catena-Poly[[[aqua­(pyridine-4-carboxyl­ato-κN)silver(I)]-μ-hexa­methyl­ene­tetra­amine-κ2N:N′] dihydrate]

Sun, D.; Han, L.; Zang, H.

doi:10.1107/S1600536810050452

metal-organic compounds

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Volume 67| Part 1| January 2011| Page m47

https://doi.org/10.1107/S1600536810050452

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catena-Poly[[[aqua(pyridine-4-carboxylato-κN)silver(I)]-μ-hexamethylenetetraamine-κ²N:N′] dihydrate]

Dajun Sun,^a Liying Han ^b ^* and Hu Zang ^c

^aDepartment of Vascular Surgery, The China–Japan Union Hospital of Jilin University, Changchun 130033, People's Republic of China, ^bDepartment of Gynecology, The Second Hospital of Jilin University, Changchun 130041, People's Republic of China, and ^cDepartment of Orthopedics, The China–Japan Union Hospital of Jilin University, Changchun 130033, People's Republic of China
^*Correspondence e-mail: drhanly2010@163.com

(Received 23 November 2010; accepted 2 December 2010; online 8 December 2010)

In the title compound, {[Ag(C₆H₄NO₂)(C₆H₁₂N₄)(H₂O)]·2H₂O}_n, the Ag^I atom shows a distorted triangular pyramidal geometry,, formed by two N atoms from two hexamethylenetetraamine (hmt) ligands and one N atom from a pyridine-4-carboxylate (4-pdc) ligand and one water molecule. The hmt ligands bridge the Ag atoms, forming a chain along [001]. The carboxylate group of the 4-pdc ligand is uncoordinated. O—H⋯O hydrogen bonds between the water molecules and carboxylate groups stabilize the structure.

Related literature

For general background to the design and synthesis of coordination polymers, see: Eddaoudi et al. (2001 ).

Experimental

Crystal data

[Ag(C₆H₄NO₂)(C₆H₁₂N₄)(H₂O)]·2H₂O
M_r = 424.22
Orthorhombic, P n a 2₁
a = 11.8271 (5) Å
b = 13.2122 (5) Å
c = 10.2560 (4) Å
V = 1602.62 (11) Å³
Z = 4
Mo Kα radiation
μ = 1.29 mm⁻¹
T = 293 K
0.24 × 0.20 × 0.19 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.747, T_max = 0.792
7849 measured reflections
2380 independent reflections
2347 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.016
wR(F²) = 0.041
S = 1.08
2380 reflections
226 parameters
10 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.55 e Å⁻³
Absolute structure: Flack (1983 ), 876 Friedel pairs
Flack parameter: 0.01 (2)

Table 1
Selected bond lengths (Å)

Ag1—N1	2.287 (2)
Ag1—N2	2.256 (2)
Ag1—N5ⁱ	2.306 (2)
Ag1—O1W	2.673 (2)
Symmetry code: (i) $[-x, -y, z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1A⋯O2Wⁱⁱ	0.85 (3)	1.91 (3)	2.743 (3)	169 (3)
O1W—H1B⋯O1ⁱⁱⁱ	0.85 (1)	1.91 (2)	2.714 (2)	157 (3)
O2W—H2A⋯O2	0.84 (1)	1.88 (1)	2.722 (3)	173 (3)
O2W—H2B⋯O3W^iv	0.84 (3)	1.99 (3)	2.787 (3)	161 (3)
O3W—H3A⋯O1W^v	0.85 (1)	1.95 (1)	2.788 (3)	169 (3)
O3W—H3B⋯O1	0.85 (1)	1.89 (1)	2.728 (2)	169 (3)
Symmetry codes: (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (iii) $[-x+1, -y, z-{\script{1\over 2}}]$ ; (iv) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (v) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810050452/hy2384sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810050452/hy2384Isup2.hkl

checkCIF report

Comment top

The design and synthesis of coordination polymers have been a research field of rapid expansion not only because of their fascinating structures, but also owing to their interesting properties as new functional materials of tremendous potential applications in molecular recognition, ion-exchange, and catalysis for reactions (Eddaoudi et al., 2001). In this work, the reaction of pyridine-4-carboxylatic acid (4-Hpdc) and hexamethylenetetraamine (hmt) with Ag^I ion yielded a new coordination polymer.

As shown in Fig. 1, the asymmetric unit of the title compound contains one Ag^I atom, one 4-pdc ligand, one hmt ligand, one coordinated water molecule and two uncoordinated water molecules. The Ag1 atom shows a distorted triangle pyramidal geometry, completed by three N atoms from two hmt ligands and one 4-pdc ligand and one O atom from a water molecule. The hmt ligands bridge the Ag atoms, forming a one-dimensional chain. The carboxylate group of the 4-pdc ligand is uncoordinated. O—H···O hydrogen bonds between the water molecules and carboxylate groups stabilize the structure.

Related literature top

For general background to the design and synthesis of coordination polymers, see: Eddaoudi et al. (2001).

Experimental top

A mixture of 4-Hpdc (0.615 g, 0.5 mmol), Ag(NO₃)₂ (0.085 g, 0.5 mmol) and hmt (0.070 g, 0.5 mmol) in water was heated at 150°C in a Teflon-lined stainless steel autoclave for 5 d. The reaction system was then slowly cooled to room temperature. Crystals suitable for X-ray diffraction analysis were collected by filtration.

Structure description top

For general background to the design and synthesis of coordination polymers, see: Eddaoudi et al. (2001).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (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 asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (i) -x, -y, z+1/2].
	Fig. 2. View of the chain structure in the title compound.

catena-Poly[[[aqua(pyridine-4-carboxylato-κN)silver(I)]- µ-hexamethylenetetraamine-κ²N:N'] dihydrate] top

Crystal data top

[Ag(C₆H₄NO₂)(C₆H₁₂N₄)(H₂O)]·2H₂O	F(000) = 864
M_r = 424.22	D_x = 1.758 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2380 reflections
a = 11.8271 (5) Å	θ = 3.0–26.1°
b = 13.2122 (5) Å	µ = 1.29 mm⁻¹
c = 10.2560 (4) Å	T = 293 K
V = 1602.62 (11) Å³	Block, colorless
Z = 4	0.24 × 0.20 × 0.19 mm

Data collection top

Bruker APEX CCD diffractometer	2380 independent reflections
Radiation source: fine-focus sealed tube	2347 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
φ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→14
T_min = 0.747, T_max = 0.792	k = −15→15
7849 measured reflections	l = −10→12

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)] = 0.016	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.041	w = 1/[σ²(F_o²) + (0.0231P)² + 0.3127P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
2380 reflections	Δρ_max = 0.20 e Å⁻³
226 parameters	Δρ_min = −0.55 e Å⁻³
10 restraints	Absolute structure: Flack (1983), 876 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (2)

Crystal data top

[Ag(C₆H₄NO₂)(C₆H₁₂N₄)(H₂O)]·2H₂O	V = 1602.62 (11) Å³
M_r = 424.22	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 11.8271 (5) Å	µ = 1.29 mm⁻¹
b = 13.2122 (5) Å	T = 293 K
c = 10.2560 (4) Å	0.24 × 0.20 × 0.19 mm

Data collection top

Bruker APEX CCD diffractometer	2380 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2347 reflections with I > 2σ(I)
T_min = 0.747, T_max = 0.792	R_int = 0.016
7849 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.016	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.041	Δρ_max = 0.20 e Å⁻³
S = 1.08	Δρ_min = −0.55 e Å⁻³
2380 reflections	Absolute structure: Flack (1983), 876 Friedel pairs
226 parameters	Absolute structure parameter: 0.01 (2)
10 restraints

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

	x	y	z	U_iso*/U_eq
Ag1	0.128363 (13)	0.013803 (11)	0.15278 (4)	0.02268 (7)
C1	0.3975 (2)	0.04853 (19)	0.1327 (3)	0.0235 (6)
H1	0.3756	0.0961	0.0708	0.028*
C2	0.51160 (18)	0.03798 (16)	0.1607 (3)	0.0213 (5)
H2	0.5645	0.0788	0.1190	0.026*
C3	0.5467 (2)	−0.03375 (17)	0.2511 (2)	0.0180 (5)
C4	0.4633 (2)	−0.09081 (18)	0.3108 (3)	0.0226 (5)
H4	0.4826	−0.1395	0.3724	0.027*
C5	0.3513 (2)	−0.0753 (2)	0.2786 (3)	0.0253 (6)
H5	0.2968	−0.1145	0.3200	0.030*
C6	0.6705 (2)	−0.04864 (19)	0.2834 (2)	0.0195 (5)
C7	0.1034 (2)	−0.1856 (2)	−0.0106 (3)	0.0232 (6)
H7A	0.1690	−0.1589	−0.0556	0.028*
H7B	0.1299	−0.2228	0.0651	0.028*
C8	−0.0697 (2)	−0.14419 (19)	0.0997 (2)	0.0214 (5)
H8A	−0.0454	−0.1812	0.1764	0.026*
H8B	−0.1189	−0.0898	0.1281	0.026*
C9	−0.0568 (2)	−0.29341 (18)	−0.0278 (3)	0.0298 (6)
H9A	−0.0977	−0.3395	−0.0842	0.036*
H9B	−0.0321	−0.3312	0.0482	0.036*
C10	0.0045 (2)	−0.19809 (17)	−0.2111 (2)	0.0216 (5)
H10A	−0.0355	−0.2433	−0.2696	0.026*
H10B	0.0696	−0.1715	−0.2573	0.026*
C11	−0.0086 (2)	−0.04628 (17)	−0.0847 (3)	0.0188 (5)
H11A	−0.0572	0.0093	−0.0586	0.023*
H11B	0.0560	−0.0179	−0.1301	0.023*
C12	−0.1700 (2)	−0.15591 (19)	−0.1010 (3)	0.0207 (5)
H12A	−0.2195	−0.1012	−0.0741	0.025*
H12B	−0.2126	−0.2005	−0.1579	0.025*
N1	0.31739 (18)	−0.00721 (15)	0.1914 (2)	0.0226 (6)
N2	0.03133 (16)	−0.10028 (15)	0.0333 (2)	0.0175 (4)
N3	0.04299 (17)	−0.25501 (15)	−0.0976 (2)	0.0238 (4)
N4	−0.13283 (16)	−0.21224 (17)	0.0138 (2)	0.0225 (5)
N5	−0.07120 (15)	−0.11312 (15)	−0.1745 (2)	0.0165 (4)
O1	0.69699 (14)	−0.13139 (13)	0.33372 (19)	0.0263 (4)
O2	0.73760 (15)	0.02175 (13)	0.2588 (2)	0.0294 (5)
O1W	0.11516 (14)	0.16451 (15)	−0.0205 (2)	0.0254 (4)
H1A	0.145 (2)	0.2117 (19)	0.024 (3)	0.038*
H1B	0.161 (2)	0.147 (2)	−0.080 (2)	0.038*
O2W	0.73929 (16)	0.19124 (15)	0.1080 (2)	0.0344 (5)
H2A	0.736 (2)	0.1415 (17)	0.159 (2)	0.052*
H2B	0.777 (3)	0.176 (2)	0.042 (2)	0.052*
O3W	0.60916 (15)	−0.31522 (14)	0.4000 (3)	0.0330 (5)
H3A	0.5402 (12)	−0.313 (2)	0.423 (3)	0.049*
H3B	0.629 (2)	−0.2569 (14)	0.373 (4)	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.01850 (10)	0.02679 (10)	0.02274 (11)	−0.00070 (6)	−0.00291 (10)	−0.00824 (17)
C1	0.0231 (11)	0.0237 (11)	0.0236 (19)	0.0030 (9)	−0.0032 (12)	0.0047 (12)
C2	0.0200 (10)	0.0214 (10)	0.0226 (12)	−0.0030 (8)	0.0014 (14)	0.0042 (15)
C3	0.0193 (12)	0.0163 (11)	0.0185 (13)	0.0030 (9)	−0.0024 (10)	−0.0034 (10)
C4	0.0203 (12)	0.0220 (12)	0.0256 (14)	0.0024 (9)	0.0013 (11)	0.0062 (11)
C5	0.0201 (12)	0.0263 (14)	0.0295 (15)	−0.0025 (10)	0.0028 (11)	0.0048 (12)
C6	0.0177 (12)	0.0225 (12)	0.0184 (13)	0.0003 (10)	0.0004 (10)	0.0004 (10)
C7	0.0202 (12)	0.0234 (14)	0.0262 (16)	0.0054 (10)	−0.0018 (12)	−0.0043 (12)
C8	0.0206 (12)	0.0248 (13)	0.0188 (12)	−0.0023 (10)	0.0012 (10)	0.0021 (10)
C9	0.0414 (16)	0.0176 (13)	0.0305 (15)	−0.0053 (11)	−0.0100 (13)	0.0024 (11)
C10	0.0216 (12)	0.0223 (12)	0.0208 (13)	0.0025 (9)	−0.0006 (11)	−0.0039 (10)
C11	0.0179 (12)	0.0157 (10)	0.0228 (13)	−0.0002 (9)	0.0000 (10)	0.0016 (10)
C12	0.0154 (12)	0.0257 (13)	0.0208 (13)	−0.0046 (10)	−0.0008 (11)	0.0032 (11)
N1	0.0158 (10)	0.0237 (10)	0.0284 (16)	0.0010 (8)	−0.0010 (9)	−0.0004 (8)
N2	0.0132 (9)	0.0191 (10)	0.0202 (11)	0.0020 (8)	−0.0010 (8)	−0.0002 (8)
N3	0.0290 (11)	0.0179 (10)	0.0244 (11)	0.0055 (9)	−0.0075 (10)	−0.0041 (9)
N4	0.0232 (11)	0.0252 (12)	0.0190 (12)	−0.0077 (8)	−0.0014 (9)	0.0053 (9)
N5	0.0150 (10)	0.0167 (10)	0.0178 (11)	−0.0032 (8)	0.0000 (8)	0.0014 (8)
O1	0.0186 (8)	0.0235 (9)	0.0366 (11)	−0.0002 (7)	−0.0035 (8)	0.0104 (8)
O2	0.0190 (9)	0.0265 (10)	0.0427 (13)	−0.0057 (7)	−0.0055 (9)	0.0098 (8)
O1W	0.0196 (9)	0.0265 (11)	0.0300 (12)	−0.0025 (7)	0.0035 (8)	−0.0021 (9)
O2W	0.0317 (10)	0.0319 (10)	0.0396 (12)	0.0047 (8)	0.0038 (9)	0.0147 (8)
O3W	0.0219 (9)	0.0206 (10)	0.0564 (15)	−0.0012 (7)	−0.0013 (10)	0.0072 (10)

Geometric parameters (Å, º) top

Ag1—N1	2.287 (2)	C8—H8B	0.9700
Ag1—N2	2.256 (2)	C9—N4	1.463 (3)
Ag1—N5ⁱ	2.306 (2)	C9—N3	1.470 (4)
Ag1—O1W	2.673 (2)	C9—H9A	0.9700
C1—N1	1.342 (3)	C9—H9B	0.9700
C1—C2	1.387 (3)	C10—N3	1.459 (3)
C1—H1	0.9300	C10—N5	1.484 (3)
C2—C3	1.390 (4)	C10—H10A	0.9700
C2—H2	0.9300	C10—H10B	0.9700
C3—C4	1.384 (3)	C11—N5	1.476 (3)
C3—C6	1.513 (3)	C11—N2	1.482 (3)
C4—C5	1.380 (3)	C11—H11A	0.9700
C4—H4	0.9300	C11—H11B	0.9700
C5—N1	1.330 (3)	C12—N4	1.461 (3)
C5—H5	0.9300	C12—N5	1.501 (3)
C6—O2	1.249 (3)	C12—H12A	0.9700
C6—O1	1.249 (3)	C12—H12B	0.9700
C7—N3	1.465 (3)	O1W—H1A	0.85 (3)
C7—N2	1.483 (3)	O1W—H1B	0.85 (1)
C7—H7A	0.9700	O2W—H2A	0.84 (1)
C7—H7B	0.9700	O2W—H2B	0.84 (3)
C8—N4	1.464 (3)	O3W—H3A	0.85 (1)
C8—N2	1.492 (3)	O3W—H3B	0.85 (1)
C8—H8A	0.9700

N2—Ag1—N1	120.67 (7)	N3—C10—N5	112.10 (19)
N2—Ag1—N5ⁱ	130.41 (7)	N3—C10—H10A	109.2
N1—Ag1—N5ⁱ	102.86 (7)	N5—C10—H10A	109.2
N2—Ag1—O1W	96.13 (7)	N3—C10—H10B	109.2
N1—Ag1—O1W	105.23 (6)	N5—C10—H10B	109.2
N5ⁱ—Ag1—O1W	94.00 (7)	H10A—C10—H10B	107.9
N1—C1—C2	122.6 (3)	N5—C11—N2	112.42 (18)
N1—C1—H1	118.7	N5—C11—H11A	109.1
C2—C1—H1	118.7	N2—C11—H11A	109.1
C1—C2—C3	119.8 (2)	N5—C11—H11B	109.1
C1—C2—H2	120.1	N2—C11—H11B	109.1
C3—C2—H2	120.1	H11A—C11—H11B	107.9
C4—C3—C2	116.9 (2)	N4—C12—N5	111.27 (19)
C4—C3—C6	121.5 (2)	N4—C12—H12A	109.4
C2—C3—C6	121.6 (2)	N5—C12—H12A	109.4
C5—C4—C3	119.8 (2)	N4—C12—H12B	109.4
C5—C4—H4	120.1	N5—C12—H12B	109.4
C3—C4—H4	120.1	H12A—C12—H12B	108.0
N1—C5—C4	123.4 (2)	C5—N1—C1	117.3 (2)
N1—C5—H5	118.3	C5—N1—Ag1	119.57 (17)
C4—C5—H5	118.3	C1—N1—Ag1	123.05 (17)
O2—C6—O1	125.1 (2)	C11—N2—C7	107.5 (2)
O2—C6—C3	118.3 (2)	C11—N2—C8	107.76 (18)
O1—C6—C3	116.6 (2)	C7—N2—C8	107.63 (19)
N3—C7—N2	112.35 (19)	C11—N2—Ag1	106.48 (14)
N3—C7—H7A	109.1	C7—N2—Ag1	112.35 (14)
N2—C7—H7A	109.1	C8—N2—Ag1	114.77 (15)
N3—C7—H7B	109.1	C10—N3—C7	108.4 (2)
N2—C7—H7B	109.1	C10—N3—C9	108.41 (19)
H7A—C7—H7B	107.9	C7—N3—C9	108.1 (2)
N4—C8—N2	111.90 (19)	C12—N4—C9	108.8 (2)
N4—C8—H8A	109.2	C12—N4—C8	109.0 (2)
N2—C8—H8A	109.2	C9—N4—C8	108.17 (19)
N4—C8—H8B	109.2	C11—N5—C10	107.94 (17)
N2—C8—H8B	109.2	C11—N5—C12	107.64 (19)
H8A—C8—H8B	107.9	C10—N5—C12	108.15 (19)
N4—C9—N3	112.48 (19)	C11—N5—Ag1ⁱⁱ	106.63 (14)
N4—C9—H9A	109.1	C10—N5—Ag1ⁱⁱ	114.39 (15)
N3—C9—H9A	109.1	C12—N5—Ag1ⁱⁱ	111.83 (14)
N4—C9—H9B	109.1	H1A—O1W—H1B	108.9 (15)
N3—C9—H9B	109.1	H2A—O2W—H2B	110.2 (16)
H9A—C9—H9B	107.8	H3A—O3W—H3B	108.7 (15)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O2Wⁱⁱⁱ	0.85 (3)	1.91 (3)	2.743 (3)	169 (3)
O1W—H1B···O1^iv	0.85 (1)	1.91 (2)	2.714 (2)	157 (3)
O2W—H2A···O2	0.84 (1)	1.88 (1)	2.722 (3)	173 (3)
O2W—H2B···O3W^v	0.84 (3)	1.99 (3)	2.787 (3)	161 (3)
O3W—H3A···O1W^vi	0.85 (1)	1.95 (1)	2.788 (3)	169 (3)
O3W—H3B···O1	0.85 (1)	1.89 (1)	2.728 (2)	169 (3)

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

Experimental details

Crystal data
Chemical formula	[Ag(C₆H₄NO₂)(C₆H₁₂N₄)(H₂O)]·2H₂O
M_r	424.22
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	293
a, b, c (Å)	11.8271 (5), 13.2122 (5), 10.2560 (4)
V (Å³)	1602.62 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.29
Crystal size (mm)	0.24 × 0.20 × 0.19

Data collection
Diffractometer	Bruker APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.747, 0.792
No. of measured, independent and observed [I > 2σ(I)] reflections	7849, 2380, 2347
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.016, 0.041, 1.08
No. of reflections	2380
No. of parameters	226
No. of restraints	10
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.55
Absolute structure	Flack (1983), 876 Friedel pairs
Absolute structure parameter	0.01 (2)

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Ag1—N1	2.287 (2)	Ag1—N5ⁱ	2.306 (2)
Ag1—N2	2.256 (2)	Ag1—O1W	2.673 (2)

Symmetry code: (i) −x, −y, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O2Wⁱⁱ	0.85 (3)	1.91 (3)	2.743 (3)	169 (3)
O1W—H1B···O1ⁱⁱⁱ	0.85 (1)	1.91 (2)	2.714 (2)	157 (3)
O2W—H2A···O2	0.84 (1)	1.88 (1)	2.722 (3)	173 (3)
O2W—H2B···O3W^iv	0.84 (3)	1.99 (3)	2.787 (3)	161 (3)
O3W—H3A···O1W^v	0.85 (1)	1.95 (1)	2.788 (3)	169 (3)
O3W—H3B···O1	0.85 (1)	1.89 (1)	2.728 (2)	169 (3)

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

Acknowledgements

The authors thank the China–Japan Union Hospital of Jilin University for supporting this work.

References

Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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