catena-Poly[[silver(I)-μ-1,2-bis­(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)ethane-κ2N:N′] perchlorate hemihydrate]

Yeh, C.-W.; Huang, F.-C.; Lin, S.-C.; Jong, A.; Suen, M.-C.

doi:10.1107/S1600536812016406

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages m637-m638

doi:10.1107/S1600536812016406

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catena-Poly[[silver(I)-μ-1,2-bis(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)ethane-κ²N:N′] perchlorate hemihydrate]

Chun-Wei Yeh,^a Fu-Chang Huang,^b Shui-Chuan Lin,^c Ay Jong ^d and Maw-Cherng Suen ^e ^*

^aDepartment of Chemistry, Chung-Yuan Christian University, Jhongli 32023, Taiwan, ^bDepartment of Civil and Environmental Engineering, Nanya Institute of Technology, Jhongli 32091, Taiwan, ^cDepartment of Chemical and Material Engineering, Nanya Institute of Technology, Jhongli 32091, Taiwan, ^dDepartment of Polymer Materials, Vanung University, Jhongli 32061, Taiwan, and ^eDepartment of Materials and Fibers, Nanya Institute of Technology, Jhongli 32091, Taiwan
^*Correspondence e-mail: sun@tiit.edu.tw

(Received 29 March 2012; accepted 16 April 2012; online 21 April 2012)

In the title coordination polymer, {[Ag(C₁₂H₂₀N₂O₂)]ClO₄·0.5H₂O}_n, the Ag^I cation is coordinated by two N atoms from two 1,2-bis(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)ethane (L) ligands in a nearly linear geometry [N—Ag—N = 171.07 (8)°]. The L ligand bridges adjacent Ag⁺ cations, forming a polymeric chain running along the c axis. The lattice water molecule is situated on a twofold rotation axis, and links to the perchlorate anion via an O—H⋯O hydrogen bond. The long Ag⋯O separation of 3.200 (4) Å indicates a weak interaction between the perchlorate anion and the Ag^I cation. Weak C—H⋯O hydrogen bonding occurs between the chain and the lattice water molecule and between the chain and perchlorate anions. Both five-membered rings of the L ligand display envelope conformations; in one five-membered ring, the flap C atom is disordered on opposite sides of the ring with occupancies of 0.65 and 0.35.

Related literature

For background to coordination polymers with organic ligands, see: Kitagawa et al. (2004 ); Chiang et al. (2008 ); Yeh et al. (2008 , 2009 ); Hsu et al. (2009 ). For related structures, see: Wang et al. (2008 , 2011 ); Suen et al. (2011 ).

Experimental

Crystal data

[Ag(C₁₂H₂₀N₂O₂)]ClO₄·0.5H₂O
M_r = 881.26
Monoclinic, C 2/c
a = 25.3322 (19) Å
b = 11.2100 (9) Å
c = 12.3721 (9) Å
β = 97.917 (1)°
V = 3479.9 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.34 mm⁻¹
T = 297 K
0.5 × 0.4 × 0.4 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.753, T_max = 1.000
9583 measured reflections
3424 independent reflections
2914 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.090
S = 1.23
3424 reflections
217 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7C⋯O3	0.87 (5)	2.06 (5)	2.926 (4)	175 (4)
C4—H4C⋯O7ⁱ	0.97	2.47	3.379 (4)	156
C5—H5B⋯O5ⁱⁱ	0.97	2.39	3.289 (5)	153
Symmetry codes: (i) -x, -y, -z+1; (ii) $[x, -y, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2010 ); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2010 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812016406/xu5506sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812016406/xu5506Isup2.hkl

checkCIF report

Comment top

The synthesis of metal coordination polymers has been a subject of intense research due to their interesting structural chemistry and potential applications in gas storage, separation, catalysis, magnetism, luminescence, and drug delivery (Kitagawa et al., 2004). Roles of anion, solvent and ligand comformations in self-assembly of coordination complexes containing polydentate nitrogen ligands are very intersting (Chiang et al., 2008; Yeh et al., 2008; Hsu et al., 2009; Yeh et al., 2009). The d¹⁰ metal complexes containing 1,4-bis(4,5-dihydro-2-oxazolyl)benzene ligands (L') have been reported, which show various two-dimensional networks (Wang et al., 2008, Wang et al., 2011 and Suen et al., 2011). The Ag⁺ cations are coordinated with two N atoms from two 1,2-bis(4,4-dimethyl-4,5-dihydrooxazol-2-yl)ethane (L) ligands (Fig. 1). The Ag···Ag distance separated by the bridging L ligands is 6.685 (1) Å, while the bridging L ligand adopts gauche conformation with C3—C4—C5—C6 trosion angle 67.43 (35) °. The one-dimensional polymeric chains are interlinking through Ag···O interactions [3.045 (1) and 3.199 (4) Å] and O—H···O hydrogen bonds between the Ag⁺ cations, latice water molecules and ClO₄^- anions in the crystal structure (Fig. 2, Tab.1). The C2 atom of the the dihydrooxazol-2-yl group is disordered over two sites with occupancy factors of 0.65 and 0.35.

Related literature top

For background to coordination polymers with organic ligands, see: Kitagawa et al. (2004); Chiang et al. (2008); Yeh et al. (2008, 2009); Hsu et al. (2009). For related structures, see: Wang et al. (2008, 2011); Suen et al. (2011).

Experimental top

An aqueous solution (5.0 ml) of AgClO₄ (1.0 mmol) was layered carefully over a methanolic solution (5.0 ml) of 1,2-bis(4,4-dimethyl-4,5-dihydrooxazol-2-yl)ethane (1.0 mmol) in a tube. Colourless crystals were obtained after several weeks. These were washed with methanol and collected in 68.2% yield.

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A portion of the one-dimensional chain. Ellipsoids are drawn at 30% probability level, and all the H atoms of L are omitted for clairty. Symmetry codes: (i) x,-y,z + 1/2; (ii) x,-y,z - 1/2.
	Fig. 2. The packing diagram shows the Ag···O interactions and O—H···O hydrogen bonds among the one-dimensional chains.

catena-Poly[[silver(I)-µ-1,2-bis(4,4-dimethyl-4,5-dihydro- 1,3-oxazol-2-yl)ethane-κ²N:N'] perchlorate hemihydrate] top

Crystal data top

[Ag(C₁₂H₂₀N₂O₂)]ClO₄·0.5H₂O	F(000) = 1784
M_r = 881.26	D_x = 1.682 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3424 reflections
a = 25.3322 (19) Å	θ = 1.6–26.0°
b = 11.2100 (9) Å	µ = 1.34 mm⁻¹
c = 12.3721 (9) Å	T = 297 K
β = 97.917 (1)°	Block, colourless
V = 3479.9 (5) Å³	0.5 × 0.4 × 0.4 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3424 independent reflections
Radiation source: fine-focus sealed tube	2914 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −31→29
T_min = 0.753, T_max = 1.000	k = −8→13
9583 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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.23	w = 1/[σ²(F_o²) + (0.050P)²] where P = (F_o² + 2F_c²)/3
3424 reflections	(Δ/σ)_max = 0.001
217 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

[Ag(C₁₂H₂₀N₂O₂)]ClO₄·0.5H₂O	V = 3479.9 (5) Å³
M_r = 881.26	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 25.3322 (19) Å	µ = 1.34 mm⁻¹
b = 11.2100 (9) Å	T = 297 K
c = 12.3721 (9) Å	0.5 × 0.4 × 0.4 mm
β = 97.917 (1)°

Data collection top

Bruker APEXII CCD diffractometer	3424 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2914 reflections with I > 2σ(I)
T_min = 0.753, T_max = 1.000	R_int = 0.019
9583 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.23	Δρ_max = 0.49 e Å⁻³
3424 reflections	Δρ_min = −0.41 e Å⁻³
217 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	Occ. (<1)
Ag	0.113477 (9)	−0.11300 (2)	0.375689 (18)	0.05407 (11)
Cl	0.10569 (3)	0.21893 (7)	0.56478 (6)	0.0582 (2)
O1	0.15659 (9)	0.1990 (2)	0.2086 (2)	0.0816 (8)
O2	0.05890 (9)	0.35885 (18)	0.09898 (16)	0.0569 (5)
O3	0.05412 (12)	0.2480 (4)	0.5918 (3)	0.1148 (11)
O4	0.14340 (13)	0.2630 (3)	0.6480 (3)	0.1168 (11)
O5	0.11311 (18)	0.0949 (3)	0.5528 (3)	0.1163 (13)
O6	0.11177 (17)	0.2774 (3)	0.4667 (2)	0.1184 (12)
O7	0.0000	0.1184 (3)	0.7500	0.0834 (11)
N1	0.14851 (8)	0.0336 (2)	0.30542 (17)	0.0438 (5)
N2	0.08939 (8)	0.26102 (19)	−0.03635 (17)	0.0431 (5)
C1	0.20723 (11)	0.0540 (3)	0.3142 (2)	0.0542 (7)
C2	0.2107 (4)	0.1392 (8)	0.2200 (10)	0.075 (3)	0.65
H2B	0.2392	0.1965	0.2375	0.089*	0.65
H2C	0.2158	0.0966	0.1540	0.089*	0.65
C2'	0.2083 (9)	0.1825 (15)	0.2631 (19)	0.094 (7)	0.35
H2'A	0.2168	0.2422	0.3195	0.113*	0.35
H2'B	0.2343	0.1870	0.2126	0.113*	0.35
C3	0.12504 (12)	0.1175 (2)	0.2487 (2)	0.0503 (7)
C4	0.06708 (11)	0.1381 (3)	0.2236 (2)	0.0531 (7)
H4B	0.0582	0.2111	0.2591	0.064*
H4C	0.0485	0.0731	0.2537	0.064*
C5	0.04721 (11)	0.1478 (3)	0.1008 (2)	0.0522 (7)
H5B	0.0586	0.0777	0.0644	0.063*
H5C	0.0086	0.1487	0.0901	0.063*
C6	0.06680 (10)	0.2559 (2)	0.0495 (2)	0.0445 (6)
C7	0.08686 (15)	0.4491 (3)	0.0448 (2)	0.0649 (8)
H7A	0.1194	0.4730	0.0903	0.078*
H7B	0.0646	0.5190	0.0282	0.078*
C8	0.09930 (11)	0.3892 (2)	−0.0602 (2)	0.0469 (6)
C9	0.22808 (15)	0.0913 (4)	0.4296 (3)	0.0954 (14)
H9A	0.2305	0.0226	0.4764	0.143*
H9B	0.2042	0.1485	0.4544	0.143*
H9C	0.2627	0.1264	0.4313	0.143*
C10	0.23499 (15)	−0.0574 (4)	0.2842 (4)	0.0904 (12)
H10A	0.2245	−0.1234	0.3259	0.136*
H10B	0.2729	−0.0466	0.2998	0.136*
H10C	0.2254	−0.0734	0.2078	0.136*
C11	0.06137 (15)	0.4279 (3)	−0.1592 (3)	0.0712 (9)
H11A	0.0701	0.3873	−0.2227	0.107*
H11B	0.0644	0.5125	−0.1691	0.107*
H11C	0.0255	0.4086	−0.1487	0.107*
C12	0.15668 (16)	0.4067 (4)	−0.0786 (4)	0.0841 (12)
H12A	0.1800	0.3805	−0.0153	0.126*
H12B	0.1629	0.4896	−0.0914	0.126*
H12C	0.1635	0.3610	−0.1409	0.126*
H7C	0.0141 (19)	0.158 (4)	0.701 (4)	0.110 (16)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag	0.05656 (17)	0.04575 (16)	0.06076 (17)	−0.00549 (9)	0.01119 (11)	0.01769 (9)
Cl	0.0756 (5)	0.0481 (4)	0.0535 (4)	−0.0027 (3)	0.0185 (3)	−0.0029 (3)
O1	0.0547 (13)	0.0750 (16)	0.1129 (19)	−0.0111 (11)	0.0034 (12)	0.0533 (15)
O2	0.0834 (14)	0.0417 (11)	0.0493 (11)	0.0071 (10)	0.0223 (10)	−0.0064 (9)
O3	0.082 (2)	0.141 (3)	0.129 (2)	−0.0065 (18)	0.0404 (18)	−0.020 (2)
O4	0.104 (2)	0.107 (3)	0.127 (2)	0.0042 (18)	−0.0311 (19)	−0.028 (2)
O5	0.199 (4)	0.0521 (16)	0.111 (2)	−0.0091 (18)	0.066 (3)	−0.0039 (15)
O6	0.202 (4)	0.083 (2)	0.0810 (17)	0.033 (2)	0.059 (2)	0.0225 (16)
O7	0.095 (3)	0.059 (2)	0.097 (3)	0.000	0.017 (2)	0.000
N1	0.0465 (11)	0.0394 (12)	0.0454 (11)	−0.0039 (9)	0.0063 (9)	0.0062 (10)
N2	0.0463 (12)	0.0379 (11)	0.0450 (11)	0.0029 (9)	0.0057 (9)	−0.0084 (9)
C1	0.0448 (15)	0.0487 (16)	0.0687 (18)	−0.0047 (13)	0.0063 (13)	0.0079 (14)
C2	0.044 (3)	0.069 (6)	0.111 (7)	−0.010 (4)	0.014 (4)	0.024 (4)
C2'	0.071 (9)	0.056 (10)	0.15 (2)	−0.015 (8)	−0.017 (12)	0.047 (10)
C3	0.0490 (15)	0.0481 (17)	0.0546 (16)	−0.0082 (12)	0.0095 (12)	0.0119 (13)
C4	0.0485 (15)	0.0534 (17)	0.0589 (17)	0.0008 (13)	0.0123 (12)	0.0124 (14)
C5	0.0514 (15)	0.0446 (15)	0.0602 (17)	0.0014 (12)	0.0066 (12)	0.0046 (13)
C6	0.0457 (14)	0.0398 (14)	0.0465 (14)	0.0072 (11)	0.0009 (11)	−0.0027 (12)
C7	0.102 (3)	0.0403 (16)	0.0546 (17)	−0.0028 (16)	0.0193 (16)	−0.0061 (14)
C8	0.0525 (15)	0.0429 (15)	0.0454 (14)	−0.0048 (11)	0.0074 (12)	−0.0066 (11)
C9	0.058 (2)	0.124 (4)	0.098 (3)	0.002 (2)	−0.0095 (19)	−0.042 (3)
C10	0.062 (2)	0.099 (3)	0.112 (3)	0.006 (2)	0.017 (2)	−0.029 (3)
C11	0.096 (3)	0.058 (2)	0.0557 (18)	0.0048 (19)	−0.0021 (17)	0.0067 (16)
C12	0.066 (2)	0.084 (3)	0.105 (3)	−0.0240 (19)	0.023 (2)	−0.016 (2)

Geometric parameters (Å, º) top

Ag—N1	2.111 (2)	C3—C4	1.476 (4)
Ag—N2ⁱ	2.120 (2)	C4—C5	1.537 (4)
Cl—O4	1.394 (3)	C4—H4B	0.9700
Cl—O6	1.406 (3)	C4—H4C	0.9700
Cl—O5	1.413 (3)	C5—C6	1.484 (4)
Cl—O3	1.430 (3)	C5—H5B	0.9700
O1—C3	1.352 (3)	C5—H5C	0.9700
O1—C2'	1.40 (2)	C7—C8	1.533 (4)
O1—C2	1.514 (11)	C7—H7A	0.9700
O2—C6	1.335 (3)	C7—H7B	0.9700
O2—C7	1.451 (4)	C8—C11	1.513 (4)
O7—H7C	0.87 (4)	C8—C12	1.515 (5)
N1—C3	1.271 (4)	C9—H9A	0.9600
N1—C1	1.494 (3)	C9—H9B	0.9600
N2—C6	1.275 (3)	C9—H9C	0.9600
N2—C8	1.495 (3)	C10—H10A	0.9600
N2—Agⁱⁱ	2.120 (2)	C10—H10B	0.9600
C1—C10	1.505 (5)	C10—H10C	0.9600
C1—C9	1.512 (5)	C11—H11A	0.9600
C1—C2	1.518 (12)	C11—H11B	0.9600
C1—C2'	1.574 (19)	C11—H11C	0.9600
C2—H2B	0.9700	C12—H12A	0.9600
C2—H2C	0.9700	C12—H12B	0.9600
C2'—H2'A	0.9700	C12—H12C	0.9600
C2'—H2'B	0.9700

N1—Ag—N2ⁱ	171.07 (8)	H4B—C4—H4C	107.7
O4—Cl—O6	109.1 (3)	C6—C5—C4	113.4 (2)
O4—Cl—O5	109.7 (2)	C6—C5—H5B	108.9
O6—Cl—O5	109.7 (2)	C4—C5—H5B	108.9
O4—Cl—O3	107.6 (2)	C6—C5—H5C	108.9
O6—Cl—O3	107.9 (2)	C4—C5—H5C	108.9
O5—Cl—O3	112.8 (2)	H5B—C5—H5C	107.7
C3—O1—C2'	107.2 (9)	N2—C6—O2	117.1 (2)
C3—O1—C2	103.9 (4)	N2—C6—C5	127.5 (2)
C2'—O1—C2	28.7 (9)	O2—C6—C5	115.4 (2)
C6—O2—C7	106.1 (2)	O2—C7—C8	104.8 (2)
C3—N1—C1	108.2 (2)	O2—C7—H7A	110.8
C3—N1—Ag	127.74 (19)	C8—C7—H7A	110.8
C1—N1—Ag	124.10 (17)	O2—C7—H7B	110.8
C6—N2—C8	108.3 (2)	C8—C7—H7B	110.8
C6—N2—Agⁱⁱ	125.88 (19)	H7A—C7—H7B	108.9
C8—N2—Agⁱⁱ	125.67 (16)	N2—C8—C11	109.3 (2)
N1—C1—C10	110.4 (3)	N2—C8—C12	110.2 (3)
N1—C1—C9	109.0 (3)	C11—C8—C12	110.9 (3)
C10—C1—C9	110.3 (3)	N2—C8—C7	101.2 (2)
N1—C1—C2	101.7 (4)	C11—C8—C7	112.3 (3)
C10—C1—C2	104.8 (4)	C12—C8—C7	112.6 (3)
C9—C1—C2	120.1 (5)	C1—C9—H9A	109.5
N1—C1—C2'	100.6 (8)	C1—C9—H9B	109.5
C10—C1—C2'	128.8 (9)	H9A—C9—H9B	109.5
C9—C1—C2'	95.9 (9)	C1—C9—H9C	109.5
C2—C1—C2'	27.2 (9)	H9A—C9—H9C	109.5
O1—C2—C1	101.7 (6)	H9B—C9—H9C	109.5
O1—C2—H2B	111.4	C1—C10—H10A	109.5
C1—C2—H2B	111.4	C1—C10—H10B	109.5
O1—C2—H2C	111.4	H10A—C10—H10B	109.5
C1—C2—H2C	111.4	C1—C10—H10C	109.5
H2B—C2—H2C	109.3	H10A—C10—H10C	109.5
O1—C2'—C1	104.3 (12)	H10B—C10—H10C	109.5
O1—C2'—H2'A	110.9	C8—C11—H11A	109.5
C1—C2'—H2'A	110.9	C8—C11—H11B	109.5
O1—C2'—H2'B	110.9	H11A—C11—H11B	109.5
C1—C2'—H2'B	110.9	C8—C11—H11C	109.5
H2'A—C2'—H2'B	108.9	H11A—C11—H11C	109.5
N1—C3—O1	116.6 (3)	H11B—C11—H11C	109.5
N1—C3—C4	127.4 (3)	C8—C12—H12A	109.5
O1—C3—C4	116.0 (2)	C8—C12—H12B	109.5
C3—C4—C5	113.6 (2)	H12A—C12—H12B	109.5
C3—C4—H4B	108.9	C8—C12—H12C	109.5
C5—C4—H4B	108.9	H12A—C12—H12C	109.5
C3—C4—H4C	108.9	H12B—C12—H12C	109.5
C5—C4—H4C	108.9

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
O7—H7C···O3	0.87 (5)	2.06 (5)	2.926 (4)	175 (4)
C4—H4C···O7ⁱⁱⁱ	0.97	2.47	3.379 (4)	156
C5—H5B···O5ⁱⁱ	0.97	2.39	3.289 (5)	153

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

Experimental details

Crystal data
Chemical formula	[Ag(C₁₂H₂₀N₂O₂)]ClO₄·0.5H₂O
M_r	881.26
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	297
a, b, c (Å)	25.3322 (19), 11.2100 (9), 12.3721 (9)
β (°)	97.917 (1)
V (Å³)	3479.9 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.34
Crystal size (mm)	0.5 × 0.4 × 0.4

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.753, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9583, 3424, 2914
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.090, 1.23
No. of reflections	3424
No. of parameters	217
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.41

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7C···O3	0.87 (5)	2.06 (5)	2.926 (4)	175 (4)
C4—H4C···O7ⁱ	0.97	2.47	3.379 (4)	156
C5—H5B···O5ⁱⁱ	0.97	2.39	3.289 (5)	153

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

Acknowledgements

We are grateful to the National Science Council of the Republic of China and the Nanya Institute of Technology for support.

References

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