Poly[[μ2-acetato-aquadi-μ3-isonicotinato-holmium(III)silver(I)] perchlorate]

Feng, S.

doi:10.1107/S1600536809046601

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1619

doi:10.1107/S1600536809046601

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Poly[[μ₂-acetato-aquadi-μ₃-isonicotinato-holmium(III)silver(I)] perchlorate]

Sun Feng ^a ^*

^aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510631, People's Republic of China
^*Correspondence e-mail: fengsun1974@yahoo.com.cn

(Received 20 October 2009; accepted 5 November 2009; online 21 November 2009)

In the title three-dimensional heterometallic complex, {[AgHo(C₆H₄NO₂)₂(C₂H₃O₂)(H₂O)]ClO₄}_n, the Ho^III ion is eight-coordinated by four O atoms from four different isonicotinate ligands, three O atoms from two different acetate ligands and one O atom of a water molecule. The two-coordinate Ag^I ion is bonded to two N atoms from two different isonicotinate anions. These metal coordination units are connected by bridging isonicotinate and acetate ligands, generating a three-dimensional network. The coordinated water molecules link the carboxylate group of the acetate ligand and the nitrate ligand by O—H⋯O hydrogen bonding. The crystal structure is further stabilized by hydrogen bonds. The perchlorate ion is disordered over two sites with site-occupancy factors 0.539 (12) and 0.461 (12), while the methyl group of the acetate ligand is disordered over two sites with site-occupancy factors 0.51 (4) and 0.49 (4).

Related literature

For the applications of lanthanide–transition metal heterometallic complexes in ion exchange, magnetism, bimetallic catalysis and as luminescent probes, see: Cheng et al. (2006 ); Kuang et al. (2007 ); Peng et al. (2008 ); Zhu et al. (2009 ).

Experimental

Crystal data

[AgHo(C₆H₄NO₂)₂(C₂H₃O₂)(H₂O)]ClO₄
M_r = 693.51
Monoclinic, P 2₁ /c
a = 16.2158 (10) Å
b = 14.9024 (9) Å
c = 7.9068 (5) Å
β = 91.826 (1)°
V = 1909.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 5.34 mm⁻¹
T = 296 K
0.20 × 0.18 × 0.15 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.357, T_max = 0.449
9735 measured reflections
3439 independent reflections
3085 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.054
S = 1.04
3439 reflections
320 parameters
158 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.71 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O4ⁱ	0.82 (4)	2.19 (3)	2.898 (4)	145 (4)
O1W—H2W⋯O6ⁱⁱ	0.81 (4)	1.99 (4)	2.787 (4)	168 (5)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809046601/pv2224sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809046601/pv2224Isup2.hkl

checkCIF report

Comment top

In the past few years, lanthanide-transition metal heterometallic complexs with bridging multifunctionnal organic ligands are of increasing interest, not only because of their impressive topological structures, but also due to their versatile applications in ion exchange, magnetism, bimetallic catalysis and luminescent probe(Cheng et al., 2006; Kuang et al., 2007; Peng et al., 2008; Zhu et al., 2009). As an extension of this research, the structure of the title compound, a new heterometallic coordination polymer, (I), has been determined which is presented in this artcle.

The asymmetric unite of the title compound (Fig. 1), contains one of each of the Ho^III and Ag^I ions, two halves of acetate ligand, two isonicotinate ligands, and one coordinated water molecule. The Ho^III ion is eight-coordinated by four O atoms from four different isonicotinate ligands, and three O atoms from two different acetate ligands, and one O atom of water molecule; the Ho center can be described as adopting a bicapped trigonal prism coordination geometry. The two-coordinate Ag^I ion is bonded to two N atoms from two different isonicotinate anions. Thus the Ag^I ion is in a somewhat liner coformation with N1—Ag1—N2 angle 165.55 (17) °. These metal coordination units are connected by bridging isonicotinate and acetate ligands, generating a three-dimensional network (Fig. 2). The coordinated water molecules link the carboxylate group and acetate ligand by O—H···O hydrogen bonding (Table 1). The crystal structure is further stabilized by hydrogen bonds.

Related literature top

For the applications of lanthanide–transition metal heterometallic complexes in ion exchange, magnetism, bimetallic catalysis and as luminescent probes, see: Cheng et al. (2006); Kuang et al. (2007); Peng et al. (2008); Zhu et al. (2009).

Experimental top

A mixture of AgNO₃(0.057 g, 0.33 mmol), Ho₂O₃(0.116 g, 0.33 mmol), isonicotinic acid(0.164 g, 1.33 mmol), CH₃COONa(0.057 g, 0.7 mmol), H₂O(7 ml), and HClO₄(0.257 mmol)(pH 2) was sealed in a 20 ml Teflon-lined reaction vessel at 443 K for 6 days then slowly cooled to room temperature. The product was collected by filtration, washed with water and air-dried. Colorless block crystals suitable for X-ray analysis were obtained.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure showing the atomic-numbering scheme and displacement ellipsoids drawn at the 30% probability level. Symmetry codes: (A) 1 - x, 1 - y, -z; (B) x, 0.5 - y, 1/2 + z; (C) -x, 1/2 + y, 0.5 - z; (D) 1 + x, 0.5 - y, -1/2 + z.
	Fig. 2. A view of the three-dimensional structure of the title compound.

Poly[[µ₂-acetato-aquadi-µ₃-isonicotinato-holmium(III)silver(I)] perchlorate] top

Crystal data top

[AgHo(C₆H₄NO₂)₂(C₂H₃O₂)(H₂O)]ClO₄	F(000) = 1320
M_r = 693.51	D_x = 2.412 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5514 reflections
a = 16.2158 (10) Å	θ = 2.5–27.8°
b = 14.9024 (9) Å	µ = 5.34 mm⁻¹
c = 7.9068 (5) Å	T = 296 K
β = 91.826 (1)°	Block, colorless
V = 1909.7 (2) Å³	0.20 × 0.18 × 0.15 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	3439 independent reflections
Radiation source: fine-focus sealed tube	3085 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scan	θ_max = 25.2°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→19
T_min = 0.357, T_max = 0.449	k = −17→17
9735 measured reflections	l = −7→9

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.054	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0229P)² + 2.5125P] where P = (F_o² + 2F_c²)/3
3439 reflections	(Δ/σ)_max = 0.001
320 parameters	Δρ_max = 0.64 e Å⁻³
158 restraints	Δρ_min = −0.71 e Å⁻³

Crystal data top

[AgHo(C₆H₄NO₂)₂(C₂H₃O₂)(H₂O)]ClO₄	V = 1909.7 (2) Å³
M_r = 693.51	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.2158 (10) Å	µ = 5.34 mm⁻¹
b = 14.9024 (9) Å	T = 296 K
c = 7.9068 (5) Å	0.20 × 0.18 × 0.15 mm
β = 91.826 (1)°

Data collection top

Bruker APEXII area-detector diffractometer	3439 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3085 reflections with I > 2σ(I)
T_min = 0.357, T_max = 0.449	R_int = 0.027
9735 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	158 restraints
wR(F²) = 0.054	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.64 e Å⁻³
3439 reflections	Δρ_min = −0.71 e Å⁻³
320 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)
Ho1	0.454984 (11)	0.383812 (12)	0.04996 (2)	0.01844 (7)
Ag1	−0.02677 (3)	0.24033 (4)	0.10033 (7)	0.06287 (16)
C1	−0.3677 (3)	0.0808 (3)	0.3622 (6)	0.0313 (10)
C2	−0.2892 (3)	0.1236 (3)	0.3041 (6)	0.0289 (10)
C3	−0.2191 (3)	0.0720 (3)	0.2964 (7)	0.0410 (12)
H10	−0.2199	0.0117	0.3268	0.049*
C4	−0.1474 (3)	0.1114 (4)	0.2427 (8)	0.0519 (15)
H8	−0.1002	0.0762	0.2380	0.062*
C5	−0.2111 (3)	0.2470 (3)	0.2064 (8)	0.0481 (14)
H7	−0.2086	0.3072	0.1761	0.058*
C6	−0.2852 (3)	0.2128 (3)	0.2588 (7)	0.0409 (12)
H9	−0.3315	0.2493	0.2634	0.049*
C7	0.1336 (3)	0.1719 (4)	−0.0405 (7)	0.0442 (13)
H5	0.1066	0.1176	−0.0251	0.053*
C8	0.2120 (3)	0.1707 (3)	−0.1043 (6)	0.0351 (11)
H4	0.2372	0.1166	−0.1302	0.042*
C9	0.2521 (3)	0.2510 (3)	−0.1289 (5)	0.0230 (9)
C10	0.3375 (2)	0.2510 (3)	−0.1983 (5)	0.0206 (9)
C11	0.2125 (3)	0.3295 (3)	−0.0872 (6)	0.0325 (11)
H3	0.2382	0.3846	−0.1017	0.039*
C12	0.1343 (3)	0.3254 (3)	−0.0238 (6)	0.0376 (12)
H6	0.1080	0.3787	0.0034	0.045*
N1	−0.1427 (2)	0.1969 (3)	0.1974 (6)	0.0458 (11)
N2	0.0950 (2)	0.2480 (3)	0.0001 (5)	0.0394 (10)
O1	−0.4242 (2)	0.1332 (2)	0.4072 (5)	0.0387 (9)
O2	−0.3699 (2)	−0.0029 (2)	0.3616 (4)	0.0397 (8)
O3	0.35906 (18)	0.18441 (19)	−0.2810 (4)	0.0303 (7)
O4	0.38257 (17)	0.31880 (19)	−0.1691 (4)	0.0260 (7)
O5	0.54736 (19)	0.5035 (2)	0.1583 (4)	0.0312 (7)
O6	0.5344 (2)	0.3847 (2)	0.3129 (4)	0.0352 (8)
O1W	0.4985 (2)	0.2318 (2)	0.0763 (4)	0.0353 (8)
H1W	0.478 (3)	0.197 (2)	0.143 (5)	0.053*
H2W	0.516 (3)	0.200 (3)	0.002 (4)	0.053*
C13	0.5691 (3)	0.4589 (3)	0.2876 (5)	0.0272 (10)
C14	0.6256 (13)	0.4991 (15)	0.423 (2)	0.040 (3)	0.49 (4)
H14A	0.5956	0.5074	0.5247	0.060*	0.49 (4)
H14B	0.6457	0.5560	0.3852	0.060*	0.49 (4)
H14C	0.6713	0.4594	0.4455	0.060*	0.49 (4)
C14'	0.6450 (11)	0.4886 (16)	0.388 (3)	0.040 (3)	0.51 (4)
H14D	0.6545	0.4486	0.4821	0.060*	0.51 (4)
H14E	0.6368	0.5484	0.4297	0.060*	0.51 (4)
H14F	0.6918	0.4877	0.3171	0.060*	0.51 (4)
Cl1	0.91931 (10)	0.45924 (11)	0.2560 (2)	0.0625 (4)	0.539 (12)
O7	0.8512 (8)	0.4643 (8)	0.3717 (18)	0.126 (5)	0.539 (12)
O8	0.8847 (9)	0.4462 (8)	0.0955 (12)	0.111 (5)	0.539 (12)
O9	0.9703 (9)	0.3896 (8)	0.300 (2)	0.130 (6)	0.539 (12)
O10	0.9589 (10)	0.5442 (8)	0.259 (2)	0.086 (6)	0.539 (12)
Cl1'	0.91931 (10)	0.45924 (11)	0.2560 (2)	0.0625 (4)	0.461 (12)
O7'	0.8366 (6)	0.4707 (8)	0.210 (2)	0.094 (5)	0.461 (12)
O8'	0.9624 (10)	0.4225 (10)	0.1137 (18)	0.132 (6)	0.461 (12)
O9'	0.9275 (11)	0.3943 (10)	0.3831 (18)	0.131 (7)	0.461 (12)
O10'	0.9581 (11)	0.5392 (9)	0.304 (2)	0.082 (6)	0.461 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ho1	0.01607 (11)	0.01592 (11)	0.02369 (12)	−0.00070 (7)	0.00617 (7)	−0.00010 (7)
Ag1	0.0259 (2)	0.0859 (4)	0.0783 (3)	−0.0142 (2)	0.0260 (2)	0.0008 (3)
C1	0.027 (2)	0.023 (2)	0.044 (3)	−0.0049 (19)	0.016 (2)	−0.004 (2)
C2	0.027 (2)	0.027 (2)	0.033 (2)	−0.0057 (19)	0.0118 (19)	−0.0029 (19)
C3	0.027 (3)	0.028 (3)	0.069 (4)	0.002 (2)	0.017 (2)	0.004 (2)
C4	0.027 (3)	0.046 (4)	0.083 (4)	0.000 (2)	0.017 (3)	−0.006 (3)
C5	0.033 (3)	0.034 (3)	0.078 (4)	−0.009 (2)	0.020 (3)	0.008 (3)
C6	0.026 (3)	0.033 (3)	0.064 (4)	−0.001 (2)	0.017 (2)	0.005 (2)
C7	0.032 (3)	0.041 (3)	0.060 (3)	−0.013 (2)	0.014 (2)	0.003 (3)
C8	0.028 (3)	0.028 (3)	0.050 (3)	−0.0040 (19)	0.012 (2)	−0.001 (2)
C9	0.019 (2)	0.027 (2)	0.023 (2)	−0.0016 (17)	0.0029 (17)	−0.0019 (17)
C10	0.018 (2)	0.022 (2)	0.023 (2)	0.0006 (16)	0.0015 (17)	0.0003 (17)
C11	0.025 (2)	0.028 (3)	0.045 (3)	−0.0027 (19)	0.012 (2)	−0.002 (2)
C12	0.028 (3)	0.035 (3)	0.051 (3)	0.005 (2)	0.015 (2)	−0.001 (2)
N1	0.025 (2)	0.046 (3)	0.067 (3)	−0.0090 (19)	0.018 (2)	−0.001 (2)
N2	0.025 (2)	0.047 (3)	0.047 (3)	−0.0028 (18)	0.0136 (18)	−0.001 (2)
O1	0.0304 (18)	0.0221 (17)	0.065 (2)	−0.0017 (13)	0.0281 (17)	−0.0023 (15)
O2	0.0346 (18)	0.0219 (17)	0.064 (2)	−0.0025 (14)	0.0279 (17)	−0.0039 (15)
O3	0.0263 (17)	0.0225 (16)	0.0431 (19)	−0.0017 (13)	0.0144 (14)	−0.0104 (14)
O4	0.0185 (15)	0.0259 (16)	0.0338 (17)	−0.0060 (12)	0.0058 (12)	−0.0054 (13)
O5	0.0382 (18)	0.0269 (17)	0.0279 (16)	−0.0076 (14)	−0.0067 (14)	0.0043 (13)
O6	0.044 (2)	0.0298 (18)	0.0315 (18)	−0.0093 (15)	−0.0022 (15)	0.0102 (14)
O1W	0.049 (2)	0.0215 (16)	0.037 (2)	0.0061 (15)	0.0189 (16)	0.0013 (14)
C13	0.028 (2)	0.029 (2)	0.025 (2)	−0.0030 (19)	−0.0014 (18)	0.0027 (19)
C14	0.039 (6)	0.044 (5)	0.036 (6)	−0.003 (5)	−0.005 (5)	−0.003 (4)
C14'	0.039 (6)	0.044 (5)	0.036 (6)	−0.003 (5)	−0.005 (5)	−0.003 (4)
Cl1	0.0599 (10)	0.0510 (9)	0.0761 (11)	0.0018 (7)	−0.0046 (8)	−0.0019 (8)
O7	0.119 (9)	0.127 (8)	0.133 (9)	−0.027 (7)	0.053 (7)	−0.013 (7)
O8	0.143 (10)	0.114 (8)	0.072 (6)	−0.050 (7)	−0.042 (6)	−0.005 (6)
O9	0.142 (9)	0.098 (7)	0.148 (10)	0.072 (7)	−0.037 (7)	−0.016 (7)
O10	0.077 (8)	0.084 (9)	0.097 (9)	−0.030 (6)	0.007 (6)	−0.010 (6)
Cl1'	0.0599 (10)	0.0510 (9)	0.0761 (11)	0.0018 (7)	−0.0046 (8)	−0.0019 (8)
O7'	0.057 (6)	0.077 (7)	0.145 (10)	0.001 (5)	−0.021 (6)	0.011 (7)
O8'	0.147 (11)	0.131 (9)	0.124 (9)	0.016 (8)	0.068 (8)	−0.035 (7)
O9'	0.143 (11)	0.133 (10)	0.117 (9)	−0.011 (8)	−0.019 (8)	0.065 (8)
O10'	0.069 (9)	0.076 (9)	0.103 (9)	−0.026 (7)	0.022 (7)	−0.045 (7)

Geometric parameters (Å, º) top

Ho1—O4	2.278 (3)	C9—C11	1.380 (6)
Ho1—O2ⁱ	2.303 (3)	C9—C10	1.504 (5)
Ho1—O1ⁱⁱ	2.306 (3)	C10—O3	1.245 (5)
Ho1—O3ⁱⁱⁱ	2.318 (3)	C10—O4	1.264 (5)
Ho1—O5^iv	2.352 (3)	C11—C12	1.379 (6)
Ho1—O1W	2.380 (3)	C11—H3	0.9300
Ho1—O6	2.410 (3)	C12—N2	1.335 (6)
Ho1—O5	2.465 (3)	C12—H6	0.9300
Ag1—N1	2.152 (4)	O1—Ho1^v	2.306 (3)
Ag1—N2	2.154 (4)	O2—Ho1^vi	2.303 (3)
C1—O2	1.248 (5)	O3—Ho1^vii	2.318 (3)
C1—O1	1.264 (5)	O5—C13	1.260 (5)
C1—C2	1.509 (6)	O5—Ho1^iv	2.352 (3)
C2—C3	1.376 (6)	O6—C13	1.259 (5)
C2—C6	1.379 (7)	O1W—H1W	0.82 (4)
C3—C4	1.380 (7)	O1W—H2W	0.81 (4)
C3—H10	0.9300	C13—C14'	1.510 (9)
C4—N1	1.327 (7)	C13—C14	1.511 (9)
C4—H8	0.9300	C14—H14A	0.9600
C5—N1	1.341 (7)	C14—H14B	0.9600
C5—C6	1.380 (6)	C14—H14C	0.9600
C5—H7	0.9300	C14'—H14D	0.9600
C6—H9	0.9300	C14'—H14E	0.9600
C7—N2	1.340 (7)	C14'—H14F	0.9600
C7—C8	1.382 (6)	Cl1—O9	1.364 (8)
C7—H5	0.9300	Cl1—O8	1.385 (8)
C8—C9	1.380 (6)	Cl1—O10	1.419 (9)
C8—H4	0.9300	Cl1—O7	1.458 (8)

O4—Ho1—O2ⁱ	104.08 (12)	C2—C6—H9	120.6
O4—Ho1—O1ⁱⁱ	90.36 (11)	C5—C6—H9	120.6
O2ⁱ—Ho1—O1ⁱⁱ	139.11 (10)	N2—C7—C8	122.7 (5)
O4—Ho1—O3ⁱⁱⁱ	84.99 (11)	N2—C7—H5	118.7
O2ⁱ—Ho1—O3ⁱⁱⁱ	74.14 (10)	C8—C7—H5	118.7
O1ⁱⁱ—Ho1—O3ⁱⁱⁱ	146.11 (10)	C9—C8—C7	119.0 (4)
O4—Ho1—O5^iv	76.99 (10)	C9—C8—H4	120.5
O2ⁱ—Ho1—O5^iv	72.10 (11)	C7—C8—H4	120.5
O1ⁱⁱ—Ho1—O5^iv	74.39 (11)	C11—C9—C8	118.4 (4)
O3ⁱⁱⁱ—Ho1—O5^iv	136.13 (11)	C11—C9—C10	121.9 (4)
O4—Ho1—O1W	78.79 (12)	C8—C9—C10	119.7 (4)
O2ⁱ—Ho1—O1W	148.20 (11)	O3—C10—O4	124.2 (4)
O1ⁱⁱ—Ho1—O1W	71.57 (11)	O3—C10—C9	118.0 (3)
O3ⁱⁱⁱ—Ho1—O1W	74.60 (10)	O4—C10—C9	117.8 (3)
O5^iv—Ho1—O1W	137.66 (11)	C12—C11—C9	119.4 (4)
O4—Ho1—O6	155.03 (10)	C12—C11—H3	120.3
O2ⁱ—Ho1—O6	92.45 (12)	C9—C11—H3	120.3
O1ⁱⁱ—Ho1—O6	89.10 (12)	N2—C12—C11	122.5 (4)
O3ⁱⁱⁱ—Ho1—O6	81.64 (11)	N2—C12—H6	118.7
O5^iv—Ho1—O6	126.62 (10)	C11—C12—H6	118.7
O1W—Ho1—O6	77.37 (12)	C4—N1—C5	117.7 (4)
O4—Ho1—O5	149.88 (10)	C4—N1—Ag1	116.4 (3)
O2ⁱ—Ho1—O5	74.19 (11)	C5—N1—Ag1	125.8 (4)
O1ⁱⁱ—Ho1—O5	74.55 (11)	C12—N2—C7	118.0 (4)
O3ⁱⁱⁱ—Ho1—O5	121.89 (11)	C12—N2—Ag1	123.1 (3)
O5^iv—Ho1—O5	73.91 (11)	C7—N2—Ag1	118.9 (3)
O1W—Ho1—O5	118.90 (12)	C1—O1—Ho1^v	134.8 (3)
O6—Ho1—O5	52.72 (10)	C1—O2—Ho1^vi	138.5 (3)
O4—Ho1—C13	170.02 (11)	C10—O3—Ho1^vii	149.1 (3)
O2ⁱ—Ho1—C13	83.92 (13)	C10—O4—Ho1	139.5 (3)
O1ⁱⁱ—Ho1—C13	79.67 (13)	C13—O5—Ho1^iv	160.5 (3)
O3ⁱⁱⁱ—Ho1—C13	103.15 (12)	C13—O5—Ho1	92.9 (2)
O5^iv—Ho1—C13	100.29 (11)	Ho1^iv—O5—Ho1	106.09 (11)
O1W—Ho1—C13	97.63 (13)	C13—O6—Ho1	95.6 (3)
O6—Ho1—C13	26.34 (11)	Ho1—O1W—H1W	122 (3)
O5—Ho1—C13	26.45 (11)	Ho1—O1W—H2W	127 (3)
O4—Ho1—Ho1^iv	114.60 (7)	H1W—O1W—H2W	105 (4)
O2ⁱ—Ho1—Ho1^iv	68.77 (7)	O6—C13—O5	118.5 (4)
O1ⁱⁱ—Ho1—Ho1^iv	70.43 (7)	O6—C13—C14'	122.3 (10)
O3ⁱⁱⁱ—Ho1—Ho1^iv	141.14 (7)	O5—C13—C14'	118.3 (10)
O5^iv—Ho1—Ho1^iv	37.97 (7)	O6—C13—C14	119.9 (10)
O1W—Ho1—Ho1^iv	139.55 (8)	O5—C13—C14	120.9 (10)
O6—Ho1—Ho1^iv	88.65 (7)	C14'—C13—C14	17.2 (11)
O5—Ho1—Ho1^iv	35.94 (7)	O6—C13—Ho1	58.1 (2)
C13—Ho1—Ho1^iv	62.34 (9)	O5—C13—Ho1	60.6 (2)
N1—Ag1—N2	165.55 (17)	C14'—C13—Ho1	166.4 (11)
O2—C1—O1	126.7 (4)	C14—C13—Ho1	176.2 (10)
O2—C1—C2	116.5 (4)	C13—C14—H14A	109.5
O1—C1—C2	116.8 (4)	C13—C14—H14B	109.5
C3—C2—C6	118.8 (4)	C13—C14—H14C	109.5
C3—C2—C1	118.9 (4)	C13—C14'—H14D	109.5
C6—C2—C1	122.3 (4)	C13—C14'—H14E	109.5
C2—C3—C4	118.7 (5)	H14D—C14'—H14E	109.5
C2—C3—H10	120.6	C13—C14'—H14F	109.5
C4—C3—H10	120.6	H14D—C14'—H14F	109.5
N1—C4—C3	123.3 (5)	H14E—C14'—H14F	109.5
N1—C4—H8	118.4	O9—Cl1—O8	110.5 (7)
C3—C4—H8	118.4	O9—Cl1—O10	113.8 (8)
N1—C5—C6	122.7 (5)	O8—Cl1—O10	108.2 (8)
N1—C5—H7	118.7	O9—Cl1—O7	110.2 (8)
C6—C5—H7	118.7	O8—Cl1—O7	106.8 (7)
C2—C6—C5	118.9 (5)	O10—Cl1—O7	107.0 (7)

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x+1, −y+1/2, z−1/2; (iii) x, −y+1/2, z+1/2; (iv) −x+1, −y+1, −z; (v) x−1, −y+1/2, z+1/2; (vi) −x, y−1/2, −z+1/2; (vii) x, −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—H1W···O4ⁱⁱⁱ	0.82 (4)	2.19 (3)	2.898 (4)	145 (4)
O1W—H2W···O6^vii	0.81 (4)	1.99 (4)	2.787 (4)	168 (5)

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

Experimental details

Crystal data
Chemical formula	[AgHo(C₆H₄NO₂)₂(C₂H₃O₂)(H₂O)]ClO₄
M_r	693.51
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	16.2158 (10), 14.9024 (9), 7.9068 (5)
β (°)	91.826 (1)
V (Å³)	1909.7 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.34
Crystal size (mm)	0.20 × 0.18 × 0.15

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.357, 0.449
No. of measured, independent and observed [I > 2σ(I)] reflections	9735, 3439, 3085
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.054, 1.04
No. of reflections	3439
No. of parameters	320
No. of restraints	158
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.71

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O4ⁱ	0.82 (4)	2.19 (3)	2.898 (4)	145 (4)
O1W—H2W···O6ⁱⁱ	0.81 (4)	1.99 (4)	2.787 (4)	168 (5)

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

Acknowledgements

The author acknowledges South China Normal University for supporting this work.

References

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