Poly[[(μ₂-acetato-κ³O,O′:O′)aqua­bis­(μ₃-isonicotinato-κ³O:O′:N)samarium(III)silver(I)] perchlorate]

The title compound, {[AgSm(C₆H₄NO₂)₂(CH₃CO₂)(H₂O)]ClO₄}_n, is a three-dimensional heterobimetallic complex constructed from a repeating dimeric unit. Only half of the dimeric moiety is found in the asymmetric unit; the unit cell is completed by crystallographic inversion symmetry. The Sm^III ion is eight-coordinated by four O atoms of four different isonicotinate ligands, three O atoms of two different acetate ligands, and one O atom of a water mol­ecule. The two-coordinate Ag^I ion is bonded to two N atoms of two different isonicotinate anions, thereby connecting the disamarium units. In addition, the isonicotinate ligands also act as bridging ligands, generating a three-dimensional network. The coordinated water mol­ecules link the carboxyl­ate group and acetate ligands by O—H...O hydrogen bonding. Another O—H...O hydrogen bond is observed in the crystal structure. The perchlorate ion is disordered over two sites with site-occupancy factors of 0.560 (11) and 0.440 (11), whereas the methyl group of the acetate ligand is disordered over two sites with site-occupancy factors of 0.53 (5) and 0.47 (5).

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in main residue
• R factor = 0.026
• wR factor = 0.064
• Data-to-parameter ratio = 11.0

checkCIF/PLATON results

No syntax errors found



Alert level C
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        Sm1
PLAT774_ALERT_1_C Suspect X-Y Bond in CIF:   SM1    --  SM1     ..       3.93 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.599          3

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         16
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained Atom Sites ....         10
PLAT004_ALERT_5_G Info: Polymeric Structure Found with Dimension .          1
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT301_ALERT_3_G Note: Main Residue  Disorder ...................          4 Perc.
PLAT302_ALERT_4_G Note: Anion/Solvent Disorder ...................        100 Perc.
PLAT432_ALERT_2_G Short Inter X...Y Contact  C4     ..  O9      ..       3.01 Ang.
PLAT432_ALERT_2_G Short Inter X...Y Contact  C9     ..  O8      ..       2.80 Ang.
PLAT432_ALERT_2_G Short Inter X...Y Contact  C10    ..  O8      ..       3.00 Ang.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #        105
              C14  -C13  -C14'    1.555   1.555   1.555             16.70 Deg.
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          !
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......        158
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          65 Perc.

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  13 ALERT level G = General information/check it is not something unexpected

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

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S1. Comment

In the past few years, lanthanide-transition metal heterometallic complexes with bridging multifunctional 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 as luminescent probes (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 heterobimetallic coordination polymer, (I), has been determined which is presented in this artcle.

The polymer of the title compound displays a three-dimensional heterometallic coordination framework constructed from the repeating dimeric unit. Only half of the dimeric unit is found in the asymmetric unit whose center is a crystallographic center of inversion (Fig. 1). The asymmetric unit of the title compound, contains one of the Sm^III and Ag^I ions each, two halves of the acetate ligands, two isonicotinate ligands and one coordinated water molecule. The Sm^III ion is eight-coordinated by four O atoms of four different isonicotinate ligands, three O atoms of two different acetate ligands and one O atom of a water molecule. The Sm center can therefore be described as adopting a bicapped trigonal prismatic coordination geometry. The two-coordinate Ag^I ion is bonded to two N atoms of two different isonicotinate anions. The Ag^I ion shows an almost linear coordination with N1—Ag1—N2 being 166.2 (2) °. These metal coordination units are additionally 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). Another O–H···O hydrogen bond is observed in the crystal structure.

Related literature

For background to lanthanide–transition metal heterometallic complexes, see: Cheng et al. (2006); Kuang et al. (2007); Peng et al. (2008); Zhu et al. (2009).

S2. Experimental

A mixture of AgNO₃ (0.057 g, 0.33 mmol), Sm₂O₃ (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(yield: 45% based on Sm). Yellow block shaped crystals suitable for X-ray analysis were obtained.

S3. Refinement

H atoms bonded to C atoms were positioned geometrically and refined as riding, with C—H = 0.93 or 0.96 Å and U_iso(H) = 1.2 or 1.5 U_eq(C). H atoms of water molecules were found from difference Fourier maps and refined isotropically with a restraint of O—H = 0.82 Å. The perchlorate ion was disordered over two sites with site occupancy factors 0.560 (11) and 0.440 (11), whereas the methyl group of the acetate ligand was disordered over two sites with site occupancy factors 0.53 (5) and 0.47 (5).

Computing details

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

Figures

	Fig. 1. Molecular structure showing displacement ellipsoids drawn at the 30% probability level. Hydrogen atoms are omitted for clarity. Symmetry codes: (A) 1 - x, 1/2 + y, 2.5 - z; (B) x, 1.5 - y, 1/2 + z; (C) 2 - x, 2 - y, 2 - z.
	Fig. 2. A view of the three-dimensional structure of the title compound. Hydrogen atoms are omitted for clarity.

Poly[[(µ₂-acetato-κ³O,O':O')aquabis(µ₃- isonicotinato-κ³O:O':N)samarium(III)silver(I)] perchlorate]

Crystal data

[AgSm(C6H4NO2)2(C2H3O2)(H2O)]ClO4	F(000) = 1300
Mr = 678.94	Dx = 2.315 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3844 reflections
a = 16.1703 (15) Å	θ = 2.5–27.3°
b = 15.1042 (14) Å	µ = 4.19 mm^−1
c = 7.9858 (7) Å	T = 296 K
β = 92.845 (1)°	Block, yellow
V = 1948.0 (3) Å^3	0.22 × 0.20 × 0.19 mm
Z = 4

Data collection

Bruker APEXII area-detector diffractometer	3512 independent reflections
Radiation source: fine-focus sealed tube	2957 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ϕ and ω scan	θmax = 25.2°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→19
Tmin = 0.414, Tmax = 0.451	k = −17→18
9927 measured reflections	l = −7→9

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.064	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0316P)^2 + 0.0621P] where P = (Fo^2 + 2Fc^2)/3
3512 reflections	(Δ/σ)max = 0.001
320 parameters	Δρmax = 0.85 e Å^−3
158 restraints	Δρmin = −0.59 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Sm1	0.952467 (14)	0.883640 (13)	1.04772 (3)	0.02097 (9)
Ag1	0.52807 (3)	1.23823 (4)	1.39951 (7)	0.06436 (17)
C1	0.8319 (3)	0.7509 (3)	0.7966 (5)	0.0243 (10)
C2	0.7476 (3)	0.7501 (3)	0.8658 (6)	0.0255 (10)
C3	0.7080 (3)	0.6710 (3)	0.8907 (6)	0.0357 (12)
H3	0.7332	0.6178	0.8639	0.043*
C4	0.6304 (3)	0.6710 (3)	0.9558 (7)	0.0465 (14)
H4	0.6042	0.6171	0.9726	0.056*
C5	0.6303 (3)	0.8222 (3)	0.9692 (6)	0.0388 (12)
H5	0.6037	0.8747	0.9948	0.047*
C6	0.7077 (3)	0.8270 (3)	0.9062 (6)	0.0331 (11)
H6	0.7328	0.8816	0.8911	0.040*
C7	0.8665 (3)	1.0831 (3)	1.1375 (7)	0.0367 (12)
C8	0.7883 (3)	1.1243 (3)	1.1940 (6)	0.0310 (11)
C9	0.7177 (3)	1.0739 (3)	1.2021 (7)	0.0414 (13)
H9	0.7186	1.0143	1.1728	0.050*
C10	0.6466 (4)	1.1114 (4)	1.2534 (8)	0.0529 (16)
H10	0.5991	1.0767	1.2566	0.064*
C11	0.7115 (3)	1.2455 (3)	1.2903 (8)	0.0475 (15)
H11	0.7096	1.3048	1.3216	0.057*
C12	0.7843 (3)	1.2127 (3)	1.2376 (7)	0.0431 (14)
H12	0.8304	1.2490	1.2310	0.052*
O1	0.8543 (2)	0.68433 (19)	0.7172 (4)	0.0336 (8)
O2	0.87650 (19)	0.81870 (18)	0.8220 (4)	0.0288 (7)
O3	0.8699 (2)	1.0005 (2)	1.1391 (5)	0.0493 (11)
O4	0.9236 (2)	1.1345 (2)	1.0941 (5)	0.0472 (11)
O5	0.9496 (2)	0.99873 (19)	0.8377 (4)	0.0375 (8)
O6	0.9636 (2)	1.1151 (2)	0.6844 (4)	0.0400 (9)
N1	0.5915 (3)	0.7460 (3)	0.9955 (6)	0.0420 (11)
N2	0.6427 (3)	1.1970 (3)	1.2995 (6)	0.0467 (12)
O1W	0.9949 (3)	0.72899 (19)	1.0725 (4)	0.0411 (9)
H2W	1.012 (3)	0.698 (2)	0.999 (5)	0.062*
H1W	0.974 (3)	0.696 (2)	1.138 (5)	0.062*
C13	0.9284 (3)	1.0421 (3)	0.7094 (6)	0.0305 (11)
C14	0.8508 (14)	1.0157 (19)	0.608 (3)	0.048 (4)	0.47 (5)
H14A	0.8496	0.9525	0.5953	0.071*	0.47 (5)
H14B	0.8506	1.0432	0.5000	0.071*	0.47 (5)
H14C	0.8031	1.0345	0.6656	0.071*	0.47 (5)
C14'	0.8691 (14)	1.0029 (16)	0.577 (3)	0.048 (4)	0.53 (5)
H14D	0.8380	1.0496	0.5221	0.071*	0.53 (5)
H14E	0.8318	0.9631	0.6293	0.071*	0.53 (5)
H14F	0.8997	0.9712	0.4966	0.071*	0.53 (5)
Cl1	0.58196 (10)	0.45830 (10)	0.2449 (2)	0.0586 (4)	0.440 (11)
O7	0.5413 (12)	0.5414 (9)	0.242 (2)	0.091 (8)	0.440 (11)
O8	0.6274 (10)	0.4512 (9)	0.3969 (14)	0.107 (6)	0.440 (11)
O9	0.5293 (9)	0.3894 (8)	0.216 (2)	0.123 (6)	0.440 (11)
O10	0.6425 (9)	0.4616 (9)	0.1148 (18)	0.124 (6)	0.440 (11)
Cl1'	0.58196 (10)	0.45830 (10)	0.2449 (2)	0.0586 (4)	0.560 (11)
O7'	0.5434 (8)	0.5371 (7)	0.201 (2)	0.080 (5)	0.560 (11)
O8'	0.6654 (5)	0.4696 (6)	0.2946 (18)	0.101 (4)	0.560 (11)
O9'	0.5408 (9)	0.4196 (8)	0.3857 (15)	0.139 (6)	0.560 (11)
O10'	0.5760 (8)	0.3951 (8)	0.1174 (13)	0.116 (5)	0.560 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sm1	0.02057 (14)	0.01549 (13)	0.02745 (14)	−0.00121 (9)	0.00717 (9)	−0.00001 (9)
Ag1	0.0295 (3)	0.0884 (4)	0.0776 (4)	0.0140 (2)	0.0260 (2)	−0.0008 (3)
C1	0.023 (3)	0.024 (2)	0.026 (2)	−0.0023 (19)	0.0013 (19)	0.0000 (19)
C2	0.023 (3)	0.026 (2)	0.028 (3)	−0.0038 (19)	0.0054 (19)	−0.0029 (19)
C3	0.031 (3)	0.028 (3)	0.049 (3)	−0.004 (2)	0.013 (2)	−0.005 (2)
C4	0.034 (3)	0.041 (3)	0.066 (4)	−0.010 (3)	0.011 (3)	0.002 (3)
C5	0.026 (3)	0.040 (3)	0.051 (3)	0.008 (2)	0.012 (2)	0.002 (2)
C6	0.029 (3)	0.024 (2)	0.047 (3)	0.002 (2)	0.014 (2)	0.001 (2)
C7	0.031 (3)	0.025 (2)	0.056 (3)	0.001 (2)	0.019 (2)	0.002 (2)
C8	0.027 (3)	0.030 (2)	0.037 (3)	0.005 (2)	0.013 (2)	0.003 (2)
C9	0.034 (3)	0.028 (3)	0.063 (4)	−0.005 (2)	0.017 (3)	−0.004 (3)
C10	0.031 (3)	0.047 (3)	0.083 (5)	−0.009 (3)	0.019 (3)	0.005 (3)
C11	0.035 (3)	0.034 (3)	0.075 (4)	0.006 (2)	0.021 (3)	−0.009 (3)
C12	0.029 (3)	0.028 (3)	0.073 (4)	0.000 (2)	0.017 (3)	−0.003 (3)
O1	0.0282 (19)	0.0250 (16)	0.049 (2)	−0.0004 (14)	0.0150 (15)	−0.0096 (15)
O2	0.0237 (18)	0.0259 (16)	0.0371 (19)	−0.0067 (14)	0.0060 (14)	−0.0072 (14)
O3	0.044 (2)	0.0207 (17)	0.086 (3)	0.0039 (16)	0.038 (2)	0.0031 (17)
O4	0.039 (2)	0.0222 (17)	0.083 (3)	0.0019 (15)	0.036 (2)	0.0050 (17)
O5	0.050 (2)	0.0264 (16)	0.0346 (19)	−0.0114 (16)	−0.0101 (16)	0.0089 (15)
O6	0.053 (3)	0.0338 (18)	0.033 (2)	−0.0138 (17)	−0.0029 (16)	0.0100 (15)
N1	0.026 (3)	0.048 (3)	0.054 (3)	−0.004 (2)	0.014 (2)	0.002 (2)
N2	0.028 (3)	0.046 (3)	0.067 (3)	0.011 (2)	0.017 (2)	0.003 (2)
O1W	0.065 (3)	0.0229 (17)	0.037 (2)	0.0084 (18)	0.0223 (19)	0.0043 (15)
C13	0.035 (3)	0.030 (2)	0.026 (3)	−0.005 (2)	0.001 (2)	0.001 (2)
C14	0.047 (6)	0.048 (6)	0.048 (6)	−0.008 (5)	−0.007 (5)	0.003 (4)
C14'	0.047 (6)	0.048 (6)	0.048 (6)	−0.008 (5)	−0.007 (5)	0.003 (4)
Cl1	0.0610 (11)	0.0449 (8)	0.0692 (11)	0.0000 (8)	−0.0030 (8)	−0.0018 (8)
O7	0.097 (11)	0.085 (10)	0.090 (10)	0.023 (8)	0.000 (7)	−0.016 (7)
O8	0.130 (10)	0.104 (8)	0.083 (8)	0.032 (8)	−0.039 (7)	−0.001 (7)
O9	0.129 (10)	0.092 (8)	0.143 (11)	−0.067 (7)	−0.032 (8)	0.025 (7)
O10	0.130 (10)	0.120 (9)	0.125 (10)	0.036 (8)	0.045 (8)	0.001 (7)
Cl1'	0.0610 (11)	0.0449 (8)	0.0692 (11)	0.0000 (8)	−0.0030 (8)	−0.0018 (8)
O7'	0.071 (7)	0.071 (7)	0.100 (8)	0.030 (5)	0.024 (6)	0.043 (6)
O8'	0.065 (6)	0.079 (6)	0.158 (9)	−0.003 (5)	−0.016 (6)	−0.012 (6)
O9'	0.164 (10)	0.131 (8)	0.128 (8)	−0.020 (7)	0.068 (7)	0.039 (7)
O10'	0.127 (9)	0.122 (8)	0.097 (7)	0.022 (7)	−0.017 (6)	−0.058 (6)

Geometric parameters (Å, º)

Sm1—O2	2.345 (3)	C9—C10	1.364 (7)
Sm1—O3	2.352 (3)	C9—H9	0.9300
Sm1—O4^i	2.367 (3)	C10—N2	1.346 (6)
Sm1—O1^ii	2.371 (3)	C10—H10	0.9300
Sm1—O5	2.414 (3)	C11—N2	1.337 (7)
Sm1—O1W	2.440 (3)	C11—C12	1.364 (7)
Sm1—O6^i	2.476 (3)	C11—H11	0.9300
Sm1—O5^i	2.521 (3)	C12—H12	0.9300
Sm1—C13^i	2.892 (5)	O1—Sm1^iv	2.371 (3)
Sm1—Sm1^i	3.9263 (5)	O4—Sm1^i	2.367 (3)
Ag1—N2	2.148 (4)	O5—C13	1.249 (5)
Ag1—N1^iii	2.149 (4)	O5—Sm1^i	2.521 (3)
C1—O1	1.252 (5)	O6—C13	1.262 (5)
C1—O2	1.264 (5)	O6—Sm1^i	2.476 (3)
C1—C2	1.495 (6)	N1—Ag1^v	2.149 (4)
C2—C3	1.375 (6)	O1W—H2W	0.81 (4)
C2—C6	1.375 (6)	O1W—H1W	0.81 (4)
C3—C4	1.382 (7)	C13—C14	1.511 (10)
C3—H3	0.9300	C13—C14'	1.511 (9)
C4—N1	1.341 (6)	C13—Sm1^i	2.892 (5)
C4—H4	0.9300	C14—H14A	0.9600
C5—N1	1.333 (6)	C14—H14B	0.9600
C5—C6	1.373 (6)	C14—H14C	0.9600
C5—H5	0.9300	C14'—H14D	0.9600
C6—H6	0.9300	C14'—H14E	0.9600
C7—O3	1.248 (5)	C14'—H14F	0.9600
C7—O4	1.267 (6)	Cl1—O9	1.357 (9)
C7—C8	1.500 (6)	Cl1—O8	1.391 (9)
C8—C9	1.376 (7)	Cl1—O7	1.417 (10)
C8—C12	1.381 (6)	Cl1—O10	1.464 (9)
O2—Sm1—O3	105.57 (13)	C5—C6—H6	120.4
O2—Sm1—O4^i	90.42 (12)	C2—C6—H6	120.4
O3—Sm1—O4^i	137.99 (11)	O3—C7—O4	125.7 (4)
O2—Sm1—O1^ii	85.29 (11)	O3—C7—C8	116.7 (4)
O3—Sm1—O1^ii	75.00 (10)	O4—C7—C8	117.6 (4)
O4^i—Sm1—O1^ii	146.13 (10)	C9—C8—C12	118.3 (4)
O2—Sm1—O5	77.05 (10)	C9—C8—C7	119.9 (4)
O3—Sm1—O5	71.54 (12)	C12—C8—C7	121.8 (4)
O4^i—Sm1—O5	74.83 (12)	C10—C9—C8	119.9 (5)
O1^ii—Sm1—O5	135.91 (12)	C10—C9—H9	120.1
O2—Sm1—O1W	78.25 (13)	C8—C9—H9	120.1
O3—Sm1—O1W	148.79 (11)	N2—C10—C9	122.1 (5)
O4^i—Sm1—O1W	71.75 (11)	N2—C10—H10	118.9
O1^ii—Sm1—O1W	74.48 (11)	C9—C10—H10	118.9
O5—Sm1—O1W	137.85 (11)	N2—C11—C12	123.4 (5)
O2—Sm1—O6^i	155.64 (10)	N2—C11—H11	118.3
O3—Sm1—O6^i	91.24 (14)	C12—C11—H11	118.3
O4^i—Sm1—O6^i	88.48 (14)	C11—C12—C8	118.8 (5)
O1^ii—Sm1—O6^i	82.17 (11)	C11—C12—H12	120.6
O5—Sm1—O6^i	125.83 (10)	C8—C12—H12	120.6
O1W—Sm1—O6^i	78.31 (12)	C1—O1—Sm1^iv	148.9 (3)
O2—Sm1—O5^i	150.36 (10)	C1—O2—Sm1	137.3 (3)
O3—Sm1—O5^i	73.42 (13)	C7—O3—Sm1	140.5 (3)
O4^i—Sm1—O5^i	73.96 (12)	C7—O4—Sm1^i	134.8 (3)
O1^ii—Sm1—O5^i	121.62 (11)	C13—O5—Sm1	160.4 (3)
O5—Sm1—O5^i	74.62 (12)	C13—O5—Sm1^i	94.0 (3)
O1W—Sm1—O5^i	118.44 (13)	Sm1—O5—Sm1^i	105.38 (12)
O6^i—Sm1—O5^i	51.22 (10)	C13—O6—Sm1^i	95.9 (3)
O2—Sm1—C13^i	169.71 (12)	C5—N1—C4	117.6 (4)
O3—Sm1—C13^i	82.55 (14)	C5—N1—Ag1^v	123.2 (3)
O4^i—Sm1—C13^i	79.29 (14)	C4—N1—Ag1^v	119.2 (3)
O1^ii—Sm1—C13^i	103.16 (12)	C11—N2—C10	117.5 (4)
O5—Sm1—C13^i	100.12 (12)	C11—N2—Ag1	126.6 (4)
O1W—Sm1—C13^i	98.16 (14)	C10—N2—Ag1	115.6 (4)
O6^i—Sm1—C13^i	25.73 (11)	Sm1—O1W—H2W	127 (3)
O5^i—Sm1—C13^i	25.53 (11)	Sm1—O1W—H1W	121 (3)
O2—Sm1—Sm1^i	114.86 (7)	H2W—O1W—H1W	106 (4)
O3—Sm1—Sm1^i	67.80 (8)	O5—C13—O6	118.7 (4)
O4^i—Sm1—Sm1^i	70.22 (7)	O5—C13—C14	119.1 (11)
O1^ii—Sm1—Sm1^i	141.10 (7)	O6—C13—C14	121.0 (11)
O5—Sm1—Sm1^i	38.26 (8)	O5—C13—C14'	120.4 (10)
O1W—Sm1—Sm1^i	139.62 (10)	O6—C13—C14'	120.5 (10)
O6^i—Sm1—Sm1^i	87.58 (7)	C14—C13—C14'	16.7 (16)
O5^i—Sm1—Sm1^i	36.36 (7)	O5—C13—Sm1^i	60.4 (2)
C13^i—Sm1—Sm1^i	61.87 (9)	O6—C13—Sm1^i	58.4 (2)
N2—Ag1—N1^iii	166.24 (17)	C14—C13—Sm1^i	165.6 (14)
O1—C1—O2	123.7 (4)	C14'—C13—Sm1^i	177.6 (12)
O1—C1—C2	118.2 (4)	C13—C14—H14A	109.5
O2—C1—C2	118.1 (4)	C13—C14—H14B	109.5
C3—C2—C6	118.2 (4)	C13—C14—H14C	109.5
C3—C2—C1	120.0 (4)	C13—C14'—H14D	109.5
C6—C2—C1	121.8 (4)	C13—C14'—H14E	109.5
C2—C3—C4	119.6 (4)	H14D—C14'—H14E	109.5
C2—C3—H3	120.2	C13—C14'—H14F	109.5
C4—C3—H3	120.2	H14D—C14'—H14F	109.5
N1—C4—C3	122.2 (5)	H14E—C14'—H14F	109.5
N1—C4—H4	118.9	O9—Cl1—O8	112.8 (7)
C3—C4—H4	118.9	O9—Cl1—O7	113.0 (9)
N1—C5—C6	123.2 (4)	O8—Cl1—O7	108.0 (8)
N1—C5—H5	118.4	O9—Cl1—O10	110.1 (8)
C6—C5—H5	118.4	O8—Cl1—O10	106.2 (8)
C5—C6—C2	119.3 (4)	O7—Cl1—O10	106.5 (8)

Symmetry codes: (i) −x+2, −y+2, −z+2; (ii) x, −y+3/2, z+1/2; (iii) −x+1, y+1/2, −z+5/2; (iv) x, −y+3/2, z−1/2; (v) −x+1, y−1/2, −z+5/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W···O6^vi	0.81 (4)	1.98 (4)	2.785 (4)	171 (6)
O1W—H1W···O2^ii	0.81 (4)	2.22 (3)	2.921 (5)	146 (5)

Symmetry codes: (ii) x, −y+3/2, z+1/2; (vi) −x+2, y−1/2, −z+3/2.