Bis(1,10-phenanthroline-5,6-dione-κ2N,N′)silver(I) 2-hy­droxy-3,5-dinitro­benzoate

Wang, S.-T.; Che, G.-B.; Liu, C.-B.; Wang, X.; Liu, L.

doi:10.1107/S1600536811053785

Bis(1,10-phenanthroline-5,6-dione-κ²N,N′)silver(I) 2-hydroxy-3,5-dinitrobenzoate

S.-T. Wang, G.-B. Che, C.-B. Liu, X. Wang and L. Liu

In the cation of the title salt, [Ag(C₁₂H₆N₂O₂)₂](C₇H₃N₂O₇), the Ag^I atom is coordinated in a distorted tetrahedral geometry by four N atoms from two 1,10-phenanthroline-5,6-dione ligands, while the 3,5-dinitrosalicylate anion has only a short contact [2.847 (6) Å] between one of its O atoms and the Ag^I atom. The dihedral angle between the two 1,10-phenanthroline-5,6-dione ligands is 58.4 (1)°. There is an intramolecular O—H

O hydrogen bond in the 3,5-dinitrosalicylate anion.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811053785/vn2025sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536811053785/vn2025Isup2.hkl Contains datablock I

CCDC reference: 861712

checkCIF report

Key indicators

Single-crystal X-ray study
T = 174 K
Mean (C-C) = 0.011 Å
R factor = 0.083
wR factor = 0.163
Data-to-parameter ratio = 11.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........         O1
PLAT342_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0110 Ang
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          9
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         30
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         11
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          2

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         14
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained Atom Sites ....          8
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large.      13.47
PLAT432_ALERT_2_G Short Inter X...Y Contact  O1     ..  C18     ..       2.94 Ang.
PLAT432_ALERT_2_G Short Inter X...Y Contact  O1     ..  C17     ..       3.01 Ang.
PLAT432_ALERT_2_G Short Inter X...Y Contact  O9     ..  C17     ..       2.74 Ang.
PLAT432_ALERT_2_G Short Inter X...Y Contact  O9     ..  C18     ..       2.89 Ang.
PLAT432_ALERT_2_G Short Inter X...Y Contact  O9     ..  C16     ..       2.92 Ang.
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         22

   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
  10 ALERT level G = General information/check it is not something unexpected

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

Comment top

The design and construction of supramolecular architectures have received considerable attention in recent years, mostly motivated by their intriguing structural features and potential applications in molecular adsorption, molecular sensing, magnetism, catalysis and non-linear optics (Che et al., 2008). Metal complexes with 1,10-phenantroline-5,6-dione (L) and 3,5-dinitrosalicylic acid as important ligands for the construction of metal-organic supramolecular architectures have been increasingly studied over recent years (Hiort et al., 1993; Onuegbu et al., 2009; Song et al., 2007). We report herein on the crystal structure of the title compound (Fig. 1). The molecular structure of the title compound, is made up of one [AgL₂]⁺ cation and one 3,5-dinitrosalicylate anion. The Ag^I atom is surrounded by four N atoms from two 1,10-phenanthroline-5,6-dione ligands, while the 3,5-dinitrosalicylate ligand is uncoordinated. In the compound the dihedral angle between the phendione ligand A (C1-C12, N1, N2, O1 and O2) and B (C13-C24, N3, N4, O3, and O4) is 58.4 (1)°. The dihedral angle between B and 3,5-dinitrosalicylate ligand C (C25-C31, N5, N6, O5-O11) is 56.1 (2)°. The dihedral angle between A and C is 2.4 (9)°, suggesting that the planes of rings A and C are almost parallel. In addition, in the 3,5-dinitrosalicylate ligand, there is one intramolecular O–H···O hydrogen bond (Fig. 2).

Related literature top

For a general background to the structures and potential applications of supramolecular architectures with 1,10-phenantroline-5,6-dione and 3,5-dinitrosalicylic acid, see: Hiort et al. (1993); Song et al. (2007); Che et al. (2008); Onuegbu et al. (2009). For the synthesis of the 1,10-phenantroline-5,6-dione ligand, see: Dickeson & Sumers (1970).

Experimental top

The L ligand was synthesized according to the literature method (Dickeson & Sumers, 1970). The title compound was synthesized under hydrothermal conditions. A mixture of L (0.042 g, 0.2 mmol), 3,5-dinitrosalicylic acid (0.046 g, 0.2 mmol), AgNO₃ (0.034 g, 0.2 mmol) and water (10 mL) was placed in a 25 mL Teflon-lined autoclave and heated for 3 days at 433 K under autogenous pressure. Upon cooling and opening the bomb, yellow block-shaped crystals were obtained, then washed with water and dried in air.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS-97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL-97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. All H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. A view of the crystal packing of the title compound, showing the O–H···O hydrogen bonds interaction.

(I) top

Crystal data top

C₂₄H₁₂AgN₄O₄·C₇H₃N₂O₇	F(000) = 1512
M_r = 755.36	D_x = 1.817 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5197 reflections
a = 11.757 (2) Å	θ = 3.2–25.4°
b = 18.297 (4) Å	µ = 0.81 mm⁻¹
c = 13.223 (3) Å	T = 174 K
β = 103.91 (3)°	Prism, yellow
V = 2761.1 (11) Å³	0.3 × 0.24 × 0.2 mm
Z = 4

Data collection top

Oxford Diffraction Gemini R Ultra diffractometer	5059 independent reflections
Radiation source: fine-focus sealed tube	3914 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
ω scans	θ_max = 25.4°, θ_min = 3.2°
Absorption correction: multi-scan SADABS (Bruker, 2002)	h = −14→11
T_min = 0.780, T_max = 0.910	k = −17→22
12726 measured reflections	l = −15→13

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)] = 0.083	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.163	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0354P)² + 13.4705P] where P = (F_o² + 2F_c²)/3
5013 reflections	(Δ/σ)_max < 0.001
442 parameters	Δρ_max = 1.11 e Å⁻³
22 restraints	Δρ_min = −0.72 e Å⁻³

Crystal data top

C₂₄H₁₂AgN₄O₄·C₇H₃N₂O₇	V = 2761.1 (11) Å³
M_r = 755.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.757 (2) Å	µ = 0.81 mm⁻¹
b = 18.297 (4) Å	T = 174 K
c = 13.223 (3) Å	0.3 × 0.24 × 0.2 mm
β = 103.91 (3)°

Data collection top

Oxford Diffraction Gemini R Ultra diffractometer	5059 independent reflections
Absorption correction: multi-scan SADABS (Bruker, 2002)	3914 reflections with I > 2σ(I)
T_min = 0.780, T_max = 0.910	R_int = 0.052
12726 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.083	22 restraints
wR(F²) = 0.163	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0354P)² + 13.4705P] where P = (F_o² + 2F_c²)/3
5013 reflections	Δρ_max = 1.11 e Å⁻³
442 parameters	Δρ_min = −0.72 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.21081 (6)	0.44038 (3)	0.52487 (5)	0.0540 (2)
C1	0.4793 (7)	0.5137 (4)	0.6222 (5)	0.0435 (18)
H1	0.4399	0.5580	0.6074	0.052*
C2	0.5976 (7)	0.5157 (4)	0.6690 (6)	0.048 (2)
H2	0.6371	0.5599	0.6845	0.058*
C3	0.6552 (7)	0.4497 (4)	0.6920 (6)	0.0470 (19)
H3	0.7345	0.4488	0.7248	0.056*
C4	0.5941 (6)	0.3844 (4)	0.6659 (5)	0.0380 (16)
C5	0.6515 (9)	0.3155 (4)	0.6883 (7)	0.062 (2)
C6	0.5895 (7)	0.2505 (5)	0.6710 (7)	0.063 (2)
C7	0.4678 (6)	0.2544 (4)	0.6244 (5)	0.0431 (18)
C8	0.3994 (8)	0.1885 (4)	0.6037 (6)	0.053 (2)
H8	0.4340	0.1433	0.6229	0.064*
C9	0.2836 (9)	0.1930 (5)	0.5557 (7)	0.063 (2)
H9	0.2388	0.1508	0.5403	0.075*
C10	0.2342 (7)	0.2594 (5)	0.5305 (7)	0.055 (2)
H10	0.1552	0.2613	0.4966	0.066*
C11	0.4090 (6)	0.3201 (3)	0.5978 (5)	0.0338 (16)
C12	0.4738 (5)	0.3869 (3)	0.6196 (5)	0.0335 (16)
C13	0.0848 (7)	0.4147 (4)	0.2775 (7)	0.055 (2)
H13	0.1080	0.3666	0.2933	0.066*
C14	0.0374 (8)	0.4324 (5)	0.1743 (7)	0.061 (2)
H14	0.0287	0.3972	0.1223	0.073*
C15	0.0034 (7)	0.5036 (5)	0.1506 (6)	0.053 (2)
H15	−0.0298	0.5170	0.0820	0.064*
C16	0.0190 (6)	0.5564 (4)	0.2312 (5)	0.0432 (18)
C17	−0.0122 (5)	0.6312 (4)	0.2098 (5)	0.052 (2)
C18	−0.0077 (7)	0.6805 (4)	0.2948 (6)	0.055 (2)
C19	0.0460 (6)	0.6571 (4)	0.3993 (6)	0.0447 (18)
C20	0.0688 (7)	0.7058 (4)	0.4853 (7)	0.055 (2)
H20	0.0483	0.7548	0.4749	0.067*
C21	0.1205 (8)	0.6816 (5)	0.5829 (7)	0.059 (2)
H21	0.1348	0.7131	0.6398	0.071*
C22	0.1506 (7)	0.6090 (5)	0.5945 (6)	0.056 (2)
H22	0.1865	0.5925	0.6611	0.067*
C23	0.0809 (6)	0.5844 (3)	0.4175 (5)	0.0369 (16)
C24	0.0632 (5)	0.5330 (3)	0.3334 (5)	0.0322 (15)
C25	0.6149 (7)	0.4146 (4)	0.9278 (5)	0.0419 (18)
C26	0.5083 (7)	0.4530 (4)	0.8867 (5)	0.0411 (18)
C27	0.4075 (6)	0.4103 (4)	0.8430 (5)	0.0388 (17)
C28	0.4092 (7)	0.3351 (4)	0.8460 (5)	0.0433 (18)
H28	0.3421	0.3080	0.8181	0.052*
C29	0.5165 (8)	0.3002 (4)	0.8928 (5)	0.0434 (19)
C30	0.6177 (7)	0.3387 (4)	0.9327 (6)	0.0435 (18)
H30	0.6871	0.3143	0.9625	0.052*
C31	0.2956 (8)	0.4467 (5)	0.7881 (6)	0.050 (2)
N1	0.4178 (5)	0.4524 (3)	0.5970 (4)	0.0347 (13)
N2	0.2931 (5)	0.3228 (3)	0.5518 (5)	0.0399 (14)
N3	0.0992 (5)	0.4629 (3)	0.3562 (5)	0.0422 (15)
N4	0.1319 (5)	0.5605 (3)	0.5164 (5)	0.0423 (14)
N5	0.7268 (7)	0.4516 (5)	0.9629 (5)	0.0587 (19)
N6	0.5177 (8)	0.2213 (4)	0.9005 (5)	0.0560 (19)
O1	0.7645 (7)	0.3121 (4)	0.7270 (6)	0.088 (2)
O2	0.6419 (7)	0.1890 (4)	0.6988 (6)	0.096 (2)
O3	−0.0430 (5)	0.6542 (3)	0.1162 (4)	0.0700 (18)
O4	−0.0502 (6)	0.7445 (3)	0.2780 (5)	0.080 (2)
O5	0.8165 (6)	0.4147 (4)	0.9745 (6)	0.091 (2)
O6	0.7295 (6)	0.5175 (4)	0.9763 (6)	0.085 (2)
O7	0.5032 (6)	0.5236 (3)	0.8852 (4)	0.0608 (16)
H7	0.4365	0.5366	0.8565	0.091*
O8	0.2947 (6)	0.5172 (3)	0.7949 (5)	0.0684 (17)
O9	0.2133 (5)	0.4109 (4)	0.7368 (5)	0.0641 (16)
O10	0.4296 (7)	0.1876 (3)	0.8584 (5)	0.0713 (19)
O11	0.6097 (6)	0.1916 (3)	0.9511 (5)	0.0684 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0472 (4)	0.0491 (4)	0.0609 (4)	0.0150 (3)	0.0036 (3)	0.0149 (3)
C1	0.056 (5)	0.038 (4)	0.039 (4)	−0.007 (4)	0.015 (4)	0.001 (3)
C2	0.054 (5)	0.046 (5)	0.048 (5)	−0.011 (4)	0.019 (4)	−0.001 (4)
C3	0.033 (4)	0.065 (6)	0.042 (4)	−0.003 (4)	0.008 (3)	−0.006 (4)
C4	0.036 (4)	0.043 (4)	0.037 (4)	0.007 (3)	0.013 (3)	0.001 (3)
C5	0.084 (7)	0.059 (5)	0.049 (5)	0.022 (5)	0.028 (5)	0.008 (4)
C6	0.067 (5)	0.068 (6)	0.057 (5)	0.007 (5)	0.019 (4)	−0.001 (5)
C7	0.056 (4)	0.045 (4)	0.033 (4)	0.005 (4)	0.020 (3)	0.001 (3)
C8	0.085 (5)	0.031 (4)	0.049 (5)	0.014 (4)	0.026 (4)	0.008 (4)
C9	0.077 (5)	0.053 (5)	0.064 (6)	−0.012 (5)	0.027 (4)	−0.010 (5)
C10	0.043 (5)	0.050 (5)	0.072 (6)	−0.002 (4)	0.014 (4)	−0.009 (4)
C11	0.044 (4)	0.027 (4)	0.031 (4)	0.008 (3)	0.011 (3)	0.001 (3)
C12	0.041 (4)	0.031 (4)	0.030 (4)	−0.001 (3)	0.011 (3)	0.002 (3)
C13	0.051 (5)	0.036 (4)	0.072 (6)	−0.001 (4)	0.005 (4)	−0.002 (4)
C14	0.056 (6)	0.057 (6)	0.063 (6)	−0.002 (4)	0.002 (4)	−0.024 (5)
C15	0.047 (5)	0.060 (6)	0.047 (5)	−0.001 (4)	0.003 (4)	−0.002 (4)
C16	0.032 (4)	0.042 (4)	0.053 (5)	0.000 (3)	0.006 (3)	0.004 (4)
C17	0.041 (5)	0.053 (5)	0.058 (5)	0.003 (4)	0.002 (4)	0.019 (4)
C18	0.041 (5)	0.049 (5)	0.071 (6)	−0.004 (4)	0.004 (4)	0.006 (5)
C19	0.038 (4)	0.037 (4)	0.058 (5)	0.001 (3)	0.008 (4)	0.001 (4)
C20	0.045 (5)	0.035 (4)	0.084 (7)	0.001 (4)	0.012 (5)	−0.008 (4)
C21	0.052 (5)	0.055 (5)	0.069 (6)	0.003 (4)	0.012 (5)	−0.017 (5)
C22	0.047 (5)	0.070 (6)	0.047 (5)	−0.002 (4)	0.004 (4)	−0.005 (4)
C23	0.028 (4)	0.036 (4)	0.045 (4)	0.003 (3)	0.005 (3)	0.002 (3)
C24	0.022 (3)	0.029 (4)	0.045 (4)	0.000 (3)	0.006 (3)	0.004 (3)
C25	0.056 (5)	0.040 (4)	0.029 (4)	−0.010 (4)	0.008 (3)	−0.003 (3)
C26	0.061 (5)	0.033 (4)	0.033 (4)	0.001 (4)	0.018 (4)	−0.003 (3)
C27	0.045 (5)	0.039 (4)	0.035 (4)	0.001 (3)	0.016 (3)	0.003 (3)
C28	0.061 (5)	0.042 (4)	0.032 (4)	−0.008 (4)	0.019 (4)	−0.002 (3)
C29	0.071 (6)	0.030 (4)	0.035 (4)	0.006 (4)	0.024 (4)	0.006 (3)
C30	0.047 (5)	0.046 (5)	0.038 (4)	0.004 (4)	0.013 (3)	0.004 (3)
C31	0.060 (6)	0.049 (5)	0.048 (5)	0.014 (4)	0.024 (4)	0.011 (4)
N1	0.036 (3)	0.032 (3)	0.035 (3)	0.002 (3)	0.008 (3)	0.000 (3)
N2	0.038 (4)	0.037 (3)	0.045 (3)	0.000 (3)	0.009 (3)	−0.001 (3)
N3	0.038 (4)	0.032 (3)	0.053 (4)	0.000 (3)	0.004 (3)	−0.002 (3)
N4	0.037 (3)	0.043 (4)	0.046 (4)	0.003 (3)	0.007 (3)	0.006 (3)
N5	0.059 (5)	0.071 (6)	0.042 (4)	−0.011 (4)	0.006 (3)	−0.007 (4)
N6	0.091 (6)	0.039 (4)	0.046 (4)	0.003 (4)	0.032 (4)	0.003 (3)
O1	0.081 (5)	0.099 (6)	0.084 (5)	0.033 (4)	0.020 (4)	0.021 (4)
O2	0.086 (6)	0.079 (5)	0.110 (6)	0.022 (4)	−0.003 (4)	0.000 (4)
O3	0.067 (4)	0.071 (4)	0.067 (4)	0.003 (3)	0.005 (3)	0.024 (3)
O4	0.097 (5)	0.040 (4)	0.094 (5)	0.018 (3)	0.005 (4)	0.016 (3)
O5	0.055 (5)	0.099 (6)	0.113 (6)	−0.004 (4)	0.008 (4)	−0.033 (5)
O6	0.089 (5)	0.050 (4)	0.098 (5)	−0.024 (4)	−0.016 (4)	0.002 (4)
O7	0.086 (5)	0.039 (3)	0.058 (4)	0.000 (3)	0.019 (3)	−0.001 (3)
O8	0.080 (5)	0.057 (4)	0.073 (4)	0.022 (3)	0.028 (3)	0.010 (3)
O9	0.041 (4)	0.081 (4)	0.069 (4)	0.004 (3)	0.012 (3)	−0.002 (3)
O10	0.110 (6)	0.039 (3)	0.066 (4)	−0.015 (4)	0.025 (4)	−0.003 (3)
O11	0.088 (5)	0.042 (3)	0.083 (4)	0.017 (3)	0.036 (4)	0.021 (3)

Geometric parameters (Å, º) top

Ag1—N1	2.400 (6)	C16—C24	1.394 (7)
Ag1—N2	2.351 (6)	C16—C17	1.428 (7)
Ag1—N3	2.337 (6)	C17—O3	1.275 (7)
Ag1—N4	2.377 (6)	C17—C18	1.432 (8)
Ag1—O9	2.847 (6)	C18—O4	1.272 (9)
C1—N1	1.333 (9)	C18—C19	1.438 (8)
C1—C2	1.380 (11)	C19—C23	1.397 (7)
C1—H1	0.9300	C19—C20	1.419 (11)
C2—C3	1.383 (11)	C20—C21	1.361 (12)
C2—H2	0.9300	C20—H20	0.9300
C3—C4	1.394 (10)	C21—C22	1.374 (12)
C3—H3	0.9300	C21—H21	0.9300
C4—C12	1.400 (7)	C22—N4	1.340 (10)
C4—C5	1.426 (8)	C22—H22	0.9300
C5—O1	1.304 (11)	C23—N4	1.373 (8)
C5—C6	1.385 (8)	C23—C24	1.433 (7)
C6—O2	1.293 (10)	C24—N3	1.362 (8)
C6—C7	1.417 (8)	C25—C30	1.390 (10)
C7—C11	1.390 (7)	C25—C26	1.426 (10)
C7—C8	1.438 (11)	C25—N5	1.454 (10)
C8—C9	1.358 (12)	C26—O7	1.292 (8)
C8—H8	0.9300	C26—C27	1.421 (10)
C9—C10	1.353 (12)	C27—C28	1.377 (10)
C9—H9	0.9300	C27—C31	1.498 (11)
C10—N2	1.347 (10)	C28—C29	1.416 (11)
C10—H10	0.9300	C28—H28	0.9300
C11—N2	1.353 (8)	C29—C30	1.374 (11)
C11—C12	1.432 (7)	C29—N6	1.448 (10)
C12—N1	1.365 (8)	C30—H30	0.9300
C13—N3	1.343 (10)	C31—O9	1.228 (10)
C13—C14	1.383 (12)	C31—O8	1.293 (10)
C13—H13	0.9300	N5—O6	1.218 (9)
C14—C15	1.376 (11)	N5—O5	1.230 (9)
C14—H14	0.9300	N6—O10	1.218 (9)
C15—C16	1.417 (10)	N6—O11	1.252 (9)
C15—H15	0.9300	O7—H7	0.8200

N3—Ag1—N2	115.0 (2)	O4—C18—C19	120.4 (7)
N3—Ag1—N4	70.7 (2)	C17—C18—C19	119.4 (7)
N2—Ag1—N4	174.1 (2)	C23—C19—C20	117.9 (7)
N3—Ag1—N1	130.3 (2)	C23—C19—C18	119.5 (7)
N2—Ag1—N1	71.5 (2)	C20—C19—C18	122.5 (7)
N4—Ag1—N1	106.3 (2)	C21—C20—C19	120.8 (7)
N3—Ag1—O9	147.53 (19)	C21—C20—H20	119.6
N2—Ag1—O9	76.74 (19)	C19—C20—H20	119.6
N4—Ag1—O9	97.64 (19)	C20—C21—C22	117.7 (8)
N1—Ag1—O9	81.75 (18)	C20—C21—H21	121.2
N1—C1—C2	124.2 (7)	C22—C21—H21	121.2
N1—C1—H1	117.9	N4—C22—C21	124.4 (8)
C2—C1—H1	117.9	N4—C22—H22	117.8
C1—C2—C3	117.6 (7)	C21—C22—H22	117.8
C1—C2—H2	121.2	N4—C23—C19	120.7 (6)
C3—C2—H2	121.2	N4—C23—C24	118.6 (6)
C2—C3—C4	119.9 (7)	C19—C23—C24	120.6 (6)
C2—C3—H3	120.0	N3—C24—C16	121.9 (6)
C4—C3—H3	120.0	N3—C24—C23	117.9 (6)
C3—C4—C12	119.1 (6)	C16—C24—C23	120.1 (6)
C3—C4—C5	121.0 (7)	C30—C25—C26	121.4 (7)
C12—C4—C5	119.9 (7)	C30—C25—N5	116.1 (7)
O1—C5—C6	118.0 (7)	C26—C25—N5	122.5 (7)
O1—C5—C4	120.7 (8)	O7—C26—C27	120.8 (7)
C6—C5—C4	121.3 (9)	O7—C26—C25	122.2 (7)
O2—C6—C5	120.3 (8)	C27—C26—C25	117.0 (6)
O2—C6—C7	122.0 (8)	C28—C27—C26	122.2 (7)
C5—C6—C7	117.8 (8)	C28—C27—C31	117.6 (7)
C11—C7—C6	122.8 (7)	C26—C27—C31	120.2 (7)
C11—C7—C8	117.1 (7)	C27—C28—C29	117.9 (7)
C6—C7—C8	120.1 (7)	C27—C28—H28	121.0
C9—C8—C7	119.4 (7)	C29—C28—H28	121.0
C9—C8—H8	120.3	C30—C29—C28	122.3 (7)
C7—C8—H8	120.3	C30—C29—N6	119.4 (8)
C10—C9—C8	119.5 (8)	C28—C29—N6	118.2 (8)
C10—C9—H9	120.3	C29—C30—C25	119.0 (7)
C8—C9—H9	120.3	C29—C30—H30	120.5
N2—C10—C9	123.6 (8)	C25—C30—H30	120.5
N2—C10—H10	118.2	O9—C31—O8	123.5 (8)
C9—C10—H10	118.2	O9—C31—C27	120.9 (8)
N2—C11—C7	122.1 (6)	O8—C31—C27	115.5 (8)
N2—C11—C12	119.3 (5)	C1—N1—C12	118.7 (6)
C7—C11—C12	118.6 (6)	C1—N1—Ag1	127.8 (5)
N1—C12—C4	120.6 (6)	C12—N1—Ag1	113.4 (4)
N1—C12—C11	119.9 (6)	C10—N2—C11	118.3 (6)
C4—C12—C11	119.5 (6)	C10—N2—Ag1	125.8 (5)
N3—C13—C14	123.8 (8)	C11—N2—Ag1	115.8 (4)
N3—C13—H13	118.1	C13—N3—C24	118.2 (6)
C14—C13—H13	118.1	C13—N3—Ag1	124.2 (5)
C15—C14—C13	118.2 (8)	C24—N3—Ag1	116.8 (4)
C15—C14—H14	120.9	C22—N4—C23	118.5 (6)
C13—C14—H14	120.9	C22—N4—Ag1	125.9 (5)
C14—C15—C16	119.8 (7)	C23—N4—Ag1	114.5 (4)
C14—C15—H15	120.1	O6—N5—O5	122.3 (8)
C16—C15—H15	120.1	O6—N5—C25	119.8 (8)
C24—C16—C15	118.0 (6)	O5—N5—C25	117.8 (8)
C24—C16—C17	120.3 (6)	O10—N6—O11	123.8 (7)
C15—C16—C17	121.7 (6)	O10—N6—C29	118.7 (8)
O3—C17—C18	120.3 (7)	O11—N6—C29	117.6 (8)
O3—C17—C16	120.4 (7)	C26—O7—H7	109.5
C18—C17—C16	119.3 (6)	C31—O9—Ag1	105.3 (5)
O4—C18—C17	120.2 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7···O8	0.82	1.71	2.457 (9)	151

Experimental details

Crystal data
Chemical formula	C₂₄H₁₂AgN₄O₄·C₇H₃N₂O₇
M_r	755.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	174
a, b, c (Å)	11.757 (2), 18.297 (4), 13.223 (3)
β (°)	103.91 (3)
V (Å³)	2761.1 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.81
Crystal size (mm)	0.3 × 0.24 × 0.2

Data collection
Diffractometer	Oxford Diffraction Gemini R Ultra diffractometer
Absorption correction	Multi-scan SADABS (Bruker, 2002)
T_min, T_max	0.780, 0.910
No. of measured, independent and observed [I > 2σ(I)] reflections	12726, 5059, 3914
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.083, 0.163, 1.11
No. of reflections	5013
No. of parameters	442
No. of restraints	22
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0354P)² + 13.4705P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.11, −0.72

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS-97 (Sheldrick, 2008), SHELXL-97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Ag1—N1	2.400 (6)	Ag1—N3	2.337 (6)
Ag1—N2	2.351 (6)	Ag1—N4	2.377 (6)