Bis[diamminesilver(I)] 5-nitro­iso­phthalate monohydrate

Sun, D.; Luo, G.-G.; Zhang, N.; Huang, R.-B.

doi:10.1107/S1600536810007725

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Pages m406-m407

doi:10.1107/S1600536810007725

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Bis[diamminesilver(I)] 5-nitroisophthalate monohydrate

Di Sun,^a Geng-Geng Luo,^a Na Zhang ^a and Rong-Bin Huang ^a ^*

^aDepartment of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, People's Republic of China
^*Correspondence e-mail: rbhuang@xmu.edu.cn

(Received 4 February 2010; accepted 1 March 2010; online 13 March 2010)

In the title compound, [Ag(NH₃)₂]₂(C₈H₃NO₆)·H₂O, the cations have an almost linear coordination geometry with two ammine ligands and interact with the water molecules [Ag⋯O_water = 2.725 (4) and 2.985 (4) Å]. In the crystal, N—H⋯O and O—H⋯O hydrogen bonds, combined with weak (lone pair)⋯π [O⋯centroid distance = 3.401 (4) Å] and π–π stacking [centroid–centroid distance = 3.975 (3) Å] interactions, stabilize the three-dimensional supramolecular network.

Related literature

For general background to crystal engineering and supramolecular chemistry, see: Batten & Robson (1998 ); Blake et al. (1999 ); Yaghi et al. (2003 ). For general background to non-covalent interactions, see: Biswas et al. (2009 ); Egli & Arkhel (2007 ); Jeffrey et al. (1985 ); Mooibroek et al. (2006 ); Nishio et al. (1998 ); Rahman et al. (2003 ). For related structures, see: Sun, Luo, Huang et al. (2009 ); Sun, Luo, Xu et al. (2009 ); Sun, Luo, Zhang et al. (2009 ); You & Zhu (2004 ); You et al. (2004 ); Zheng et al. (2002 , 2007 ).

Experimental

Crystal data

[Ag(NH₃)₂]₂(C₈H₃NO₆)·H₂O
M_r = 511.01
Monoclinic, P 2₁ /c
a = 7.692 (2) Å
b = 12.229 (3) Å
c = 16.379 (4) Å
β = 102.100 (4)°
V = 1506.5 (7) Å³
Z = 4
Mo Kα radiation
μ = 2.64 mm⁻¹
T = 298 K
0.11 × 0.10 × 0.08 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.760, T_max = 0.817
7118 measured reflections
2627 independent reflections
2500 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.114
S = 1.22
2627 reflections
204 parameters
H-atom parameters constrained
Δρ_max = 0.97 e Å⁻³
Δρ_min = −0.98 e Å⁻³

Table 1
Selected bond lengths (Å)

Ag1—N1	2.112 (5)
Ag1—N2	2.105 (5)
Ag2—N3	2.088 (4)
Ag2—N4	2.094 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O1ⁱ	0.85	1.96	2.807 (5)	177
O1W—H1WB⋯O3	0.85	1.88	2.684 (5)	156
N1—H1B⋯O4ⁱⁱ	0.89	2.35	3.082 (6)	140
N1—H1C⋯O1	0.89	2.10	2.905 (6)	149
N2—H2A⋯O3ⁱⁱⁱ	0.89	2.09	2.954 (6)	164
N2—H2B⋯O4^iv	0.89	2.36	3.218 (6)	163
N2—H2C⋯O1Wⁱⁱ	0.89	2.28	3.059 (6)	147
N2—H2C⋯O6	0.89	2.57	2.990 (6)	110
N3—H3A⋯O2^v	0.89	2.08	2.937 (6)	163
N3—H3B⋯O1^iv	0.89	2.06	2.930 (6)	167
N3—H3C⋯O4	0.89	2.02	2.901 (5)	173
N4—H4A⋯O4^vi	0.89	2.23	3.088 (6)	163
N4—H4B⋯O3^vii	0.89	2.14	3.024 (6)	176
N4—H4C⋯O2ⁱⁱ	0.89	2.15	3.036 (5)	175
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z+1; (iii) x, y+1, z; (iv) -x+1, -y+1, -z+1; (v) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (vi) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (vii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999 ) and SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810007725/hy2282sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810007725/hy2282Isup2.hkl

checkCIF report

Comment top

Renaissance in crystal engineering and supramolecular chemistry is due to the diverse and aesthetic structural topologies and potential use in optical, electrical, catalytic, gas storage and even drug delivery as functional solid materials (Batten & Robson, 1998; Blake et al., 1999; Yaghi et al., 2003). In addition to coordination bonds, noncovalent interactions such as hydrogen bond, π–π stacking, C—H···π, anion···π, cation···π and lone-pair(lp)···π interactions between molecules also play a pivotal role in the stability of molecule packing and govern the physicochemical properties of molecular systems in the condensed phase (Mooibroek et al., 2006; Nishio et al., 1998). Although Ag^I ion under ammoniacal conditions can form {[Ag(NH₃)₂]⁺}_n (n = 1 or 2) (Zheng et al., 2007), which can be stabilized by supramolecular interactions, only limited [Ag(NH₃)₂]-containing compounds were documented due to the weak Ag—N_ammine coordination bond (You et al., 2004; Zheng et al., 2002). Recently, we have pursued systematic investigations about the self-assembly of Ag^I ion with different bipodal N-donor ligands and multicarboxylates under ammoniacal conditions (Sun, Luo, Huang et al., 2009; Sun, Luo, Xu et al., 2009; Sun, Luo, Zhang et al., 2009). In an attempt to exploit the Ag^I/aminopyrazine/H₂nipa system (H₂nipa = 5-nitroisophthalic acid), we surprisingly obtained the title compound.

The title compound comprises two [Ag(NH₃)₂]⁺ cations, one nipa anion and one uncoordinated water molecule in the asymmetric unit (Fig. 1). Each Ag^I ion is in an almost linear coordination environment, coordinated by two ammonia molecules, forming a cationic [Ag(NH₃)₂]⁺ monomer. The Ag—N bond lengths range from 2.088 (4) to 2.112 (5) Å (Table 1), which are comparable to the corresponding values observed in other silver(I) compounds (You & Zhu, 2004). The N1—Ag1—N2 [169.90 (19)°] and N3—Ag2—N4 [174.05 (16)°] angles deviate from the ideal 180°, as a result of weak interactions between the Ag^I ions and water molecules. The Ag1···O1Wⁱⁱⁱ and Ag2···O1W^v distances are 2.725 (4) and 2.985 (4) Å, respectively, which suggest anything other than a secondary interaction [symmetry codes: (iii) x, y+1, z; (v) x+1, -y+1/2, z+1/2]. The shortest centroid–centroid distance between neighboring phenyl rings of nipa anions is 3.975 (3) Å, with a large slippage of 2.129 Å, which suggests the existence of a weak offset π–π stacking interaction. On the other hand, one striking feature of the title compound is an lp···π interaction (Biswas et al., 2009; Egli & Arkhel, 2007). A weak lp···π interaction is observed between the nitro O5 atom and phenyl ring of the nipa anion. The distance between the ring centroid and O5 atom is 3.401 (4) Å. This lp(O)···π interaction distance falls in the range of few experimental examples so far reported (Rahman et al., 2003). The angle θ (which corresponds to the angle between the O atom, the ring centroid and the aromatic plane) is 83.7 (3)°, reflecting a significant lp···π interaction. Every two nipa anions arrange in a parallel manner, forming a dimer through lp(O)···π interactions, and the neighboring dimers pack togther through weak π–π stacking interactions into columns running along the a axis (Fig. 2).

One of the ammonia molecules forms a bifurcated hydrogen bond (Jeffrey et al., 1985) [N2–H2C···O1Wⁱⁱ and N2–H2C···O6, symmetry code: (ii) -x, -y+1, -z+1]. In addition, the [Ag(NH₃)₂]⁺ cations, nipa anions and water molecules interact via N—H···O and O—H···O hydrogen bonds (Table 2) [average N···O = 3.010 (6), O···O = 2.746 (5) Å] to consolidate the three-dimensional supramolecular network (Fig. 3).

Related literature top

For general background to crystal engineering and supramolecular chemistry, see: Batten & Robson (1998); Blake et al. (1999); Yaghi et al. (2003). For general background to non-covalent interactions, see: Biswas et al. (2009); Egli & Arkhel (2007); Jeffrey et al. (1985); Mooibroek et al. (2006); Nishio et al. (1998); Rahman et al. (2003). For related structures, see: Sun, Luo, Huang et al. (2009); Sun, Luo, Xu et al. (2009); Sun, Luo, Zhang et al. (2009); You & Zhu (2004); You et al. (2004); Zheng et al. (2002, 2007).

Experimental top

All reagents and solvents were used as obtained commercially without further purification. A mixture of Ag₂O (116 mg, 0.5 mmol), 2-aminopyrazine (95 mg, 1 mmol) and H₂nipa (211 mg, 1 mmol) were stirred in CH₃CN/H₂O mixed solvent (8 ml, v/v = 1:1). Then aqueous NH₃ solution (25%) was dropped into the mixture to give a clear solution under ultrasonic treatment. The resultant solution was allowed to evaporate slowly in darkness at room temperature for several days to give colorless crystals of the title compound (yield 61%). They were washed with a small volume of cold CH₃CN and diethyl ether. Analysis calculated for C₈H₁₇Ag₂N₅O₇: C 18.80, H 3.35, N 13.71%; found: C 18.86, H 3.39, N 13.64%.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999) and SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the coordination environment around the Ag^I center. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A ball-stick perspective view of the lp(O)···π (green dashed lines) and π–π (blue dashed lines) interactions in the title compound. H atoms and [Ag(NH₃)₂]⁺ cations have been omitted for clarity.
	Fig. 3. Perspective views of the three-dimensional supramolecular network incorporating N—H···O and O—H···O hydrogen bonds (dashed lines) viewed along two different directions.

Bis[diamminesilver(I)] 5-nitroisophthalate monohydrate top

Crystal data top

[Ag(NH₃)₂]₂(C₈H₃NO₆)·H₂O	F(000) = 1000
M_r = 511.01	D_x = 2.253 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4729 reflections
a = 7.692 (2) Å	θ = 5.1–57.2°
b = 12.229 (3) Å	µ = 2.64 mm⁻¹
c = 16.379 (4) Å	T = 298 K
β = 102.100 (4)°	Block, colorless
V = 1506.5 (7) Å³	0.11 × 0.10 × 0.08 mm
Z = 4

Data collection top

Oxford Diffraction Gemini S Ultra diffractometer	2627 independent reflections
Radiation source: sealed tube	2500 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 16.1903 pixels mm^-1	θ_max = 25.0°, θ_min = 2.1°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −8→14
T_min = 0.760, T_max = 0.817	l = −17→19
7118 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.114	w = 1/[σ²(F_o²) + (0.0451P)² + 2.1461P] where P = (F_o² + 2F_c²)/3
S = 1.22	(Δ/σ)_max < 0.001
2627 reflections	Δρ_max = 0.97 e Å⁻³
204 parameters	Δρ_min = −0.98 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0264 (13)

Crystal data top

[Ag(NH₃)₂]₂(C₈H₃NO₆)·H₂O	V = 1506.5 (7) Å³
M_r = 511.01	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.692 (2) Å	µ = 2.64 mm⁻¹
b = 12.229 (3) Å	T = 298 K
c = 16.379 (4) Å	0.11 × 0.10 × 0.08 mm
β = 102.100 (4)°

Data collection top

Oxford Diffraction Gemini S Ultra diffractometer	2627 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	2500 reflections with I > 2σ(I)
T_min = 0.760, T_max = 0.817	R_int = 0.036
7118 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.22	Δρ_max = 0.97 e Å⁻³
2627 reflections	Δρ_min = −0.98 e Å⁻³
204 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ag1	0.01233 (6)	0.87015 (4)	0.39354 (3)	0.0561 (2)
Ag2	0.56988 (5)	0.37352 (3)	0.78293 (3)	0.0444 (2)
C1	0.1106 (5)	0.4687 (4)	0.4096 (3)	0.0272 (9)
C2	0.1513 (6)	0.3606 (4)	0.4283 (3)	0.0277 (9)
H2	0.0955	0.3065	0.3922	0.033*
C3	0.2729 (5)	0.3307 (4)	0.4993 (3)	0.0273 (9)
C4	0.3475 (6)	0.4110 (4)	0.5543 (3)	0.0294 (10)
H4	0.4278	0.3929	0.6032	0.035*
C5	0.3022 (6)	0.5176 (4)	0.5362 (3)	0.0281 (9)
C6	0.1878 (6)	0.5481 (4)	0.4639 (3)	0.0294 (10)
H6	0.1631	0.6216	0.4521	0.035*
C7	−0.0153 (6)	0.4982 (4)	0.3292 (3)	0.0308 (10)
C8	0.3273 (6)	0.2131 (4)	0.5152 (3)	0.0293 (10)
N1	−0.1928 (7)	0.8046 (4)	0.3002 (3)	0.0544 (12)
H1A	−0.1867	0.8333	0.2509	0.065*
H1B	−0.2977	0.8205	0.3120	0.065*
H1C	−0.1805	0.7323	0.2983	0.065*
N2	0.2262 (6)	0.9066 (4)	0.4929 (3)	0.0499 (11)
H2A	0.2441	0.9786	0.4954	0.060*
H2B	0.3239	0.8733	0.4846	0.060*
H2C	0.2011	0.8835	0.5406	0.060*
N3	0.7101 (6)	0.2725 (4)	0.7167 (3)	0.0411 (10)
H3A	0.7576	0.2171	0.7490	0.049*
H3B	0.7962	0.3108	0.7012	0.049*
H3C	0.6364	0.2466	0.6716	0.049*
N4	0.4096 (5)	0.4767 (4)	0.8378 (2)	0.0395 (10)
H4A	0.4737	0.5333	0.8615	0.047*
H4B	0.3677	0.4399	0.8764	0.047*
H4C	0.3192	0.5008	0.7988	0.047*
N5	0.3862 (6)	0.6021 (4)	0.5942 (2)	0.0358 (9)
O1	−0.0137 (5)	0.5948 (3)	0.3058 (2)	0.0405 (8)
O1W	−0.0469 (5)	0.0861 (3)	0.3572 (2)	0.0502 (9)
H1WA	−0.0315	0.0871	0.3073	0.060*
H1WB	0.0474	0.1189	0.3813	0.060*
O2	−0.1083 (5)	0.4259 (3)	0.2916 (2)	0.0502 (10)
O3	0.2508 (5)	0.1444 (3)	0.4657 (3)	0.0494 (10)
O4	0.4452 (5)	0.1927 (3)	0.5764 (2)	0.0412 (8)
O5	0.4957 (5)	0.5735 (3)	0.6553 (2)	0.0509 (10)
O6	0.3436 (6)	0.6952 (3)	0.5786 (2)	0.0567 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0498 (3)	0.0475 (3)	0.0734 (4)	−0.00206 (19)	0.0184 (2)	−0.0061 (2)
Ag2	0.0446 (3)	0.0460 (3)	0.0402 (3)	0.00187 (17)	0.00340 (18)	−0.00385 (17)
C1	0.027 (2)	0.030 (2)	0.025 (2)	0.0008 (18)	0.0062 (16)	0.0021 (18)
C2	0.032 (2)	0.026 (2)	0.024 (2)	−0.0037 (18)	0.0049 (17)	−0.0045 (17)
C3	0.024 (2)	0.028 (2)	0.030 (2)	0.0005 (18)	0.0057 (17)	0.0014 (19)
C4	0.030 (2)	0.031 (2)	0.027 (2)	0.0013 (19)	0.0049 (17)	0.0026 (19)
C5	0.030 (2)	0.028 (2)	0.027 (2)	−0.0044 (19)	0.0088 (17)	−0.0030 (18)
C6	0.028 (2)	0.029 (2)	0.032 (2)	0.0017 (19)	0.0104 (18)	0.0025 (19)
C7	0.030 (2)	0.028 (3)	0.034 (2)	0.005 (2)	0.0069 (18)	0.006 (2)
C8	0.031 (2)	0.027 (2)	0.031 (2)	0.0054 (19)	0.0082 (19)	0.0019 (19)
N1	0.061 (3)	0.048 (3)	0.055 (3)	0.006 (2)	0.016 (2)	0.001 (2)
N2	0.052 (3)	0.038 (3)	0.062 (3)	0.006 (2)	0.015 (2)	0.009 (2)
N3	0.038 (2)	0.038 (2)	0.043 (2)	−0.0028 (19)	−0.0014 (18)	−0.0036 (19)
N4	0.039 (2)	0.039 (2)	0.039 (2)	−0.0006 (19)	0.0032 (17)	0.0000 (19)
N5	0.042 (2)	0.035 (2)	0.031 (2)	−0.0080 (19)	0.0082 (18)	−0.0020 (18)
O1	0.044 (2)	0.0333 (19)	0.0391 (19)	0.0038 (16)	−0.0021 (15)	0.0113 (16)
O1W	0.045 (2)	0.059 (3)	0.043 (2)	0.0005 (19)	0.0004 (16)	−0.0007 (19)
O2	0.054 (2)	0.037 (2)	0.047 (2)	−0.0080 (18)	−0.0167 (17)	0.0017 (18)
O3	0.060 (2)	0.0287 (19)	0.049 (2)	0.0045 (17)	−0.0119 (18)	−0.0091 (17)
O4	0.0412 (18)	0.0344 (19)	0.0393 (18)	0.0044 (15)	−0.0112 (15)	0.0000 (15)
O5	0.060 (2)	0.046 (2)	0.039 (2)	−0.0077 (19)	−0.0089 (17)	−0.0042 (17)
O6	0.088 (3)	0.027 (2)	0.049 (2)	0.002 (2)	−0.001 (2)	−0.0022 (17)

Geometric parameters (Å, º) top

Ag1—N1	2.112 (5)	C7—O1	1.243 (6)
Ag1—N2	2.105 (5)	C8—O3	1.228 (6)
Ag2—N3	2.088 (4)	C8—O4	1.229 (5)
Ag2—N4	2.094 (4)	N1—H1A	0.8900
Ag1—O1Wⁱ	2.725 (4)	N1—H1B	0.8900
Ag2—O1Wⁱⁱ	2.985 (4)	N1—H1C	0.8900
C1—C6	1.367 (6)	N2—H2A	0.8900
C1—C2	1.378 (6)	N2—H2B	0.8900
C1—C7	1.505 (6)	N2—H2C	0.8900
C2—C3	1.380 (6)	N3—H3A	0.8900
C2—H2	0.9300	N3—H3B	0.8900
C3—C4	1.374 (6)	N3—H3C	0.8900
C3—C8	1.505 (6)	N4—H4A	0.8900
C4—C5	1.366 (6)	N4—H4B	0.8900
C4—H4	0.9300	N4—H4C	0.8900
C5—C6	1.370 (6)	N5—O6	1.198 (6)
C5—N5	1.460 (6)	N5—O5	1.217 (5)
C6—H6	0.9300	O1W—H1WA	0.8501
C7—O2	1.220 (6)	O1W—H1WB	0.8500

N2—Ag1—N1	169.90 (19)	O4—C8—C3	117.8 (4)
N3—Ag2—N4	174.05 (16)	Ag1—N1—H1A	109.5
N2—Ag1—O1Wⁱ	91.79 (15)	Ag1—N1—H1B	109.5
N1—Ag1—O1Wⁱ	98.31 (16)	H1A—N1—H1B	109.5
N3—Ag2—O1Wⁱⁱ	74.69 (14)	Ag1—N1—H1C	109.5
N4—Ag2—O1Wⁱⁱ	110.21 (14)	H1A—N1—H1C	109.5
C6—C1—C2	119.3 (4)	H1B—N1—H1C	109.5
C6—C1—C7	120.7 (4)	Ag1—N2—H2A	109.5
C2—C1—C7	119.9 (4)	Ag1—N2—H2B	109.5
C1—C2—C3	121.6 (4)	H2A—N2—H2B	109.5
C1—C2—H2	119.2	Ag1—N2—H2C	109.5
C3—C2—H2	119.2	H2A—N2—H2C	109.5
C4—C3—C2	118.7 (4)	H2B—N2—H2C	109.5
C4—C3—C8	120.4 (4)	Ag2—N3—H3A	109.5
C2—C3—C8	120.9 (4)	Ag2—N3—H3B	109.5
C5—C4—C3	119.1 (4)	H3A—N3—H3B	109.5
C5—C4—H4	120.4	Ag2—N3—H3C	109.5
C3—C4—H4	120.4	H3A—N3—H3C	109.5
C4—C5—C6	122.4 (4)	H3B—N3—H3C	109.5
C4—C5—N5	118.5 (4)	Ag2—N4—H4A	109.5
C6—C5—N5	119.0 (4)	Ag2—N4—H4B	109.5
C1—C6—C5	118.8 (4)	H4A—N4—H4B	109.5
C1—C6—H6	120.6	Ag2—N4—H4C	109.5
C5—C6—H6	120.6	H4A—N4—H4C	109.5
O2—C7—O1	125.1 (4)	H4B—N4—H4C	109.5
O2—C7—C1	118.0 (4)	O6—N5—O5	124.1 (4)
O1—C7—C1	116.8 (4)	O6—N5—C5	118.1 (4)
O3—C8—O4	124.7 (4)	O5—N5—C5	117.8 (4)
O3—C8—C3	117.5 (4)	H1WA—O1W—H1WB	99.3

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O1ⁱⁱⁱ	0.85	1.96	2.807 (5)	177
O1W—H1WB···O3	0.85	1.88	2.684 (5)	156
N1—H1B···O4^iv	0.89	2.35	3.082 (6)	140
N1—H1C···O1	0.89	2.10	2.905 (6)	149
N2—H2A···O3ⁱ	0.89	2.09	2.954 (6)	164
N2—H2B···O4^v	0.89	2.36	3.218 (6)	163
N2—H2C···O1W^iv	0.89	2.28	3.059 (6)	147
N2—H2C···O6	0.89	2.57	2.990 (6)	110
N3—H3A···O2ⁱⁱ	0.89	2.08	2.937 (6)	163
N3—H3B···O1^v	0.89	2.06	2.930 (6)	167
N3—H3C···O4	0.89	2.02	2.901 (5)	173
N4—H4A···O4^vi	0.89	2.23	3.088 (6)	163
N4—H4B···O3^vii	0.89	2.14	3.024 (6)	176
N4—H4C···O2^iv	0.89	2.15	3.036 (5)	175

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

Experimental details

Crystal data
Chemical formula	[Ag(NH₃)₂]₂(C₈H₃NO₆)·H₂O
M_r	511.01
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.692 (2), 12.229 (3), 16.379 (4)
β (°)	102.100 (4)
V (Å³)	1506.5 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.64
Crystal size (mm)	0.11 × 0.10 × 0.08

Data collection
Diffractometer	Oxford Diffraction Gemini S Ultra diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2006)
T_min, T_max	0.760, 0.817
No. of measured, independent and observed [I > 2σ(I)] reflections	7118, 2627, 2500
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.114, 1.22
No. of reflections	2627
No. of parameters	204
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.97, −0.98

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999) and SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Ag1—N1	2.112 (5)	Ag2—N3	2.088 (4)
Ag1—N2	2.105 (5)	Ag2—N4	2.094 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O1ⁱ	0.85	1.96	2.807 (5)	177
O1W—H1WB···O3	0.85	1.88	2.684 (5)	156
N1—H1B···O4ⁱⁱ	0.89	2.35	3.082 (6)	140
N1—H1C···O1	0.89	2.10	2.905 (6)	149
N2—H2A···O3ⁱⁱⁱ	0.89	2.09	2.954 (6)	164
N2—H2B···O4^iv	0.89	2.36	3.218 (6)	163
N2—H2C···O1Wⁱⁱ	0.89	2.28	3.059 (6)	147
N2—H2C···O6	0.89	2.57	2.990 (6)	110
N3—H3A···O2^v	0.89	2.08	2.937 (6)	163
N3—H3B···O1^iv	0.89	2.06	2.930 (6)	167
N3—H3C···O4	0.89	2.02	2.901 (5)	173
N4—H4A···O4^vi	0.89	2.23	3.088 (6)	163
N4—H4B···O3^vii	0.89	2.14	3.024 (6)	176
N4—H4C···O2ⁱⁱ	0.89	2.15	3.036 (5)	175

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

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Volume 66| Part 4| April 2010| Pages m406-m407

doi:10.1107/S1600536810007725

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