Poly[[μ2-1,4-bis­(3-pyridylmeth­oxy)benzene-hemi-μ2-fumarato-silver(I)] monohydrate]

Li, S.-L.; Bai, H.-Y.; Yang, J.

doi:10.1107/S1600536807054591

Poly[[μ₂-1,4-bis(3-pyridylmethoxy)benzene-hemi-μ₂-fumarato-silver(I)] monohydrate]

The asymmetric unit of the title structure, {[Ag(C₁₈H₁₆N₂O₂)(C₄H₂O₄)_0.5]·H₂O}_n, contains one Ag^I cation, one 1,4-bis(3-pyridylmethoxy)benzene (L) ligand, half of a fumarate ligand and one solvent water molecule. The Ag^I ion is in a distorted tetrahedral coordination geometry. Each L ligand bridges two symmetry-related Ag^I cations to form extended one-dimensional chains, which are, in turn, bridged by fumarate ligands to create chains of rings. The solvent water molecules donate hydrogen bonds to the carboxylate O atoms of fumarate ligands, generating a two-dimensional supramolecular structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054591/lh2537sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054591/lh2537Isup2.hkl Contains datablock I

CCDC reference: 672595

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Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.034
wR factor = 0.107
Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.06
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          4
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C19
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.10

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Ag1         (9)       0.76
PLAT804_ALERT_5_G ARU-Pack Problem in PLATON Analysis ............         10 Times
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3

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

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

Comment top

The design and synthesis of supramolecular complexes exhibiting novel structures and properties has provided exciting new prospects for chemists (Fujita et al., 1995; Yaghi et al., 1995; Zaworotko & Moulton, 2001). Among various supramolecular compounds, Ag(I) compounds are attractive because of their diverse structural types (Corespo et al., 1998). In this paper, we isolated a new Ag supramolecular compound, {[Ag(L)(fum)_0.5]^.H₂O}_n, constructed using 1,4-bis(pyridin-3-ylmethoxy)benzene (L) and fumarate (fum) ligands.

In the title structure, each Ag^I cation is four-coordinated and shows a tetrahedral geometry, surrounded by two N atoms from different L ligands and two carboxylate oxygen atoms from different fum anions (Fig. 1). The dihedral angle between two pyridine rings in the same L ligand is 23.6 (5)°. All bond distances and angles are normal (Allen et al., 1987). The L ligands exhibit bis-monodentate coordination modes and links Ag^I cations to generate an extended chain, which is further linked by fumarate anions to generate a double chainlike structure (Fig. 2). The lattice water molecules donate hydrogen bonds to carboxylate oxygen atoms of fumarate anions from adjacent double-chains, thus forming an intereting two-dimensional supramolecular structure (Fig. 3).

Related literature top

For related literature, see: Allen et al. (1987); Fujita et al. (1995); Yaghi et al. (1995; Zaworotko & Moulton (2001); Corespo et al. (1998).

Experimental top

A mixture of L (0.30 g, 1 mmol), AgNO₃ (0.17 g, 1 mmol), fumaric acid (0.12 g, 1 mmol) and H₂O (10 ml) was stirred for 1 h and then sealed in a 25 ml Teflonlined stainless steel container. The container was heated to 423 K and held at that temperature for 72 h, then cooled to room temperature at a rate of 10 K h^-1. Colorless crystals of the title compound were collected in 56% yield based on Ag.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

	Fig. 1. View of the coordination enviroment of an Ag atom. Displacement ellipsoids are drawn at the 30% probability level. Symmetry codes: (i) x + 2, y - 1, z - 1; (ii) 1 - x, -y, 1 - z.
	Fig. 2. Ball-stick representation of part of an extended chain of rings.
	Fig. 3. Ball-stick representation of part of the two-dimensional supramolecular structure. Hydrogen bonds are shown as dashed lines.

Poly[[µ₂-1,4-bis(3-pyridylmethoxy)benzene-hemi-µ₂-fumarato-silver(I)] hydrate] top

Crystal data top

[Ag(C₁₈H₁₆N₂O₂)(C₄H₂O₄)_0.5]·H₂O	Z = 2
M_r = 475.24	F(000) = 480
Triclinic, P1	D_x = 1.694 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 8.5730 (8) Å	Cell parameters from 4127 reflections
b = 9.7120 (9) Å	θ = 1.8–28.5°
c = 12.0990 (11) Å	µ = 1.12 mm⁻¹
α = 88.845 (2)°	T = 293 K
β = 71.867 (1)°	Block, colorless
γ = 77.047 (2)°	0.42 × 0.36 × 0.35 mm
V = 931.65 (15) Å³

Data collection top

Bruker APEX CCD area-detector diffractometer	4127 independent reflections
Radiation source: fine-focus sealed tube	3629 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ω scans	θ_max = 28.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.632, T_max = 0.676	k = −12→12
5611 measured reflections	l = −15→8

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0611P)² + 0.3593P] where P = (F_o² + 2F_c²)/3
4127 reflections	(Δ/σ)_max = 0.001
259 parameters	Δρ_max = 1.17 e Å⁻³
3 restraints	Δρ_min = −0.57 e Å⁻³

Crystal data top

[Ag(C₁₈H₁₆N₂O₂)(C₄H₂O₄)_0.5]·H₂O	γ = 77.047 (2)°
M_r = 475.24	V = 931.65 (15) Å³
Triclinic, P1	Z = 2
a = 8.5730 (8) Å	Mo Kα radiation
b = 9.7120 (9) Å	µ = 1.12 mm⁻¹
c = 12.0990 (11) Å	T = 293 K
α = 88.845 (2)°	0.42 × 0.36 × 0.35 mm
β = 71.867 (1)°

Data collection top

Bruker APEX CCD area-detector diffractometer	4127 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3629 reflections with I > 2σ(I)
T_min = 0.632, T_max = 0.676	R_int = 0.018
5611 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	3 restraints
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 1.17 e Å⁻³
4127 reflections	Δρ_min = −0.57 e Å⁻³
259 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	0.64106 (3)	0.45095 (3)	0.55161 (2)	0.04642 (11)
C1	0.4381 (4)	0.4066 (3)	0.8046 (3)	0.0479 (8)
H1	0.5187	0.3215	0.7871	0.058*
C2	0.3196 (5)	0.4286 (4)	0.9124 (3)	0.0547 (9)
H2	0.3224	0.3613	0.9680	0.066*
C3	0.1954 (4)	0.5524 (4)	0.9376 (3)	0.0476 (7)
H3	0.1127	0.5687	1.0101	0.057*
C4	0.1949 (3)	0.6511 (3)	0.8549 (3)	0.0352 (6)
C5	0.3232 (3)	0.6225 (3)	0.7493 (3)	0.0362 (6)
H5	0.3262	0.6902	0.6937	0.043*
C6	0.0622 (4)	0.7879 (3)	0.8736 (3)	0.0391 (6)
H6A	0.1143	0.8682	0.8640	0.047*
H6B	0.0016	0.7916	0.8175	0.047*
C7	−0.1839 (4)	0.9076 (3)	1.0236 (3)	0.0416 (7)
C8	−0.2800 (4)	0.9094 (3)	1.1393 (3)	0.0470 (8)
H8	−0.2509	0.8372	1.1858	0.056*
C9	−0.4204 (4)	1.0199 (3)	1.1857 (3)	0.0448 (7)
H9	−0.4861	1.0209	1.2631	0.054*
C10	−0.4615 (4)	1.1267 (3)	1.1173 (3)	0.0378 (6)
C11	−0.3624 (4)	1.1257 (3)	1.0023 (3)	0.0427 (7)
H11	−0.3894	1.1998	0.9566	0.051*
C12	−0.2235 (4)	1.0157 (3)	0.9544 (3)	0.0418 (7)
H12	−0.1581	1.0148	0.8769	0.050*
C13	−0.7012 (4)	1.2405 (3)	1.2734 (3)	0.0409 (7)
H13A	−0.6349	1.2422	1.3252	0.049*
H13B	−0.7448	1.1556	1.2856	0.049*
C14	−0.8441 (3)	1.3692 (3)	1.2985 (3)	0.0354 (6)
C15	−0.9936 (3)	1.3643 (3)	1.3841 (3)	0.0356 (6)
H15	−1.0021	1.2801	1.4208	0.043*
C16	−0.8321 (4)	1.4946 (3)	1.2444 (3)	0.0444 (7)
H16	−0.7342	1.5014	1.1858	0.053*
C17	−0.9688 (4)	1.6107 (4)	1.2789 (3)	0.0515 (8)
H17	−0.9628	1.6967	1.2444	0.062*
C18	−1.1126 (4)	1.5963 (3)	1.3645 (3)	0.0457 (7)
H18	−1.2037	1.6740	1.3870	0.055*
C19	0.6094 (4)	0.1537 (3)	0.5074 (3)	0.0428 (7)
C20	0.5740 (4)	0.0108 (3)	0.4968 (3)	0.0416 (7)
H20	0.6633	−0.0679	0.4847	0.050*
N1	0.4431 (3)	0.5020 (3)	0.7234 (2)	0.0388 (5)
N2	−1.1269 (3)	1.4750 (3)	1.4167 (2)	0.0372 (5)
O1	0.7521 (4)	0.1564 (3)	0.5123 (4)	0.0778 (10)
O2	0.4997 (3)	0.2597 (2)	0.5080 (3)	0.0596 (7)
O3	−0.0494 (3)	0.7919 (2)	0.9878 (2)	0.0562 (7)
O4	−0.5989 (3)	1.2410 (2)	1.15538 (19)	0.0470 (5)
O1W	1.0451 (6)	−0.0306 (5)	0.3447 (3)	0.0956 (12)
H1A	1.107 (6)	−0.084 (7)	0.378 (5)	0.143*
H1B	0.946 (3)	−0.015 (8)	0.392 (5)	0.143*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.02882 (14)	0.05097 (17)	0.04432 (17)	−0.00020 (10)	0.00425 (10)	−0.00846 (11)
C1	0.0378 (16)	0.0375 (15)	0.0535 (19)	0.0032 (12)	−0.0014 (14)	−0.0017 (14)
C2	0.0462 (18)	0.0487 (18)	0.051 (2)	0.0015 (15)	0.0014 (15)	0.0091 (15)
C3	0.0387 (16)	0.0505 (18)	0.0394 (16)	−0.0026 (14)	0.0027 (13)	−0.0011 (13)
C4	0.0270 (13)	0.0354 (14)	0.0377 (15)	−0.0021 (11)	−0.0054 (11)	−0.0094 (11)
C5	0.0308 (13)	0.0347 (14)	0.0372 (15)	−0.0031 (11)	−0.0051 (12)	−0.0056 (11)
C6	0.0317 (14)	0.0396 (14)	0.0357 (15)	0.0029 (11)	−0.0032 (12)	−0.0101 (11)
C7	0.0293 (14)	0.0362 (14)	0.0451 (17)	0.0034 (11)	0.0011 (12)	−0.0083 (12)
C8	0.0381 (16)	0.0410 (16)	0.0443 (17)	0.0069 (13)	0.0009 (14)	0.0013 (13)
C9	0.0352 (15)	0.0450 (16)	0.0370 (16)	0.0042 (13)	0.0036 (13)	−0.0042 (13)
C10	0.0260 (13)	0.0372 (14)	0.0393 (15)	0.0046 (11)	−0.0023 (11)	−0.0095 (11)
C11	0.0346 (15)	0.0451 (16)	0.0386 (16)	0.0049 (12)	−0.0072 (13)	−0.0017 (13)
C12	0.0309 (14)	0.0505 (17)	0.0320 (14)	0.0004 (12)	0.0010 (12)	−0.0076 (12)
C13	0.0269 (13)	0.0400 (15)	0.0434 (16)	0.0025 (11)	−0.0002 (12)	−0.0058 (12)
C14	0.0253 (12)	0.0361 (14)	0.0371 (15)	0.0008 (10)	−0.0038 (11)	−0.0090 (11)
C15	0.0259 (13)	0.0349 (13)	0.0384 (15)	−0.0008 (10)	−0.0031 (11)	−0.0072 (11)
C16	0.0296 (14)	0.0473 (17)	0.0466 (17)	−0.0040 (12)	−0.0017 (13)	−0.0006 (13)
C17	0.0450 (18)	0.0400 (16)	0.057 (2)	−0.0034 (14)	−0.0036 (16)	0.0044 (14)
C18	0.0321 (15)	0.0407 (16)	0.0528 (19)	0.0047 (12)	−0.0058 (14)	−0.0073 (13)
C19	0.0439 (17)	0.0377 (15)	0.0421 (17)	−0.0125 (13)	−0.0046 (13)	0.0008 (12)
C20	0.0426 (16)	0.0311 (13)	0.0450 (17)	−0.0042 (12)	−0.0079 (14)	0.0014 (12)
N1	0.0284 (11)	0.0365 (12)	0.0400 (13)	−0.0002 (9)	0.0010 (10)	−0.0059 (10)
N2	0.0257 (11)	0.0378 (12)	0.0397 (13)	0.0001 (9)	−0.0027 (10)	−0.0107 (10)
O1	0.0632 (18)	0.0588 (17)	0.124 (3)	−0.0218 (14)	−0.043 (2)	0.0142 (18)
O2	0.0475 (14)	0.0339 (11)	0.0852 (19)	−0.0040 (10)	−0.0071 (13)	−0.0046 (11)
O3	0.0423 (13)	0.0443 (12)	0.0509 (14)	0.0131 (10)	0.0132 (11)	0.0001 (10)
O4	0.0330 (11)	0.0467 (12)	0.0403 (12)	0.0127 (9)	0.0029 (9)	−0.0047 (9)
O1W	0.093 (3)	0.109 (3)	0.073 (2)	−0.005 (2)	−0.022 (2)	0.010 (2)

Geometric parameters (Å, º) top

Ag1—N2ⁱ	2.202 (2)	C10—O4	1.388 (3)
Ag1—N1	2.217 (2)	C11—C12	1.386 (4)
Ag1—O2	2.577 (3)	C11—H11	0.9300
Ag1—Ag1ⁱⁱ	3.0193 (5)	C12—H12	0.9300
C1—N1	1.335 (4)	C13—O4	1.425 (4)
C1—C2	1.367 (5)	C13—C14	1.501 (4)
C1—H1	0.9300	C13—H13A	0.9700
C2—C3	1.382 (5)	C13—H13B	0.9700
C2—H2	0.9300	C14—C16	1.379 (4)
C3—C4	1.372 (4)	C14—C15	1.384 (4)
C3—H3	0.9300	C15—N2	1.343 (3)
C4—C5	1.386 (4)	C15—H15	0.9300
C4—C6	1.512 (4)	C16—C17	1.393 (4)
C5—N1	1.341 (4)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.375 (5)
C6—O3	1.411 (4)	C17—H17	0.9300
C6—H6A	0.9700	C18—N2	1.337 (4)
C6—H6B	0.9700	C18—H18	0.9300
C7—C12	1.377 (5)	C19—O2	1.228 (4)
C7—O3	1.382 (3)	C19—O1	1.250 (4)
C7—C8	1.384 (4)	C19—C20	1.502 (4)
C8—C9	1.393 (4)	C20—C20ⁱⁱⁱ	1.309 (6)
C8—H8	0.9300	C20—H20	0.9300
C9—C10	1.366 (4)	N2—Ag1^iv	2.202 (2)
C9—H9	0.9300	O1W—H1A	0.85 (6)
C10—C11	1.386 (4)	O1W—H1B	0.85 (5)

N2ⁱ—Ag1—N1	153.76 (10)	C10—C11—H11	119.6
N2ⁱ—Ag1—O2	116.46 (9)	C7—C12—C11	118.9 (3)
N1—Ag1—O2	89.76 (9)	C7—C12—H12	120.5
N2ⁱ—Ag1—Ag1ⁱⁱ	106.01 (7)	C11—C12—H12	120.5
N1—Ag1—Ag1ⁱⁱ	85.94 (7)	O4—C13—C14	108.2 (2)
O2—Ag1—Ag1ⁱⁱ	63.49 (6)	O4—C13—H13A	110.1
N1—C1—C2	122.8 (3)	C14—C13—H13A	110.1
N1—C1—H1	118.6	O4—C13—H13B	110.1
C2—C1—H1	118.6	C14—C13—H13B	110.1
C1—C2—C3	119.0 (3)	H13A—C13—H13B	108.4
C1—C2—H2	120.5	C16—C14—C15	118.0 (3)
C3—C2—H2	120.5	C16—C14—C13	123.5 (3)
C4—C3—C2	119.5 (3)	C15—C14—C13	118.4 (3)
C4—C3—H3	120.2	N2—C15—C14	123.4 (3)
C2—C3—H3	120.2	N2—C15—H15	118.3
C3—C4—C5	117.7 (3)	C14—C15—H15	118.3
C3—C4—C6	123.3 (3)	C14—C16—C17	119.1 (3)
C5—C4—C6	119.0 (3)	C14—C16—H16	120.5
N1—C5—C4	123.3 (3)	C17—C16—H16	120.5
N1—C5—H5	118.4	C18—C17—C16	119.0 (3)
C4—C5—H5	118.4	C18—C17—H17	120.5
O3—C6—C4	107.4 (2)	C16—C17—H17	120.5
O3—C6—H6A	110.2	N2—C18—C17	122.6 (3)
C4—C6—H6A	110.2	N2—C18—H18	118.7
O3—C6—H6B	110.2	C17—C18—H18	118.7
C4—C6—H6B	110.2	O2—C19—O1	124.1 (3)
H6A—C6—H6B	108.5	O2—C19—C20	118.8 (3)
C12—C7—O3	125.2 (3)	O1—C19—C20	117.1 (3)
C12—C7—C8	120.7 (3)	C20ⁱⁱⁱ—C20—C19	124.6 (4)
O3—C7—C8	114.1 (3)	C20ⁱⁱⁱ—C20—H20	117.7
C7—C8—C9	119.7 (3)	C19—C20—H20	117.7
C7—C8—H8	120.1	C1—N1—C5	117.7 (3)
C9—C8—H8	120.1	C1—N1—Ag1	118.8 (2)
C10—C9—C8	120.0 (3)	C5—N1—Ag1	123.5 (2)
C10—C9—H9	120.0	C18—N2—C15	117.9 (3)
C8—C9—H9	120.0	C18—N2—Ag1^iv	122.60 (19)
C9—C10—C11	119.9 (3)	C15—N2—Ag1^iv	119.5 (2)
C9—C10—O4	124.3 (3)	C19—O2—Ag1	99.6 (2)
C11—C10—O4	115.8 (3)	C7—O3—C6	117.5 (2)
C12—C11—C10	120.8 (3)	C10—O4—C13	115.5 (2)
C12—C11—H11	119.6	H1A—O1W—H1B	106 (6)

N1—C1—C2—C3	2.4 (6)	O1—C19—C20—C20ⁱⁱⁱ	172.3 (4)
C1—C2—C3—C4	−0.9 (6)	C2—C1—N1—C5	−1.6 (5)
C2—C3—C4—C5	−1.3 (5)	C2—C1—N1—Ag1	−179.4 (3)
C2—C3—C4—C6	178.6 (3)	C4—C5—N1—C1	−0.8 (5)
C3—C4—C5—N1	2.2 (5)	C4—C5—N1—Ag1	176.9 (2)
C6—C4—C5—N1	−177.7 (3)	N2ⁱ—Ag1—N1—C1	−109.7 (3)
C3—C4—C6—O3	1.5 (4)	O2—Ag1—N1—C1	68.1 (3)
C5—C4—C6—O3	−178.6 (3)	Ag1ⁱⁱ—Ag1—N1—C1	131.5 (3)
C12—C7—C8—C9	1.5 (5)	N2ⁱ—Ag1—N1—C5	72.7 (3)
O3—C7—C8—C9	−179.3 (3)	O2—Ag1—N1—C5	−109.5 (2)
C7—C8—C9—C10	−0.8 (5)	Ag1ⁱⁱ—Ag1—N1—C5	−46.1 (2)
C8—C9—C10—C11	−0.7 (5)	C17—C18—N2—C15	0.8 (5)
C8—C9—C10—O4	179.9 (3)	C17—C18—N2—Ag1^iv	−178.9 (3)
C9—C10—C11—C12	1.5 (5)	C14—C15—N2—C18	−0.9 (5)
O4—C10—C11—C12	−179.0 (3)	C14—C15—N2—Ag1^iv	178.7 (2)
O3—C7—C12—C11	−179.8 (3)	O1—C19—O2—Ag1	−7.9 (4)
C8—C7—C12—C11	−0.7 (5)	C20—C19—O2—Ag1	173.8 (2)
C10—C11—C12—C7	−0.8 (5)	N2ⁱ—Ag1—O2—C19	65.7 (2)
O4—C13—C14—C16	−30.1 (4)	N1—Ag1—O2—C19	−113.2 (2)
O4—C13—C14—C15	152.9 (3)	Ag1ⁱⁱ—Ag1—O2—C19	161.2 (2)
C16—C14—C15—N2	0.1 (5)	C12—C7—O3—C6	4.0 (5)
C13—C14—C15—N2	177.3 (3)	C8—C7—O3—C6	−175.2 (3)
C15—C14—C16—C17	0.9 (5)	C4—C6—O3—C7	−178.9 (3)
C13—C14—C16—C17	−176.2 (3)	C9—C10—O4—C13	−1.1 (5)
C14—C16—C17—C18	−1.0 (6)	C11—C10—O4—C13	179.4 (3)
C16—C17—C18—N2	0.2 (6)	C14—C13—O4—C10	−179.0 (3)
O2—C19—C20—C20ⁱⁱⁱ	−9.4 (6)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1B···O1	0.85 (5)	2.23 (5)	2.941 (6)	141 (7)
O1W—H1A···O1^v	0.85 (6)	2.07 (3)	2.888 (5)	162 (8)

Symmetry code: (v) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Ag(C₁₈H₁₆N₂O₂)(C₄H₂O₄)_0.5]·H₂O
M_r	475.24
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.5730 (8), 9.7120 (9), 12.0990 (11)
α, β, γ (°)	88.845 (2), 71.867 (1), 77.047 (2)
V (Å³)	931.65 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.12
Crystal size (mm)	0.42 × 0.36 × 0.35

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.632, 0.676
No. of measured, independent and observed [I > 2σ(I)] reflections	5611, 4127, 3629
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.672

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.107, 1.09
No. of reflections	4127
No. of parameters	259
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.17, −0.57

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990).