catena-Poly[[tetra-μ(3)-isonicotinato-μ(3)-oxalato-μ(2)-oxalato-disamarium(III)disilver(I)] dihydrate].

In the title compound, {[AgSm(C(6)H(4)NO(2))(2)(C(2)O(4))]·H(2)O}(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 mol-ecule. 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 anti-prismatic 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. Inter-molecular water-carboxyl-ate O-H⋯O hydrogen-bonding inter-actions 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 n class="Chemical">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)]·n class="Chemical">H2O

M = 608.47

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.097

S = 1.08

3240 reflections

244 parameters

H-atom parameters constrained

Δρmax = 1.43 e Å−3

Δρmin = −1.50 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[AgSm(C6H4NO2)2(C2O4)]·H2O	F(000) = 2312
Mr = 608.47	Dx = 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

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

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(Fo2) + (0.0301P)2 + 2.6943P] where P = (Fo2 + 2Fc2)/3
3240 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 1.43 e Å−3
0 restraints	Δρmin = −1.50 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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—O1iv	2.426 (4)	C4—C5	1.381 (11)
Sm1—O2v	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—O5vi	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)
O1iv—Sm1—O3	75.17 (13)	C7—N2—C8	117.2 (7)
O2v—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)
O1iv—Sm1—O4	66.68 (11)	O7—C2—C2i	116.7 (4)
O2v—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)
O1iv—Sm1—O6	71.50 (13)	C5—C4—C6	117.1 (7)
O2v—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)
O1iv—Sm1—O7	143.81 (13)	N1—C9—C12	123.8 (6)
O2v—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)
O1iv—Sm1—O8i	136.79 (13)	C11—C13—C14	120.4 (5)
O2v—Sm1—O8i	77.62 (12)	C12—C13—C14	121.7 (5)
O4iii—Sm1—O5ii	135.56 (11)	C11—C13—C12	117.9 (6)
O1iv—Sm1—O5ii	73.05 (12)	O1—C14—O2	126.6 (5)
O2v—Sm1—O5ii	151.99 (11)	O2—C14—C13	116.7 (4)
O1iv—Sm1—O4iii	75.03 (13)	O1—C14—C13	116.6 (5)
O2v—Sm1—O4iii	70.96 (12)	C4—C5—H5	120.00
O1iv—Sm1—O2v	132.02 (12)	C8—C5—H5	120.00
N1—Ag1—N2	154.3 (2)	C7—C6—H6	120.00
O5vi—Ag1—N1	90.71 (15)	C4—C6—H6	120.00
O5vi—Ag1—N2	113.85 (17)	N2—C7—H7	118.00
Sm1vii—O1—C14	140.0 (3)	C6—C7—H7	118.00
Sm1viii—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
Ag1ix—O5—C1	97.2 (3)	C10—C11—H11	121.00
Sm1ii—O5—Ag1ix	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)	O5vi—Ag1—N1—C9	47.9 (5)
O1iv—Sm1—O6—C1	61.4 (3)	N1—Ag1—O5vi—C1vi	95.8 (3)
O2v—Sm1—O6—C1	−169.2 (3)	N2—Ag1—O5vi—C1vi	−76.5 (3)
O3—Sm1—O7—C2	17.4 (4)	O5vi—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)	O5vi—Ag1—N2—C7	169.2 (5)
O5ii—Sm1—O7—C2	93.3 (3)	O5vi—Ag1—N2—C8	−15.3 (7)
O3vii—Sm1vii—O1—C14	−84.5 (6)	N2—Ag1—N1—C9	−148.6 (6)
O4vii—Sm1vii—O1—C14	−33.5 (5)	N2—Ag1—N1—C10	43.5 (7)
O6vii—Sm1vii—O1—C14	124.1 (6)	Sm1vii—O1—C14—C13	161.8 (4)
O7vii—Sm1vii—O1—C14	122.7 (5)	Sm1vii—O1—C14—O2	−16.4 (9)
O4viii—Sm1vii—O1—C14	45.2 (5)	Sm1viii—O2—C14—O1	26.0 (9)
O4vii—Sm1viii—O2—C14	26.1 (5)	Sm1viii—O2—C14—C13	−152.2 (4)
O3viii—Sm1viii—O2—C14	−95.9 (5)	Sm1—O3—C3—C4	−151.9 (4)
O4viii—Sm1viii—O2—C14	−52.6 (5)	Sm1—O3—C3—O4	23.7 (5)
O6viii—Sm1viii—O2—C14	78.2 (5)	Sm1—O4—C3—O3	−21.0 (5)
O7viii—Sm1viii—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)	Ag1ix—O5—C1—C1ii	−175.3 (3)
O5ii—Sm1—O3—C3	135.4 (3)	Ag1ix—O5—C1—O6	3.0 (5)
O4iii—Sm1—O3—C3	−1.3 (4)	Sm1ii—O5—C1—C1ii	18.3 (5)
O1iv—Sm1—O3—C3	60.0 (3)	Sm1—O6—C1—O5	−162.4 (4)
O2v—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)
O1iv—Sm1—O4—C3	−78.9 (3)	Ag1—N1—C10—C11	164.8 (5)
O2v—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)
O1iv—Sm1—O4—Sm1iii	80.28 (15)	O6—C1—C1ii—O5ii	1.6 (7)
O2v—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)
O2iv—Sm1iii—O4—Sm1	−76.09 (14)	O3—C3—C4—C6	177.1 (6)
O1v—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)
O2iv—Sm1iii—O4—C3	41.0 (9)	C3—C4—C5—C8	171.3 (7)
O1v—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)
O2v—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)
O1iv—Sm1—O7—C2	158.3 (3)	C11—C13—C14—O1	−153.1 (6)

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

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) .