catena-Poly[[tetra-μ3-isonicotinato-μ3-oxalato-μ2-oxalato-disamarium(III)disilver(I)] dihydrate]

Li, Z.; Yue, S.

doi:10.1107/S1600536809054208

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Pages m88-m89

doi:10.1107/S1600536809054208

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catena-Poly[[tetra-μ₃-isonicotinato-μ₃-oxalato-μ₂-oxalato-disamarium(III)disilver(I)] dihydrate]

Zhao-yang Li ^a and Shan-tang Yue ^a ^*

^aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China
^*Correspondence e-mail: yuesht@scnu.edu.cn

(Received 8 October 2009; accepted 16 December 2009; online 24 December 2009)

In the title compound, {[AgSm(C₆H₄NO₂)₂(C₂O₄)]·H₂O}_n, the asymmetric unit contains one Sm^III ion, one Ag^I ion, two unique isonicotinate (ina) ligands, two half oxalate (ox) ligands (one on an inversion centre, the other on a twofold axis) and one uncoordinated water molecule. The central Sm^III ion is nine-coordinated by four O-donor atoms from separate bidentate bridging ox ligands and five O-donor atoms from the two ina ligands (both bidentate) and a symmetry-related ina ligand [Sm—O = 2.389 (4)–2.791 (4) Å], giving a distorted monocapped square antiprismatic geometry. The Ag^I ion is three-coordinated in a T-shaped geometry involving two ina N-donor atoms [Ag—N = 2.181 (6) and 2.185 (5) Å] and a bridging oxalate O-donor atom [Ag—O = 2.620 (4) Å]. The three-dimensional heterometallic Sm—Ag coordination polymer, having a unique (3,4,6)-connected five-nodal net topology, is constructed from two-dimensional samarium–oxalate layers and pillared Ag(ina)₂ subunits. Intermolecular water–carboxylate O—H⋯O hydrogen-bonding interactions are also present.

Related literature

For microporous metal-organic framework (MMOF) compounds, see: Sun et al. (2006 ); Wu & Lin (2005 ); Cho et al. (2006 ). For isonicotinic acid-heterometallic compounds, see: Cai et al. (2009 ); Gu & Xue (2006 , 2007 ); Ma et al. (2009 ). For topological studies, see: Blatov et al. (2000 ); Blatov & Shevchenko (2006 ).

Experimental

Crystal data

[AgSm(C₆H₄NO₂)₂(C₂O₄)]·H₂O
M_r = 608.47
Monoclinic, C 2/c
a = 22.0484 (18) Å
b = 9.2372 (8) Å
c = 17.1137 (14) Å
β = 108.123 (1)°
V = 3312.6 (5) Å³
Z = 8
Mo Kα radiation
μ = 4.75 mm⁻¹
T = 298 K
0.30 × 0.23 × 0.18 mm

Data collection

Bruker SMART APEX CCD-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.330, T_max = 0.482
8766 measured reflections
3240 independent reflections
2789 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.097
S = 1.08
3240 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 1.43 e Å⁻³
Δρ_min = −1.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O8ⁱ	0.86	2.16	2.960 (8)	156
O1W—H2W⋯O3	0.86	2.31	2.915 (7)	128
Symmetry code: (i) $[-x+1, y, -z-{\script{1\over 2}}]$ .

Data collection: SMART (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809054208/zs2014sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809054208/zs2014Isup2.hkl

checkCIF report

Comment top

Microporous metal-organic frameworks (MMOFs) are of great current interest in view of their fascinating structural topologies and potential applications, e.g. in small molecule gas storage, separation and catalysis (Sun et al., 2006; Wu et al., 2005; Cho et al., 2006). However, most of the works have so far focused on the assembly of 3d block metals with organic ligands as linkers and many 3d-4f heterometallic MOFs have also been reported. However, the 4d-4f heterometallic compounds based on the isonicotinic acid (ina) ligand have received less attention (Gu et al., 2006; Gu et al., 2007; Ma et al., 2009; Cai et al., 2009). The preparation of 4d-4f MMOFs has certain difficulties because of the high coordination number of 4f block metals, which frequently leads to interpenetration and consequently results in a decrease of the pore size or the MMOF may even become nonporous. Therefore the selection of the organic ligands becomes a key point in the preparation of 4d-4f heterometallic MMOFs. Herein, we report the structure of the title compound {[SmAg(C₆H₄NO₂)₂(C₂O₄)].H₂O}_n (I) involving Sm^III, Ag^I and the organic nicotinate and oxalate ligands, which has a microporous structure.

In the title compound (Fig. 1), the asymmetric unit contains one Sm^III ion, one Ag^I ion, two unique isonicotinate (ina) ligands, two half oxalate (ox) ligands [one on an inversion centre (associated with O5 and O6), the other on a two-fold axis (associated with O7 and O8)] and one uncoordinated water molecule of solvation (O1W). The central Sm^III ion is nine-coordinate with four O-donor atoms from separate bidentate bridging ox ligands and five O-donors from the two ina ligands (both bidentate) [Sm—O bond length range, 2.389 (4)–2.791 (4) Å], giving a distorted monocapped square antiprismatic stereochemistry. The three-coordinate Ag^Iion is surrounded by two N-donor atoms from the two ina ligands [Ag–N, 2.181 (6), 2.185 (5) Å] and one O atom from a bridging oxalate ligand giving a T-shaped coordination geometry. The Ag—O bond [2.620 (4) Å] is long but this and the N—Ag—N angle [154.3 (2)°] are similar to those found in other Ag^I complexes having T-shaped configurations. The oxalate ligands bridge Sm centers to form a two-dimensional lanthanide-oxalate layered network. In the packing arrangement of the title compound, 'linear' N–Ag–N linkages play an important role in connecting the adjacent two-dimensional layers, forming a three-dimensional pillar-layered coordination polymer with microporous structures. Topological studies performed using the software package TOPOS 4.0 (Blatov & Shevchenko, 2006; Blatov et al., 2000) reveal that this topology is a unique five-nodal (3,4,6)-connected net. The water molecule of solvation also gives O–H···O hydrogen-bonding interactions with oxalate and isonicotinate O acceptors (Table 1).

Related literature top

For microporous metal-organic framework (MMOF) compounds, see: Sun et al. (2006); Wu & Lin (2005); Cho et al. (2006). For isonicotinic acid-heterometallic compounds, see: Cai et al. (2009); Gu & Xue (2006, 2007); Ma et al. (2009). For topological studies, see: Blatov et al. (2000); Blatov & Shevchenko (2006).

Experimental top

A mixture of isonicotinic acid (0.0615 g), Sm(NO₃)₃.6H₂O (0.114 g), AgNO₃ (0.051 g, 0.3mmol), oxalic acid dihydrate (0.037 g, 0.3mmol) and water (10 ml) was heated at 430 K for 72 h in a 23 ml Teflon-lined stainless-steel autoclave and then cooled to room temperature at a rate of 278° per hour. Colourless prismatic crystals were collected, washed with water three times and dried in air.

Computing details top

Data collection: SMART (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Displacement ellipsoid plot (40% probability level) of the title compound, with atom numbering scheme for non-H atoms. For symmetry-generated atoms, codes are: (A) -x + 1, y, -z - 1/2; (B) -x + 1, -y, -z; (C) -x + 1, -y + 1, -z; (D) -x + 1/2, y - 1/2,-z + 1/2; (E) x + 1/2,-y + 3/2, z - 1/2; (F) x - 1/2, y + 1/2, z].
	Fig. 2. The three-dimensional pillar-layered structure in a packing diagram of the title compound, with H atoms omitted for clarity. Hydrogen bonds are shown as dashed lines.

catena-Poly[[tetra-µ₃-isonicotinato-µ₃-oxalato-µ₂-oxalato- disamarium(III)disilver(I)] dihydrate] top

Crystal data top

[AgSm(C₆H₄NO₂)₂(C₂O₄)]·H₂O	F(000) = 2312
M_r = 608.47	D_x = 2.440 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3815 reflections
a = 22.0484 (18) Å	θ = 2.4–27.8°
b = 9.2372 (8) Å	µ = 4.75 mm⁻¹
c = 17.1137 (14) Å	T = 298 K
β = 108.123 (1)°	Prism, colorless
V = 3312.6 (5) Å³	0.30 × 0.23 × 0.18 mm
Z = 8

Data collection top

Bruker SMART APEX CCD-detector diffractometer	3240 independent reflections
Radiation source: fine-focus sealed tube	2789 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
ω scans	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −27→27
T_min = 0.330, T_max = 0.482	k = −11→11
8766 measured reflections	l = −16→21

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0301P)² + 2.6943P] where P = (F_o² + 2F_c²)/3
3240 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 1.43 e Å⁻³
0 restraints	Δρ_min = −1.50 e Å⁻³

Crystal data top

[AgSm(C₆H₄NO₂)₂(C₂O₄)]·H₂O	V = 3312.6 (5) Å³
M_r = 608.47	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 22.0484 (18) Å	µ = 4.75 mm⁻¹
b = 9.2372 (8) Å	T = 298 K
c = 17.1137 (14) Å	0.30 × 0.23 × 0.18 mm
β = 108.123 (1)°

Data collection top

Bruker SMART APEX CCD-detector diffractometer	3240 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2789 reflections with I > 2σ(I)
T_min = 0.330, T_max = 0.482	R_int = 0.057
8766 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.08	Δρ_max = 1.43 e Å⁻³
3240 reflections	Δρ_min = −1.50 e Å⁻³
244 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.17077 (3)	0.56369 (8)	0.13601 (4)	0.0685 (2)
C1	0.5352 (2)	0.0142 (5)	0.0244 (3)	0.0262 (11)
C2	0.5364 (2)	0.2525 (5)	−0.2303 (3)	0.0240 (11)
C3	0.3774 (2)	0.4799 (6)	−0.0550 (3)	0.0278 (11)
C4	0.3236 (3)	0.5115 (6)	−0.0213 (3)	0.0317 (12)
C5	0.2693 (4)	0.4269 (10)	−0.0417 (6)	0.082 (3)
H5	0.2627	0.3567	−0.0825	0.098*
C6	0.3283 (3)	0.6170 (8)	0.0352 (5)	0.0520 (18)
H6	0.3623	0.6817	0.0473	0.062*
C7	0.2830 (3)	0.6284 (8)	0.0745 (4)	0.0527 (19)
H7	0.2884	0.6992	0.1148	0.063*
C8	0.2246 (4)	0.4474 (10)	−0.0008 (6)	0.086 (3)
H8	0.1878	0.3910	−0.0155	0.103*
C9	0.1123 (4)	0.5823 (7)	0.2779 (5)	0.064 (2)
H9	0.1160	0.4822	0.2760	0.077*
C10	0.1345 (3)	0.8035 (7)	0.2388 (4)	0.0437 (16)
H10	0.1547	0.8615	0.2101	0.052*
C11	0.1016 (3)	0.8711 (7)	0.2855 (4)	0.0408 (15)
H11	0.0985	0.9714	0.2866	0.049*
C12	0.0803 (3)	0.6383 (7)	0.3267 (4)	0.0490 (18)
H12	0.0630	0.5773	0.3574	0.059*
C13	0.0734 (3)	0.7849 (6)	0.3305 (3)	0.0255 (11)
C14	0.0374 (2)	0.8525 (6)	0.3833 (3)	0.0262 (11)
N1	0.1388 (2)	0.6622 (6)	0.2325 (3)	0.0420 (13)
N2	0.2324 (3)	0.5447 (6)	0.0585 (3)	0.0492 (14)
O1	0.0347 (2)	0.7806 (4)	0.4442 (2)	0.0353 (9)
O2	0.01455 (19)	0.9765 (4)	0.3628 (2)	0.0337 (9)
O3	0.37193 (18)	0.3777 (5)	−0.1045 (2)	0.0388 (10)
O4	0.42816 (17)	0.5524 (4)	−0.0283 (2)	0.0316 (8)
O5	0.56218 (17)	−0.0747 (4)	0.0790 (2)	0.0286 (8)
O6	0.55987 (17)	0.1263 (4)	0.0070 (2)	0.0307 (8)
O7	0.55695 (18)	0.2331 (4)	−0.1546 (2)	0.0332 (9)
O8	0.56874 (17)	0.2685 (4)	−0.2785 (2)	0.0309 (8)
O1W	0.2965 (3)	0.1982 (6)	−0.2401 (4)	0.0729 (17)
H1W	0.3311	0.2196	−0.2506	0.109*
H2W	0.2925	0.2570	−0.2031	0.109*
Sm1	0.487549 (12)	0.31384 (3)	−0.073228 (15)	0.02264 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0488 (3)	0.1075 (6)	0.0651 (4)	−0.0103 (3)	0.0408 (3)	−0.0402 (4)
C1	0.037 (3)	0.022 (3)	0.025 (3)	−0.004 (2)	0.017 (2)	−0.005 (2)
C2	0.036 (3)	0.016 (3)	0.027 (3)	0.000 (2)	0.020 (2)	0.000 (2)
C3	0.027 (3)	0.035 (3)	0.022 (3)	0.002 (2)	0.010 (2)	0.003 (2)
C4	0.029 (3)	0.041 (3)	0.031 (3)	−0.004 (2)	0.017 (2)	−0.003 (2)
C5	0.063 (5)	0.109 (7)	0.099 (7)	−0.046 (5)	0.061 (5)	−0.083 (6)
C6	0.036 (3)	0.056 (4)	0.071 (5)	−0.012 (3)	0.027 (3)	−0.032 (4)
C7	0.037 (3)	0.067 (5)	0.057 (4)	−0.006 (3)	0.020 (3)	−0.037 (4)
C8	0.068 (5)	0.110 (8)	0.109 (7)	−0.049 (5)	0.070 (5)	−0.069 (6)
C9	0.090 (6)	0.031 (4)	0.104 (6)	−0.011 (3)	0.080 (5)	−0.017 (4)
C10	0.048 (4)	0.054 (4)	0.042 (4)	0.001 (3)	0.032 (3)	0.006 (3)
C11	0.056 (4)	0.033 (3)	0.047 (4)	0.011 (3)	0.035 (3)	0.016 (3)
C12	0.072 (5)	0.028 (3)	0.072 (5)	−0.007 (3)	0.059 (4)	−0.005 (3)
C13	0.031 (3)	0.030 (3)	0.018 (2)	0.003 (2)	0.013 (2)	0.001 (2)
C14	0.030 (3)	0.027 (3)	0.028 (3)	−0.001 (2)	0.017 (2)	−0.005 (2)
N1	0.045 (3)	0.049 (3)	0.044 (3)	−0.006 (2)	0.031 (3)	−0.018 (2)
N2	0.045 (3)	0.066 (4)	0.051 (3)	−0.001 (3)	0.034 (3)	−0.016 (3)
O1	0.052 (3)	0.033 (2)	0.030 (2)	0.0029 (18)	0.0265 (19)	0.0004 (17)
O2	0.050 (2)	0.028 (2)	0.030 (2)	0.0086 (17)	0.0228 (18)	−0.0002 (16)
O3	0.035 (2)	0.050 (3)	0.037 (2)	−0.0027 (18)	0.0180 (18)	−0.015 (2)
O4	0.0268 (19)	0.036 (2)	0.035 (2)	−0.0004 (17)	0.0138 (16)	0.0022 (17)
O5	0.035 (2)	0.0238 (19)	0.028 (2)	−0.0042 (15)	0.0108 (16)	0.0055 (15)
O6	0.030 (2)	0.026 (2)	0.040 (2)	−0.0057 (16)	0.0180 (17)	0.0028 (17)
O7	0.039 (2)	0.041 (2)	0.025 (2)	0.0037 (18)	0.0167 (17)	0.0006 (17)
O8	0.033 (2)	0.035 (2)	0.033 (2)	0.0030 (16)	0.0217 (17)	0.0026 (17)
O1W	0.058 (3)	0.081 (4)	0.080 (4)	−0.006 (3)	0.022 (3)	−0.011 (3)
Sm1	0.02976 (18)	0.02037 (18)	0.02401 (18)	−0.00243 (10)	0.01742 (13)	−0.00082 (9)

Geometric parameters (Å, º) top

Sm1—O3	2.507 (4)	N1—C9	1.331 (10)
Sm1—O4	2.791 (4)	N2—C8	1.326 (11)
Sm1—O6	2.463 (4)	N2—C7	1.314 (10)
Sm1—O7	2.483 (4)	C1—C1ⁱⁱ	1.539 (7)
Sm1—O8ⁱ	2.489 (3)	C2—C2ⁱ	1.536 (7)
Sm1—O5ⁱⁱ	2.454 (4)	C3—C4	1.500 (8)
Sm1—O4ⁱⁱⁱ	2.448 (4)	C4—C6	1.354 (9)
Sm1—O1^iv	2.426 (4)	C4—C5	1.381 (11)
Sm1—O2^v	2.389 (4)	C5—C8	1.388 (13)
Ag1—N1	2.185 (5)	C6—C7	1.371 (10)
Ag1—N2	2.181 (6)	C9—C12	1.353 (11)
Ag1—O5^vi	2.620 (4)	C10—C11	1.384 (10)
O1—C14	1.253 (6)	C11—C13	1.383 (9)
O2—C14	1.257 (7)	C12—C13	1.367 (9)
O3—C3	1.249 (7)	C13—C14	1.511 (8)
O4—C3	1.262 (6)	C5—H5	0.9300
O5—C1	1.247 (6)	C6—H6	0.9300
O6—C1	1.248 (6)	C7—H7	0.9300
O7—C2	1.245 (6)	C8—H8	0.9300
O8—C2	1.256 (6)	C9—H9	0.9300
O1W—H2W	0.8600	C10—H10	0.9300
O1W—H1W	0.8600	C11—H11	0.9300
N1—C10	1.316 (9)	C12—H12	0.9300

O3—Sm1—O4	48.69 (12)	Sm1ⁱ—O8—C2	119.0 (3)
O3—Sm1—O6	136.35 (13)	H1W—O1W—H2W	108.00
O3—Sm1—O7	135.58 (11)	Ag1—N1—C9	120.9 (5)
O3—Sm1—O8ⁱ	70.76 (12)	Ag1—N1—C10	121.6 (4)
O3—Sm1—O5ⁱⁱ	77.95 (14)	C9—N1—C10	116.5 (6)
O3—Sm1—O4ⁱⁱⁱ	122.00 (13)	Ag1—N2—C8	124.3 (6)
O1^iv—Sm1—O3	75.17 (13)	C7—N2—C8	117.2 (7)
O2^v—Sm1—O3	95.35 (14)	Ag1—N2—C7	118.4 (4)
O4—Sm1—O6	132.82 (10)	O5—C1—O6	125.7 (5)
O4—Sm1—O7	144.66 (11)	O6—C1—C1ⁱⁱ	116.9 (4)
O4—Sm1—O8ⁱ	106.61 (11)	O5—C1—C1ⁱⁱ	117.4 (4)
O4—Sm1—O5ⁱⁱ	118.67 (12)	O7—C2—O8	127.1 (5)
O4—Sm1—O4ⁱⁱⁱ	73.95 (12)	O8—C2—C2ⁱ	116.2 (4)
O1^iv—Sm1—O4	66.68 (11)	O7—C2—C2ⁱ	116.7 (4)
O2^v—Sm1—O4	72.02 (12)	O3—C3—O4	122.3 (5)
O6—Sm1—O7	72.32 (12)	O3—C3—C4	119.1 (5)
O6—Sm1—O8ⁱ	118.75 (12)	O4—C3—C4	118.4 (5)
O5ⁱⁱ—Sm1—O6	65.99 (12)	C3—C4—C5	121.3 (6)
O4ⁱⁱⁱ—Sm1—O6	75.07 (12)	C3—C4—C6	121.4 (6)
O1^iv—Sm1—O6	71.50 (13)	C5—C4—C6	117.1 (7)
O2^v—Sm1—O6	127.96 (13)	C4—C5—C8	119.4 (8)
O7—Sm1—O8ⁱ	64.94 (12)	C4—C6—C7	120.0 (7)
O5ⁱⁱ—Sm1—O7	93.02 (12)	N2—C7—C6	123.6 (7)
O4ⁱⁱⁱ—Sm1—O7	94.90 (12)	N2—C8—C5	122.3 (8)
O1^iv—Sm1—O7	143.81 (13)	N1—C9—C12	123.8 (6)
O2^v—Sm1—O7	72.64 (13)	N1—C10—C11	124.0 (6)
O5ⁱⁱ—Sm1—O8ⁱ	74.50 (11)	C10—C11—C13	118.0 (6)
O4ⁱⁱⁱ—Sm1—O8ⁱ	146.76 (12)	C9—C12—C13	119.7 (6)
O1^iv—Sm1—O8ⁱ	136.79 (13)	C11—C13—C14	120.4 (5)
O2^v—Sm1—O8ⁱ	77.62 (12)	C12—C13—C14	121.7 (5)
O4ⁱⁱⁱ—Sm1—O5ⁱⁱ	135.56 (11)	C11—C13—C12	117.9 (6)
O1^iv—Sm1—O5ⁱⁱ	73.05 (12)	O1—C14—O2	126.6 (5)
O2^v—Sm1—O5ⁱⁱ	151.99 (11)	O2—C14—C13	116.7 (4)
O1^iv—Sm1—O4ⁱⁱⁱ	75.03 (13)	O1—C14—C13	116.6 (5)
O2^v—Sm1—O4ⁱⁱⁱ	70.96 (12)	C4—C5—H5	120.00
O1^iv—Sm1—O2^v	132.02 (12)	C8—C5—H5	120.00
N1—Ag1—N2	154.3 (2)	C7—C6—H6	120.00
O5^vi—Ag1—N1	90.71 (15)	C4—C6—H6	120.00
O5^vi—Ag1—N2	113.85 (17)	N2—C7—H7	118.00
Sm1^vii—O1—C14	140.0 (3)	C6—C7—H7	118.00
Sm1^viii—O2—C14	138.3 (3)	C5—C8—H8	119.00
Sm1—O3—C3	99.0 (3)	N2—C8—H8	119.00
Sm1—O4—C3	85.4 (3)	N1—C9—H9	118.00
Sm1—O4—Sm1ⁱⁱⁱ	106.05 (13)	C12—C9—H9	118.00
Sm1ⁱⁱⁱ—O4—C3	156.5 (3)	C11—C10—H10	118.00
Sm1ⁱⁱ—O5—C1	117.4 (3)	N1—C10—H10	118.00
Ag1^ix—O5—C1	97.2 (3)	C10—C11—H11	121.00
Sm1ⁱⁱ—O5—Ag1^ix	143.05 (16)	C13—C11—H11	121.00
Sm1—O6—C1	117.5 (3)	C9—C12—H12	120.00
Sm1—O7—C2	116.9 (3)	C13—C12—H12	120.00

O8ⁱ—Sm1—O6—C1	−72.4 (4)	O3ⁱ—Sm1ⁱ—O8—C2	164.2 (4)
O5ⁱⁱ—Sm1—O6—C1	−17.8 (3)	O4ⁱ—Sm1ⁱ—O8—C2	130.7 (3)
O4ⁱⁱⁱ—Sm1—O6—C1	140.3 (4)	O5^vi—Ag1—N1—C9	47.9 (5)
O1^iv—Sm1—O6—C1	61.4 (3)	N1—Ag1—O5^vi—C1^vi	95.8 (3)
O2^v—Sm1—O6—C1	−169.2 (3)	N2—Ag1—O5^vi—C1^vi	−76.5 (3)
O3—Sm1—O7—C2	17.4 (4)	O5^vi—Ag1—N1—C10	−120.1 (5)
O4—Sm1—O7—C2	−61.6 (4)	N1—Ag1—N2—C7	7.2 (8)
O6—Sm1—O7—C2	156.9 (4)	N1—Ag1—N2—C8	−177.3 (6)
O8ⁱ—Sm1—O7—C2	21.9 (3)	O5^vi—Ag1—N2—C7	169.2 (5)
O5ⁱⁱ—Sm1—O7—C2	93.3 (3)	O5^vi—Ag1—N2—C8	−15.3 (7)
O3^vii—Sm1^vii—O1—C14	−84.5 (6)	N2—Ag1—N1—C9	−148.6 (6)
O4^vii—Sm1^vii—O1—C14	−33.5 (5)	N2—Ag1—N1—C10	43.5 (7)
O6^vii—Sm1^vii—O1—C14	124.1 (6)	Sm1^vii—O1—C14—C13	161.8 (4)
O7^vii—Sm1^vii—O1—C14	122.7 (5)	Sm1^vii—O1—C14—O2	−16.4 (9)
O4^viii—Sm1^vii—O1—C14	45.2 (5)	Sm1^viii—O2—C14—O1	26.0 (9)
O4^vii—Sm1^viii—O2—C14	26.1 (5)	Sm1^viii—O2—C14—C13	−152.2 (4)
O3^viii—Sm1^viii—O2—C14	−95.9 (5)	Sm1—O3—C3—C4	−151.9 (4)
O4^viii—Sm1^viii—O2—C14	−52.6 (5)	Sm1—O3—C3—O4	23.7 (5)
O6^viii—Sm1^viii—O2—C14	78.2 (5)	Sm1—O4—C3—O3	−21.0 (5)
O7^viii—Sm1^viii—O2—C14	127.8 (5)	Sm1ⁱⁱⁱ—O4—C3—C4	33.8 (11)
O4—Sm1—O3—C3	−11.8 (3)	Sm1ⁱⁱⁱ—O4—C3—O3	−141.8 (7)
O6—Sm1—O3—C3	101.1 (4)	Sm1—O4—C3—C4	154.7 (4)
O7—Sm1—O3—C3	−142.7 (3)	Sm1ⁱⁱ—O5—C1—O6	−163.5 (4)
O8ⁱ—Sm1—O3—C3	−147.0 (3)	Ag1^ix—O5—C1—C1ⁱⁱ	−175.3 (3)
O5ⁱⁱ—Sm1—O3—C3	135.4 (3)	Ag1^ix—O5—C1—O6	3.0 (5)
O4ⁱⁱⁱ—Sm1—O3—C3	−1.3 (4)	Sm1ⁱⁱ—O5—C1—C1ⁱⁱ	18.3 (5)
O1^iv—Sm1—O3—C3	60.0 (3)	Sm1—O6—C1—O5	−162.4 (4)
O2^v—Sm1—O3—C3	−72.1 (3)	Sm1—O6—C1—C1ⁱⁱ	15.9 (5)
O3—Sm1—O4—C3	11.6 (3)	Sm1—O7—C2—O8	153.3 (4)
O6—Sm1—O4—C3	−108.4 (3)	Sm1—O7—C2—C2ⁱ	−28.7 (5)
O7—Sm1—O4—C3	125.4 (3)	Sm1ⁱ—O8—C2—C2ⁱ	4.0 (5)
O8ⁱ—Sm1—O4—C3	55.5 (3)	Sm1ⁱ—O8—C2—O7	−177.9 (4)
O5ⁱⁱ—Sm1—O4—C3	−25.6 (3)	Ag1—N1—C9—C12	−166.4 (6)
O4ⁱⁱⁱ—Sm1—O4—C3	−159.2 (3)	C10—N1—C9—C12	2.2 (11)
O1^iv—Sm1—O4—C3	−78.9 (3)	Ag1—N1—C10—C11	164.8 (5)
O2^v—Sm1—O4—C3	126.1 (3)	C9—N1—C10—C11	−3.7 (10)
O3—Sm1—O4—Sm1ⁱⁱⁱ	170.7 (2)	Ag1—N2—C8—C5	−171.7 (7)
O6—Sm1—O4—Sm1ⁱⁱⁱ	50.8 (2)	Ag1—N2—C7—C6	173.7 (6)
O7—Sm1—O4—Sm1ⁱⁱⁱ	−75.4 (2)	C7—N2—C8—C5	3.8 (12)
O8ⁱ—Sm1—O4—Sm1ⁱⁱⁱ	−145.32 (13)	C8—N2—C7—C6	−2.1 (11)
O5ⁱⁱ—Sm1—O4—Sm1ⁱⁱⁱ	133.58 (13)	O6—C1—C1ⁱⁱ—O6ⁱⁱ	180.0 (4)
O4ⁱⁱⁱ—Sm1—O4—Sm1ⁱⁱⁱ	0.02 (14)	O5—C1—C1ⁱⁱ—O6ⁱⁱ	−1.6 (7)
O1^iv—Sm1—O4—Sm1ⁱⁱⁱ	80.28 (15)	O6—C1—C1ⁱⁱ—O5ⁱⁱ	1.6 (7)
O2^v—Sm1—O4—Sm1ⁱⁱⁱ	−74.72 (14)	O5—C1—C1ⁱⁱ—O5ⁱⁱ	180.0 (4)
O3ⁱⁱⁱ—Sm1ⁱⁱⁱ—O4—Sm1	8.21 (18)	O7—C2—C2ⁱ—O8ⁱ	16.8 (6)
O4ⁱⁱⁱ—Sm1ⁱⁱⁱ—O4—Sm1	0.00 (11)	O8—C2—C2ⁱ—O7ⁱ	16.8 (6)
O6ⁱⁱⁱ—Sm1ⁱⁱⁱ—O4—Sm1	143.96 (15)	O7—C2—C2ⁱ—O7ⁱ	−161.5 (4)
O7ⁱⁱⁱ—Sm1ⁱⁱⁱ—O4—Sm1	−145.82 (12)	O8—C2—C2ⁱ—O8ⁱ	−164.9 (4)
O2^iv—Sm1ⁱⁱⁱ—O4—Sm1	−76.09 (14)	O3—C3—C4—C6	177.1 (6)
O1^v—Sm1ⁱⁱⁱ—O4—Sm1	69.54 (13)	O3—C3—C4—C5	2.3 (9)
O3ⁱⁱⁱ—Sm1ⁱⁱⁱ—O4—C3	125.3 (9)	O4—C3—C4—C6	1.3 (8)
O4ⁱⁱⁱ—Sm1ⁱⁱⁱ—O4—C3	117.0 (9)	O4—C3—C4—C5	−173.5 (6)
O6ⁱⁱⁱ—Sm1ⁱⁱⁱ—O4—C3	−99.0 (9)	C6—C4—C5—C8	−3.7 (12)
O7ⁱⁱⁱ—Sm1ⁱⁱⁱ—O4—C3	−28.8 (9)	C3—C4—C6—C7	−169.6 (6)
O2^iv—Sm1ⁱⁱⁱ—O4—C3	41.0 (9)	C3—C4—C5—C8	171.3 (7)
O1^v—Sm1ⁱⁱⁱ—O4—C3	−173.4 (9)	C5—C4—C6—C7	5.5 (10)
O3ⁱⁱ—Sm1ⁱⁱ—O5—C1	136.2 (4)	C4—C5—C8—N2	−0.9 (14)
O4ⁱⁱ—Sm1ⁱⁱ—O5—C1	108.6 (3)	C4—C6—C7—N2	−2.7 (11)
O6ⁱⁱ—Sm1ⁱⁱ—O5—C1	−18.6 (3)	N1—C9—C12—C13	0.6 (12)
O7ⁱⁱ—Sm1ⁱⁱ—O5—C1	−87.7 (3)	N1—C10—C11—C13	2.3 (10)
O3—Sm1—O6—C1	19.3 (4)	C10—C11—C13—C12	0.6 (9)
O4—Sm1—O6—C1	89.9 (4)	C10—C11—C13—C14	179.4 (5)
O7—Sm1—O6—C1	−119.4 (4)	C9—C12—C13—C11	−2.0 (10)
O6ⁱ—Sm1ⁱ—O8—C2	−62.8 (4)	C9—C12—C13—C14	179.3 (6)
O7ⁱ—Sm1ⁱ—O8—C2	−12.5 (3)	C11—C13—C14—O2	25.2 (8)
O2^v—Sm1—O7—C2	−62.2 (3)	C12—C13—C14—O1	25.6 (8)
O4ⁱⁱⁱ—Sm1—O7—C2	−130.5 (3)	C12—C13—C14—O2	−156.1 (6)
O1^iv—Sm1—O7—C2	158.3 (3)	C11—C13—C14—O1	−153.1 (6)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O8ⁱ	0.86	2.16	2.960 (8)	156
O1W—H2W···O3	0.86	2.31	2.915 (7)	128

Symmetry code: (i) −x+1, y, −z−1/2.

Experimental details

Crystal data
Chemical formula	[AgSm(C₆H₄NO₂)₂(C₂O₄)]·H₂O
M_r	608.47
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	22.0484 (18), 9.2372 (8), 17.1137 (14)
β (°)	108.123 (1)
V (Å³)	3312.6 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	4.75
Crystal size (mm)	0.30 × 0.23 × 0.18

Data collection
Diffractometer	Bruker SMART APEX CCD-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.330, 0.482
No. of measured, independent and observed [I > 2σ(I)] reflections	8766, 3240, 2789
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.097, 1.08
No. of reflections	3240
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.43, −1.50

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O8ⁱ	0.86	2.16	2.960 (8)	156
O1W—H2W···O3	0.86	2.31	2.915 (7)	128

Symmetry code: (i) −x+1, y, −z−1/2.

Acknowledgements

This work was financially supported by Guangdong Provincial Science and Technology Bureau (grant No. 2008B010600009), and NSFC (grant Nos. U0734005 and 20971047).

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