catena-Poly[ammonium [aqua­bis­(μ-2,3,5,6-tetra­oxo-4-nitro­pyridin-4-ido)argentate(I)]]

In the title compound, {(NH₄)[Ag(C₅HN₂O₆)₂(H₂O)]}_n, the Ag^I cation is seven-coordinated and is surrounded by four oxo O atoms of the 2,3,5,6-tetra­oxo-4-nitro­pyridin-4-ide species [Ag—O = 2.3848 (19), 2.4931 (18), 2.5361 (18) and 2.573 (2) Å], two nitro O atoms [Ag—O = 2.644 (2) and 2.661 (2) Å], and one water mol­ecule [Ag—O = 2.3133 (19) Å]. The pyridin-4-ide mono-anions act as polydentate bridging ligands and form a three-dimensional network that is stabilized through O—H...O and N—H...O hydrogen bonds involving the coordinating water mol­ecule and the imide function as donator groups. The ammonium cations are located in the cavities of the framework and are also involved in hydrogen bonding to O atoms of the ligand.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.021
• wR factor = 0.066
• Data-to-parameter ratio = 9.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.78
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C2     -   C3     ...       1.53 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C5     -   C6     ...       1.55 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C8     -   C9     ...       1.54 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C11    -   C12    ...       1.54 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          6

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          8
PLAT004_ALERT_5_G Info: Polymeric Structure Found with Dimension .          2
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF          ? Do !
PLAT007_ALERT_5_G Note: Number of Unrefined Donor-H Atoms ........          2
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ          ? Check
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Ag1    --  O11     ..        5.8 su
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Ag1    --  O72     ..       12.0 su
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Ag1    --  O8_c    ..        8.3 su
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #         32
              O2   -O2   -C2      1.555   1.555   1.555              0.00 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #         33
              O2   -O2   -AG1     1.555   1.555   1.555              0.00 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #         35
              O3   -O3   -C3      1.555   1.555   1.555              0.00 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #         62
              O2   -C2   -O2      1.555   1.555   1.555              0.00 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #         68
              O3   -C3   -O3      1.555   1.555   1.555              0.00 Deg.
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          2
              H4 N
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         11
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          3
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......          ! Check

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  19 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 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
   7 ALERT type 4 Improvement, methodology, query or suggestion
   4 ALERT type 5 Informative message, check

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S1. Comment

1,2-dicarbonyl compounds attract great interest because of the features of their structure and high reactivity. One of the simplest representatives of them is oxalic acid. As described by S. Aldoshin (Aldoshin, 2008), bimetallic coordination polymers based on oxalate and thiooxalate bridging ligands possess different types of magnetic activity and can intercalate complex organic molecules and ions. These have been extensively used as building units in supramolecular coordination systems (Ohba & Okawa, 2000). The replacement of oxalate anions by other 1,2-dicarbonyl cyclic compounds may be of interest from the synthetic and practical point of view. As an example (Coronado et al. 2007), the paramagnetic and chiral anion [Fe(C₅O₅)₃]^3- has been combined with the organic donor BEDT-TTF DET (bis(ethylenedithio)tetrathiafulvalene) to synthesize a novel paramagnetic semiconductor with the first chirality-induced α-phase, α-(BEDT-TTF)5[Fe(C₅O₅)₃].5H₂O, and one of the few known paramagnetic molecular metals, β-(BEDT-TTF)5[Fe(C₅O₅)₃].C₆H₅CN. The variety of coordination modes, some geometric characteristics as well as electrical, magnetic and other properties of coordinate compounds of dibenzoquinone-1,4 derivatives of a general formula H₂C₆O₄X₂ are summarised by S. Kitagawa and S. Kawata (Kitagawa & Kawata, 2002). The present paper deals with the crystal structure determination of ammonium-silver 2,3,5,6-tetraoxo-4-nitropyridinate monohydrate (NH₄)[Ag(C₅HN₂O₆)₂(H₂O)]. The molecular structure of the above substance consists of Ag(I) and ammonium cations, two crystallographically unequivalent 2,3,5,6-tetraoxo-4-nitropyridinate mono anions, and one coordinated water molecule. Each of the Ag(I) cation displays sevenfold coordination by O2, O5, O8, and O11 of the keto-groups of the organic species. The Ag—O distances are 2.3848 (19); 2.4931 (18); 2.5361 (18); and 2.573 (2) Å. Two coordinate bonds involve the O atoms of the nitro-group of the organic anion (2.644 (2) and 2.661 (2) Å). The shortest distance in the coordination sphere of Ag(I) involves the coordinated water molecule (2.3133 (19) Å). The 2,3,5,6-tetraoxo-4-nitropyridinate anions act as polydentate bridging ligands. This coordination mode leads to formation of polymer chains. The coordination does not change significantly the C—O distances of the ligand comparing with its ammonium and sodium salts (Palkina et al., 2000; Kuzmina et al., 2004). The corresponding bond lengths are in the range 1.224 (3) to 1.220 (3) Å for the nitro-diketone fragment, and 1.210 (4) to 1.215 (4) Å for the amide fragment. These two fragments of the organic mono anion are connected by an almost single C—C bonds (C2—C3 length is 1.531 (4), and C5—C6 length is 1.544 (4) Å). The ammonium cation has the outer sphere character, and forms bridging H-bonds with the O atoms of the organic anions linking the polymer chains into three-dimensional structure. The H atoms of the coordinated water molecules are also involved into the H-bonding.

Related literature

For reviews of 1,2-dicarbonyl compounds, see: Aldoshin (2008); Ohba & Okawa (2000). The synthesis and crystal structures of ammonium and sodium 2,3,5,6-tetraoxo-4-nitropyridinates have been reported previously (Palkina et al., 2000; Kuzmina et al., 2004). The structure of the organic anion in its hexaaqua metal salts is described by Kovalchukova et al. (2003 and 2013). For references to related structures of metal complexes with cyclic polyoxdo-compounds, see: Coronado et al. (2007); Kitagawa & Kawata (2002).

S2. Experimental

Single crystals of C₁₀H₈AgN₅O₁₃ were grown by the slow evaporation of the ethanol solution of the 1-to-1 molar mixture of silver nitrate and ammonium 2,3,5,6-tetraoxo-4-nitropyridinate.

S3. Refinement

The structure of of (NH₄)[Ag(C₅HN₂O₆)₂(H₂O)] was solved by direct method and all non-hydrogen atoms were located and refined in anisotropically. All the hydrogen atoms were located in difference electron density syntheses and their positions refined subject to chemically reasonable restraints.

Computing details

Data collection: CAD-4-PC (Enraf–Nonius, 1993); cell refinement: CAD-4-PC (Enraf–Nonius, 1993); data reduction: CAD-4-PC (Enraf–Nonius, 1993); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: CIFTAB97 and SHELXL97 (Sheldrick, 2008).

Figures

	Fig. 1. ORTEP view of (NH4)[Ag(C5HN2O6)2(H2O)] with atom labeling scheme (displacement ellipsoids are drawn at the 50% probability level for non-hydrogen atoms).
	Fig. 2. Structure of the coordination sphere of Ag(I).
	Fig. 3. Molecular packing in the crystal of the complex along the crystallographic axis c.

catena-Poly[ammonium [aquabis(µ-2,3,5,6-tetraoxo-4-nitropyridin-4-ido)argentate(I)]]

Crystal data

(NH4)[Ag(C5HN2O6)2(H2O)]	F(000) = 1016
Mr = 514.08	Dx = 2.279 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 8.784 (2) Å	θ = 9.3–11.8°
b = 18.551 (4) Å	µ = 1.44 mm^−1
c = 9.195 (2) Å	T = 293 K
β = 90.70 (3)°	Plate, dark yellow
V = 1498.2 (5) Å^3	0.35 × 0.31 × 0.08 mm
Z = 4

Data collection

Enraf Nonius CAD-4 diffractometer	2094 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.014
β-filter monochromator	θmax = 25.5°, θmin = 2.2°
ω/2θ scans	h = 0→10
Absorption correction: part of the refinement model (ΔF) Walker & Stuart (1983)	k = 0→22
Tmin = 0.406, Tmax = 0.798	l = −11→11
2952 measured reflections	3 standard reflections every 60 min
2768 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.021	Hydrogen site location: difference Fourier map
wR(F^2) = 0.066	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0451P)^2 + 0.0506P] where P = (Fo^2 + 2Fc^2)/3
2768 reflections	(Δ/σ)max = 0.001
283 parameters	Δρmax = 0.42 e Å^−3
11 restraints	Δρmin = −0.58 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Ag1	0.68914 (2)	0.518350 (10)	0.16959 (2)	0.03092 (9)
O1	0.6981 (2)	0.43383 (10)	−0.0151 (2)	0.0367 (4)
O2	0.49428 (18)	0.55092 (10)	0.3355 (2)	0.0337 (4)
O3	0.2721 (2)	0.64390 (10)	0.3252 (3)	0.0437 (5)
O5	−0.0852 (2)	0.46912 (11)	0.3204 (2)	0.0430 (5)
O6	0.1206 (2)	0.36677 (10)	0.3468 (2)	0.0380 (4)
O71	0.4081 (2)	0.33294 (10)	0.3308 (2)	0.0374 (4)
O72	0.5781 (2)	0.41601 (11)	0.3380 (3)	0.0434 (5)
O8	0.59699 (19)	0.87943 (10)	0.5161 (2)	0.0346 (4)
O9	0.40503 (19)	0.77524 (10)	0.4454 (2)	0.0371 (4)
O11	0.7861 (2)	0.62851 (10)	0.3053 (2)	0.0335 (4)
O12	0.99467 (19)	0.72206 (10)	0.3830 (2)	0.0361 (4)
O131	1.0495 (2)	0.83839 (10)	0.5427 (3)	0.0440 (5)
O132	0.8913 (2)	0.92310 (9)	0.4915 (2)	0.0337 (4)
N2	1.1853 (2)	0.79954 (14)	0.1619 (3)	0.0356 (5)
N4	0.0902 (2)	0.55773 (12)	0.3224 (2)	0.0277 (4)
H4	0.0200	0.5900	0.3174	0.033*
N7	0.4426 (2)	0.39746 (11)	0.3354 (2)	0.0255 (4)
N10	0.5921 (2)	0.70207 (10)	0.3659 (2)	0.0234 (4)
H10	0.5263	0.6718	0.3324	0.028*
N13	0.9224 (2)	0.85893 (11)	0.5015 (2)	0.0250 (4)
C1	0.3262 (2)	0.45034 (14)	0.3364 (2)	0.0232 (5)
C2	0.3668 (3)	0.52426 (12)	0.3337 (2)	0.0230 (4)
C3	0.2389 (3)	0.58051 (13)	0.3276 (3)	0.0267 (5)
C5	0.0468 (3)	0.48715 (13)	0.3246 (3)	0.0264 (5)
C6	0.1700 (3)	0.42790 (13)	0.3368 (2)	0.0243 (5)
C7	0.8114 (2)	0.80583 (12)	0.4653 (2)	0.0219 (4)
C8	0.6544 (2)	0.82305 (12)	0.4741 (2)	0.0212 (4)
C9	0.5389 (3)	0.76440 (13)	0.4277 (2)	0.0236 (5)
C11	0.7427 (3)	0.68490 (12)	0.3543 (2)	0.0222 (4)
C12	0.8630 (3)	0.74009 (12)	0.4048 (2)	0.0222 (4)
H11	0.768 (3)	0.4067 (17)	−0.019 (5)	0.074 (6)*
H12	0.624 (3)	0.4089 (17)	−0.015 (5)	0.074 (6)*
H21	1.109 (3)	0.8260 (14)	0.166 (4)	0.074 (6)*
H22	1.263 (3)	0.8246 (14)	0.176 (4)	0.074 (6)*
H23	1.182 (4)	0.7675 (14)	0.225 (3)	0.074 (6)*
H24	1.190 (4)	0.7813 (16)	0.080 (2)	0.074 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ag1	0.03248 (13)	0.03008 (13)	0.03023 (13)	−0.00021 (7)	0.00124 (8)	−0.00114 (8)
O1	0.0281 (9)	0.0371 (10)	0.0449 (11)	−0.0023 (8)	0.0016 (8)	−0.0077 (8)
O2	0.0202 (8)	0.0337 (9)	0.0471 (11)	−0.0027 (7)	0.0010 (7)	−0.0058 (8)
O3	0.0299 (9)	0.0264 (9)	0.0747 (15)	0.0000 (8)	−0.0052 (9)	−0.0102 (9)
O5	0.0197 (9)	0.0485 (11)	0.0607 (13)	−0.0068 (8)	−0.0051 (8)	0.0142 (10)
O6	0.0330 (9)	0.0325 (10)	0.0485 (11)	−0.0067 (7)	−0.0014 (8)	0.0053 (8)
O71	0.0462 (11)	0.0284 (9)	0.0374 (10)	0.0044 (8)	−0.0032 (8)	0.0019 (8)
O72	0.0233 (9)	0.0408 (10)	0.0662 (14)	0.0076 (8)	0.0017 (9)	0.0079 (10)
O8	0.0241 (8)	0.0340 (9)	0.0455 (11)	0.0061 (7)	−0.0065 (8)	−0.0150 (8)
O9	0.0189 (9)	0.0374 (10)	0.0551 (12)	−0.0008 (7)	0.0040 (8)	−0.0096 (9)
O11	0.0280 (9)	0.0327 (10)	0.0398 (10)	0.0029 (7)	−0.0013 (7)	−0.0140 (8)
O12	0.0204 (9)	0.0394 (10)	0.0484 (11)	0.0035 (7)	0.0034 (8)	−0.0105 (8)
O131	0.0251 (9)	0.0359 (10)	0.0707 (14)	−0.0020 (8)	−0.0166 (9)	−0.0045 (9)
O132	0.0338 (9)	0.0223 (9)	0.0451 (11)	−0.0026 (7)	0.0010 (8)	−0.0044 (7)
N2	0.0285 (11)	0.0406 (13)	0.0376 (13)	−0.0039 (9)	−0.0015 (9)	−0.0011 (10)
N4	0.0200 (9)	0.0316 (10)	0.0313 (11)	0.0040 (8)	−0.0017 (8)	0.0003 (9)
N7	0.0291 (10)	0.0305 (11)	0.0168 (9)	0.0042 (8)	−0.0014 (7)	0.0022 (8)
N10	0.0193 (9)	0.0257 (10)	0.0253 (10)	−0.0024 (7)	−0.0025 (7)	−0.0033 (8)
N13	0.0232 (9)	0.0284 (10)	0.0234 (10)	−0.0014 (8)	−0.0005 (7)	−0.0030 (8)
C1	0.0214 (11)	0.0304 (12)	0.0178 (11)	0.0023 (9)	−0.0015 (8)	−0.0002 (9)
C2	0.0195 (10)	0.0311 (12)	0.0183 (10)	−0.0002 (9)	0.0004 (8)	−0.0034 (9)
C3	0.0244 (11)	0.0291 (13)	0.0266 (12)	−0.0007 (10)	−0.0020 (9)	−0.0059 (9)
C5	0.0234 (11)	0.0356 (13)	0.0202 (11)	−0.0018 (10)	−0.0018 (8)	0.0029 (10)
C6	0.0245 (11)	0.0300 (12)	0.0184 (11)	−0.0022 (9)	−0.0013 (9)	0.0011 (9)
C7	0.0211 (11)	0.0239 (10)	0.0204 (11)	−0.0023 (9)	−0.0028 (8)	0.0001 (9)
C8	0.0197 (10)	0.0250 (11)	0.0187 (10)	0.0006 (8)	−0.0022 (8)	−0.0022 (9)
C9	0.0221 (11)	0.0269 (11)	0.0218 (11)	−0.0003 (9)	−0.0013 (9)	−0.0024 (9)
C11	0.0250 (11)	0.0257 (11)	0.0157 (10)	0.0020 (9)	−0.0015 (8)	−0.0002 (9)
C12	0.0202 (11)	0.0257 (11)	0.0207 (10)	0.0020 (9)	0.0001 (8)	0.0005 (9)

Geometric parameters (Å, º)

Ag1—O1	2.3133 (19)	O132—N13	1.225 (3)
Ag1—O2	2.3848 (19)	O132—Ag1^iv	2.661 (2)
Ag1—O8^i	2.4931 (18)	N2—H21	0.832 (19)
Ag1—O11	2.5361 (18)	N2—H22	0.83 (2)
Ag1—O5^ii	2.573 (2)	N2—H23	0.830 (19)
Ag1—O72	2.644 (2)	N2—H24	0.827 (19)
Ag1—O132^i	2.661 (2)	N4—C5	1.364 (3)
O1—H11	0.80 (3)	N4—C3	1.373 (3)
O1—H12	0.80 (3)	N4—H4	0.8600
O2—C2	1.224 (3)	N7—C1	1.417 (3)
O3—C3	1.212 (3)	N10—C11	1.366 (3)
O5—C5	1.206 (3)	N10—C9	1.373 (3)
O5—Ag1^iii	2.573 (2)	N10—H10	0.8600
O6—C6	1.218 (3)	N13—C7	1.423 (3)
O71—N7	1.235 (3)	C1—C2	1.417 (3)
O72—N7	1.239 (3)	C1—C6	1.434 (3)
O8—C8	1.225 (3)	C2—C3	1.534 (3)
O8—Ag1^iv	2.4931 (18)	C5—C6	1.546 (3)
O9—C9	1.206 (3)	C7—C12	1.417 (3)
O11—C11	1.203 (3)	C7—C8	1.419 (3)
O12—C12	1.223 (3)	C8—C9	1.544 (3)
O131—N13	1.235 (3)	C11—C12	1.539 (3)
O1—Ag1—O2	132.26 (6)	C5—N4—H4	117.9
O1—Ag1—O2	132.26 (6)	C3—N4—H4	117.9
O2—Ag1—O2	0.00 (5)	O71—N7—O72	120.3 (2)
O1—Ag1—O8^i	96.52 (7)	O71—N7—C1	119.6 (2)
O2—Ag1—O8^i	86.50 (7)	O72—N7—C1	120.0 (2)
O2—Ag1—O8^i	86.50 (7)	C11—N10—C9	124.3 (2)
O1—Ag1—O11	153.27 (7)	C11—N10—H10	117.8
O2—Ag1—O11	73.76 (6)	C9—N10—H10	117.8
O2—Ag1—O11	73.76 (6)	O132—N13—O131	121.6 (2)
O8^i—Ag1—O11	76.73 (7)	O132—N13—C7	120.24 (19)
O1—Ag1—O5^ii	97.02 (7)	O131—N13—C7	118.21 (19)
O2—Ag1—O5^ii	107.42 (7)	N7—C1—C2	119.23 (19)
O2—Ag1—O5^ii	107.42 (7)	N7—C1—C6	119.3 (2)
O8^i—Ag1—O5^ii	144.87 (6)	C2—C1—C6	121.5 (2)
O11—Ag1—O5^ii	76.64 (7)	O2—C2—O2	0.00 (16)
O1—Ag1—O72	87.67 (7)	O2—C2—C1	128.4 (2)
O2—Ag1—O72	62.25 (7)	O2—C2—C1	128.4 (2)
O2—Ag1—O72	62.25 (7)	O2—C2—C3	113.3 (2)
O8^i—Ag1—O72	139.31 (6)	O2—C2—C3	113.3 (2)
O11—Ag1—O72	114.48 (7)	C1—C2—C3	118.3 (2)
O5^ii—Ag1—O72	73.55 (6)	O3—C3—O3	0.0 (2)
O1—Ag1—O132^i	78.24 (6)	O3—C3—N4	121.8 (2)
O2—Ag1—O132^i	141.23 (6)	O3—C3—N4	121.8 (2)
O2—Ag1—O132^i	141.23 (6)	O3—C3—C2	119.0 (2)
O8^i—Ag1—O132^i	63.63 (6)	O3—C3—C2	119.0 (2)
O11—Ag1—O132^i	75.60 (6)	N4—C3—C2	119.2 (2)
O5^ii—Ag1—O132^i	87.76 (6)	O5—C5—N4	122.3 (2)
O72—Ag1—O132^i	155.09 (5)	O5—C5—C6	118.5 (2)
Ag1—O1—H11	120 (3)	N4—C5—C6	119.2 (2)
Ag1—O1—H12	111 (3)	O6—C6—C1	127.8 (2)
H11—O1—H12	105.3 (9)	O6—C6—C5	114.7 (2)
O2—O2—C2	0 (10)	C1—C6—C5	117.6 (2)
O2—O2—Ag1	0 (6)	C12—C7—C8	122.1 (2)
C2—O2—Ag1	123.54 (16)	C12—C7—N13	117.8 (2)
O3—O3—C3	0 (10)	C8—C7—N13	119.65 (19)
C5—O5—Ag1^iii	130.73 (17)	O8—C8—C7	127.9 (2)
N7—O72—Ag1	123.30 (16)	O8—C8—C9	114.66 (19)
C8—O8—Ag1^iv	134.07 (15)	C7—C8—C9	117.45 (19)
C11—O11—Ag1	141.17 (16)	O9—C9—N10	122.3 (2)
N13—O132—Ag1^iv	120.06 (15)	O9—C9—C8	118.9 (2)
H21—N2—H22	108.8 (9)	N10—C9—C8	118.83 (19)
H21—N2—H23	111 (3)	O11—C11—N10	122.9 (2)
H22—N2—H23	109.0 (9)	O11—C11—C12	118.2 (2)
H21—N2—H24	109.7 (9)	N10—C11—C12	118.9 (2)
H22—N2—H24	108 (3)	O12—C12—C7	127.4 (2)
H23—N2—H24	110.0 (9)	O12—C12—C11	114.6 (2)
C5—N4—C3	124.1 (2)	C7—C12—C11	118.00 (19)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O11^iii	0.86	2.18	2.979 (3)	155
N10—H10···O2	0.86	2.26	2.945 (3)	137
N10—H10···O3	0.86	2.29	3.030 (3)	144
O1—H11···O131^v	0.80 (3)	2.06 (3)	2.851 (3)	177 (5)
O1—H12···O8^vi	0.80 (3)	2.02 (3)	2.781 (2)	160 (3)
N2—H21···O6^vii	0.83 (2)	2.16 (2)	2.962 (3)	163 (3)
N2—H22···O72^viii	0.83 (2)	2.20 (2)	2.998 (3)	160 (3)

Symmetry codes: (iii) x−1, y, z; (v) −x+2, y−1/2, −z+1/2; (vi) −x+1, y−1/2, −z+1/2; (vii) −x+1, y+1/2, −z+1/2; (viii) −x+2, y+1/2, −z+1/2.