2 (2)
C6—C1—C2—C3	179.6 (2)	C16—N5—C15—C14	−0.2 (4)
C4—N1—C3—C2	0.0 (4)	Ag1—N5—C15—C14	177.4 (2)
Ag1—N1—C3—C2	−178.8 (2)	C13—C14—C15—N5	0.8 (4)
C1—C2—C3—N1	0.0 (4)	C15—N5—C16—C17	−0.7 (4)
C3—N1—C4—C5	0.6 (4)	Ag1—N5—C16—C17	−178.3 (2)
Ag1—N1—C4—C5	179.4 (2)	N5—C16—C17—C13	1.0 (4)
N1—C4—C5—C1	−1.2 (4)	C14—C13—C17—C16	−0.4 (4)
C2—C1—C5—C4	1.2 (4)	C18—C13—C17—C16	179.9 (2)
C6—C1—C5—C4	−179.0 (2)	N7—N6—C18—O2	0.4 (3)
N3—N2—C6—O1	−0.3 (3)	N7—N6—C18—C13	−178.9 (2)
N3—N2—C6—C1	178.2 (2)	C19—O2—C18—N6	−0.7 (3)
C7—O1—C6—N2	0.6 (3)	C19—O2—C18—C13	178.7 (2)
C7—O1—C6—C1	−178.1 (2)	C17—C13—C18—N6	5.0 (4)
C2—C1—C6—N2	173.4 (3)	C14—C13—C18—N6	−174.7 (3)
C5—C1—C6—N2	−6.4 (4)	C17—C13—C18—O2	−174.3 (2)
C2—C1—C6—O1	−8.2 (4)	C14—C13—C18—O2	6.1 (4)
C5—C1—C6—O1	172.0 (2)	N6—N7—C19—O2	−0.5 (3)
N2—N3—C7—O1	0.5 (3)	N6—N7—C19—C20	179.2 (3)
N2—N3—C7—C8	−179.2 (2)	C18—O2—C19—N7	0.7 (3)
C6—O1—C7—N3	−0.6 (3)	C18—O2—C19—C20	−179.0 (2)
C6—O1—C7—C8	179.1 (2)	N7—C19—C20—C24	166.7 (3)
N3—C7—C8—C12	−167.0 (3)	O2—C19—C20—C24	−13.6 (4)
O1—C7—C8—C12	13.3 (4)	N7—C19—C20—C21	−12.8 (4)
N3—C7—C8—C9	12.0 (4)	O2—C19—C20—C21	166.9 (2)
O1—C7—C8—C9	−167.7 (2)	C24—C20—C21—C22	−0.4 (4)
C12—C8—C9—C10	−0.2 (4)	C19—C20—C21—C22	179.2 (3)
C7—C8—C9—C10	−179.2 (3)	C23—N8—C22—C21	−0.3 (5)
C11—N4—C10—C9	0.7 (5)	C20—C21—C22—N8	0.3 (5)
C8—C9—C10—N4	−0.3 (5)	C22—N8—C23—C24	0.3 (5)
C10—N4—C11—C12	−0.7 (5)	C21—C20—C24—C23	0.4 (4)
C9—C8—C12—C11	0.2 (4)	C19—C20—C24—C23	−179.2 (3)
C7—C8—C12—C11	179.2 (3)	N8—C23—C24—C20	−0.3 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O4ⁱ	0.85	2.22	2.949 (5)	144
O6—H6B···O3	0.85	2.29	3.014 (5)	144
C4—H4···O5ⁱⁱ	0.93	2.49	3.228 (4)	137
C5—H5···N2ⁱⁱⁱ	0.93	2.55	3.443 (3)	161
C9—H9···O4^iv	0.93	2.58	3.197 (4)	125
C15—H15···O3ⁱⁱ	0.93	2.56	3.481 (4)	169
C17—H17···N6^v	0.93	2.57	3.467 (3)	163

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

Experimental details

Crystal data
Chemical formula	[Ag(C₁₂H₈N₄O)₂]NO₃·H₂O
M_r	636.34
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	7.3200 (19), 13.281 (3), 25.002 (6)
β (°)	92.664 (3)
V (Å³)	2428.0 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.89
Crystal size (mm)	0.14 × 0.13 × 0.09

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.781, 0.849
No. of measured, independent and observed [I > 2σ(I)] reflections	13051, 4287, 3232
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.085, 1.02
No. of reflections	4287
No. of parameters	361
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.39

Computer programs: , APEX2 (Bruker, 2003) and SAINT (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001) and DIAMOND (Brandenburg, 2005), SHELXTL (Bruker, 2001).

Selected geometric parameters (Å, º) top

Ag1—N1	2.171 (2)	Ag1—N5	2.173 (2)

N1—Ag1—N5	179.10 (8)