Hexa-kis-(μ3-2-hy-droxy-naphthalene-1-carboxaldehyde thio-semicarbazonato-κ(3) N (2):S:S)hexa-silver(I) N,N-dimethyl-formamide tetra-solvate.

In the title compound, [Ag6(C12H10N3OS)6]·4C3H7NO, the hexa-nuclear complex mol-ecule lies about an inversion center. The six Ag atoms form a distorted octa-hedron, with Ag⋯Ag distances in the range 2.933 (1)-3.401 (1) Å. Each Ag atom is surrounded by one N atom and two thiol-ate S atoms from two deprotonated 2-hy-droxy-1-naphthaldehyde thio-semi-carb-a-zone ligands. Each ligand coordinates three Ag atoms via a bridging thiol-ate S atom and a monodentate N atom, thus two Ag3S3 hexa-gonal rings are linked together. Two dimethyl-formamide solvent mol-ecules are located in four sets of sites with half-occupancy and form O⋯H-N hydrogen bonds to the complex mol-ecule. Intra-molecular O-H⋯N hydrogen bonds are also present. The discrete hexa-nuclear clusters are further linked through π-π inter-actions into layers parallel to (001), the shortest distance between the centroids of aromatic rings being 3.698 (2) Å.

Related literature

For the structure and luminescent properties of d 10 metal complexes, see: Brito et al. (2011 ▶); Forward et al. (1995 ▶). For structures of related compexes with thio­semicarbazone Schiff base ligands, see: Ashfield et al. (2004 ▶); Castiñeiras & Pedrido (2009 ▶); Li et al. (2010 ▶); Onodera et al. (2007 ▶); Pedrido et al. (2009 ▶); Sun (2011 ▶); Sun et al. (2012 ▶); Sun & Chai (2012 ▶); Xu et al. (2011 ▶). For bond-length data, see: Han et al. (2004 ▶).

Experimental

Crystal data

[Ag6(C12H10N3OS)6]·4C3H7NO

M = 2405.34

Monoclinic,

a = 24.604 (3) Å

b = 18.877 (3) Å

c = 24.816 (3) Å

β = 94.763 (3)°

V = 11486 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.17 mm−1

T = 293 K

0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.238, T max = 0.373

28454 measured reflections

10056 independent reflections

7829 reflections with I > 2s(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.145

S = 1.08

10056 reflections

667 parameters

63 restraints

H-atom parameters constrained

Δρmax = 0.92 e Å−3

Δρmin = −0.42 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812050155/yk2079sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050155/yk2079Isup2.hkl

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

[Ag6(C12H10N3OS)6]·4C3H7NO	F(000) = 4816
Mr = 2405.34	Dx = 1.391 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6309 reflections
a = 24.604 (3) Å	θ = 2.2–27.2°
b = 18.877 (3) Å	µ = 1.17 mm−1
c = 24.816 (3) Å	T = 293 K
β = 94.763 (3)°	Block, yellow
V = 11486 (3) Å3	0.22 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD diffractometer	10056 independent reflections
Radiation source: fine-focus sealed tube	7829 reflections with I > 2s(I)
Graphite monochromator	Rint = 0.042
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −28→29
Tmin = 0.238, Tmax = 0.373	k = −22→21
28454 measured reflections	l = −29→16

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.095P)2] where P = (Fo2 + 2Fc2)/3
10056 reflections	(Δ/σ)max = 0.002
667 parameters	Δρmax = 0.92 e Å−3
63 restraints	Δρmin = −0.42 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ag1	0.171626 (12)	0.813538 (16)	0.482106 (12)	0.05265 (8)
Ag2	0.240712 (12)	0.788788 (17)	0.582419 (12)	0.05635 (9)
Ag3	0.191030 (13)	0.661685 (16)	0.509778 (12)	0.05414 (8)
S1	0.16540 (4)	0.75257 (5)	0.39220 (4)	0.0510 (2)
S2	0.16228 (4)	0.70906 (5)	0.59592 (4)	0.0520 (2)
S3	0.27035 (4)	0.57841 (5)	0.51287 (4)	0.0499 (2)
N1	0.09822 (14)	0.57526 (18)	0.43441 (14)	0.0591 (9)
N2	0.13114 (13)	0.63483 (17)	0.43751 (13)	0.0531 (8)
N3	0.08875 (19)	0.6661 (3)	0.35352 (18)	0.0993 (14)
H3A	0.0673	0.6301	0.3527	0.119*
H3B	0.0868	0.6956	0.3271	0.119*
N4	0.05033 (12)	0.83205 (16)	0.52337 (13)	0.0475 (8)
N5	0.10008 (12)	0.79779 (16)	0.53377 (12)	0.0476 (8)
N6	0.06729 (14)	0.76102 (19)	0.61488 (13)	0.0614 (9)
H6A	0.0380	0.7858	0.6092	0.074*
H6B	0.0725	0.7360	0.6438	0.074*
N7	0.27039 (15)	0.5619 (2)	0.35485 (14)	0.0656 (10)
N8	0.27440 (14)	0.59230 (18)	0.40692 (12)	0.0575 (9)
N9	0.25925 (15)	0.47922 (19)	0.43895 (15)	0.0671 (10)
H9A	0.2586	0.4610	0.4071	0.080*
H9B	0.2547	0.4527	0.4664	0.080*
O1	0.02497 (15)	0.48899 (18)	0.39190 (13)	0.0853 (10)
H1B	0.0463	0.5224	0.3930	0.128*
O2	−0.05009 (11)	0.86290 (17)	0.53609 (12)	0.0686 (8)
H2B	−0.0209	0.8420	0.5413	0.103*
O3	0.2174 (2)	0.4973 (3)	0.27494 (18)	0.1230 (16)
H3C	0.2245	0.5096	0.3064	0.184*
C1	0.0316 (2)	0.4524 (2)	0.4389 (2)	0.0696 (12)
C2	−0.0022 (2)	0.3926 (3)	0.4433 (2)	0.0858 (16)
H2A	−0.0264	0.3788	0.4144	0.103*
C3	0.0012 (2)	0.3550 (3)	0.4907 (2)	0.0824 (15)
H3D	−0.0213	0.3157	0.4936	0.099*
C4	0.0369 (2)	0.3736 (2)	0.5340 (2)	0.0710 (13)
C5	0.0388 (3)	0.3357 (3)	0.5855 (3)	0.0961 (18)
H5A	0.0155	0.2975	0.5892	0.115*
C6	0.0736 (3)	0.3551 (3)	0.6272 (3)	0.109 (2)
H6C	0.0739	0.3303	0.6596	0.131*
C7	0.1083 (3)	0.4100 (3)	0.6233 (2)	0.104 (2)
H7B	0.1324	0.4220	0.6527	0.125*
C8	0.1084 (2)	0.4484 (3)	0.5761 (2)	0.0873 (16)
H8B	0.1330	0.4856	0.5742	0.105*
C9	0.07184 (19)	0.4329 (2)	0.53019 (19)	0.0678 (12)
C10	0.06846 (18)	0.4728 (2)	0.48118 (18)	0.0633 (11)
C11	0.10170 (17)	0.5363 (2)	0.47600 (18)	0.0600 (11)
H11A	0.1266	0.5487	0.5047	0.072*
C12	0.12505 (16)	0.6761 (2)	0.39585 (16)	0.0529 (10)
C13	−0.04809 (15)	0.9071 (2)	0.49380 (17)	0.0547 (10)
C14	−0.09473 (17)	0.9478 (2)	0.47924 (19)	0.0659 (12)
H14A	−0.1254	0.9428	0.4984	0.079*
C15	−0.09576 (17)	0.9941 (3)	0.4380 (2)	0.0671 (12)
H15A	−0.1271	1.0207	0.4294	0.080*
C16	−0.05039 (17)	1.0030 (2)	0.40773 (17)	0.0602 (11)
C17	−0.0514 (2)	1.0516 (3)	0.36387 (19)	0.0711 (13)
H17A	−0.0823	1.0790	0.3556	0.085*
C18	−0.0087 (2)	1.0587 (3)	0.3344 (2)	0.0818 (15)
H18A	−0.0103	1.0906	0.3058	0.098*
C19	0.0376 (2)	1.0188 (3)	0.3463 (2)	0.0780 (14)
H19A	0.0667	1.0235	0.3249	0.094*
C20	0.04169 (19)	0.9720 (2)	0.38905 (18)	0.0654 (12)
H20A	0.0739	0.9468	0.3968	0.078*
C21	−0.00225 (15)	0.9620 (2)	0.42120 (16)	0.0521 (10)
C22	−0.00177 (15)	0.9137 (2)	0.46551 (15)	0.0497 (9)
C23	0.04720 (15)	0.87334 (19)	0.48270 (15)	0.0484 (9)
H23A	0.0776	0.8780	0.4630	0.058*
C24	0.10444 (14)	0.76144 (19)	0.57889 (14)	0.0435 (8)
C25	0.2510 (3)	0.5314 (4)	0.2427 (2)	0.104 (2)
C26	0.2459 (3)	0.5160 (4)	0.1857 (3)	0.1147 (18)
H26A	0.2203	0.4836	0.1712	0.138*
C27	0.2789 (3)	0.5496 (4)	0.1544 (3)	0.1144 (18)
H27A	0.2745	0.5391	0.1177	0.137*
C28	0.3180 (3)	0.5973 (3)	0.1699 (2)	0.0934 (15)
C29	0.3531 (3)	0.6318 (4)	0.1345 (2)	0.1046 (18)
H29A	0.3493	0.6213	0.0977	0.126*
C30	0.3886 (3)	0.6755 (4)	0.1515 (3)	0.127 (2)
H30A	0.4086	0.6988	0.1268	0.152*
C31	0.3996 (3)	0.6910 (4)	0.2081 (3)	0.114 (2)
H31A	0.4273	0.7223	0.2199	0.137*
C32	0.3687 (3)	0.6590 (3)	0.2442 (2)	0.1015 (19)
H32A	0.3757	0.6680	0.2809	0.122*
C33	0.3264 (2)	0.6125 (3)	0.2266 (2)	0.0911 (16)
C34	0.2898 (2)	0.5779 (3)	0.26316 (19)	0.0814 (15)
C35	0.29397 (18)	0.5973 (3)	0.32006 (16)	0.0645 (12)
H35A	0.3145	0.6368	0.3313	0.077*
C36	0.26717 (15)	0.5477 (2)	0.44566 (15)	0.0488 (9)
C37	0.1231 (5)	0.9297 (5)	0.2325 (5)	0.087 (3)	0.50
H37A	0.1419	0.9325	0.2679	0.130*	0.50
H37B	0.0973	0.9678	0.2277	0.130*	0.50
H37C	0.1489	0.9331	0.2056	0.130*	0.50
C38	0.0619 (5)	0.8437 (6)	0.1746 (5)	0.089 (3)	0.50
H38A	0.0455	0.7980	0.1785	0.133*	0.50
H38B	0.0854	0.8423	0.1456	0.133*	0.50
H38C	0.0338	0.8784	0.1667	0.133*	0.50
C39	0.0960 (4)	0.8193 (6)	0.2672 (4)	0.078 (3)	0.50
H39A	0.1113	0.8342	0.3008	0.093*	0.50
N10	0.0949 (3)	0.8634 (3)	0.2267 (3)	0.0561 (17)	0.50
O4	0.0773 (3)	0.7578 (4)	0.2628 (3)	0.095 (2)	0.50
C40	0.2559 (5)	0.7879 (6)	0.2711 (4)	0.087 (3)	0.50
H40A	0.2754	0.8308	0.2806	0.130*	0.50
H40B	0.2801	0.7482	0.2767	0.130*	0.50
H40C	0.2260	0.7828	0.2932	0.130*	0.50
C41	0.2129 (6)	0.7401 (7)	0.2012 (6)	0.161 (6)	0.50
H41A	0.2007	0.7454	0.1636	0.242*	0.50
H41B	0.1820	0.7328	0.2217	0.242*	0.50
H41C	0.2369	0.7001	0.2057	0.242*	0.50
C42	0.2428 (7)	0.8450 (8)	0.1807 (6)	0.125 (5)	0.50
H42A	0.2656	0.8799	0.1965	0.150*	0.50
N11	0.2359 (3)	0.7908 (4)	0.2164 (3)	0.0563 (18)	0.50
O5	0.2296 (5)	0.8580 (5)	0.1406 (3)	0.136 (4)	0.50
O6	0.4334 (3)	0.8328 (4)	0.2955 (3)	0.090 (2)	0.50
C43	0.4240 (4)	1.0056 (5)	0.2406 (4)	0.081 (3)	0.50
H43A	0.4350	1.0254	0.2754	0.121*	0.50
H43B	0.3889	1.0239	0.2279	0.121*	0.50
H43C	0.4502	1.0180	0.2155	0.121*	0.50
C44	0.4052 (4)	0.8921 (6)	0.1971 (4)	0.084 (3)	0.50
H44A	0.4048	0.8424	0.2051	0.126*	0.50
H44B	0.4307	0.9012	0.1707	0.126*	0.50
H44C	0.3694	0.9069	0.1832	0.126*	0.50
C45	0.4319 (4)	0.8969 (7)	0.2912 (5)	0.089 (3)	0.50
H45A	0.4389	0.9239	0.3224	0.107*	0.50
N12	0.4210 (3)	0.9304 (4)	0.2449 (2)	0.063 (2)	0.50
O7	0.2454 (2)	0.3792 (3)	0.5239 (2)	0.0587 (13)	0.50
C46	0.1547 (4)	0.2320 (4)	0.5242 (4)	0.075 (3)	0.50
H46A	0.1703	0.2201	0.5598	0.112*	0.50
H46B	0.1600	0.1934	0.5000	0.112*	0.50
H46C	0.1164	0.2410	0.5252	0.112*	0.50
C47	0.1648 (4)	0.3228 (5)	0.4527 (4)	0.073 (3)	0.50
H47A	0.1858	0.3643	0.4461	0.109*	0.50
H47B	0.1268	0.3351	0.4510	0.109*	0.50
H47C	0.1704	0.2876	0.4259	0.109*	0.50
C48	0.2207 (4)	0.3293 (4)	0.5356 (3)	0.060 (2)	0.50
H48A	0.2294	0.3111	0.5701	0.072*	0.50
N13	0.1815 (3)	0.2954 (3)	0.5052 (3)	0.0468 (15)	0.50

	U11	U22	U33	U12	U13	U23
Ag1	0.05776 (17)	0.05486 (17)	0.04597 (16)	−0.00022 (13)	0.00805 (13)	0.00734 (12)
Ag2	0.05578 (17)	0.06027 (18)	0.05285 (18)	0.00050 (13)	0.00367 (14)	0.00891 (13)
Ag3	0.06226 (18)	0.05244 (17)	0.04791 (17)	0.00372 (13)	0.00561 (14)	0.00294 (12)
S1	0.0549 (5)	0.0543 (5)	0.0438 (5)	−0.0023 (4)	0.0035 (4)	0.0061 (4)
S2	0.0564 (5)	0.0552 (5)	0.0450 (5)	0.0023 (4)	0.0079 (4)	0.0091 (4)
S3	0.0570 (5)	0.0488 (5)	0.0446 (5)	0.0013 (4)	0.0081 (4)	0.0031 (4)
N1	0.0648 (19)	0.0566 (19)	0.0556 (19)	−0.0095 (16)	0.0042 (16)	0.0038 (16)
N2	0.0554 (17)	0.0538 (18)	0.0497 (18)	−0.0064 (15)	0.0017 (14)	0.0065 (15)
N3	0.109 (3)	0.098 (3)	0.085 (3)	−0.033 (2)	−0.027 (2)	0.016 (2)
N4	0.0439 (15)	0.0487 (17)	0.0504 (17)	0.0009 (13)	0.0069 (13)	0.0001 (14)
N5	0.0439 (15)	0.0514 (17)	0.0480 (17)	0.0004 (13)	0.0064 (13)	0.0060 (13)
N6	0.0601 (19)	0.073 (2)	0.0532 (19)	0.0072 (17)	0.0165 (16)	0.0100 (16)
N7	0.079 (2)	0.068 (2)	0.0490 (19)	0.0157 (18)	0.0009 (17)	−0.0046 (17)
N8	0.071 (2)	0.063 (2)	0.0390 (17)	0.0076 (17)	0.0063 (15)	0.0032 (15)
N9	0.091 (3)	0.057 (2)	0.054 (2)	−0.0044 (18)	0.0069 (18)	−0.0029 (16)
O1	0.116 (3)	0.073 (2)	0.0638 (19)	−0.0227 (19)	−0.0104 (18)	−0.0023 (16)
O2	0.0522 (15)	0.084 (2)	0.0713 (19)	0.0015 (15)	0.0128 (14)	0.0191 (16)
O3	0.131 (3)	0.137 (4)	0.095 (3)	−0.006 (3)	−0.029 (3)	−0.024 (3)
C1	0.082 (3)	0.057 (2)	0.070 (3)	−0.012 (2)	0.007 (2)	−0.005 (2)
C2	0.105 (4)	0.064 (3)	0.086 (4)	−0.028 (3)	−0.005 (3)	−0.007 (3)
C3	0.093 (3)	0.056 (3)	0.099 (4)	−0.024 (2)	0.011 (3)	−0.001 (3)
C4	0.081 (3)	0.053 (2)	0.080 (3)	−0.011 (2)	0.012 (2)	0.006 (2)
C5	0.110 (4)	0.067 (3)	0.112 (5)	−0.018 (3)	0.013 (4)	0.020 (3)
C6	0.135 (5)	0.097 (4)	0.095 (4)	−0.015 (4)	0.008 (4)	0.041 (3)
C7	0.127 (5)	0.093 (4)	0.088 (4)	−0.028 (4)	−0.022 (3)	0.032 (3)
C8	0.093 (3)	0.075 (3)	0.091 (4)	−0.023 (3)	−0.010 (3)	0.019 (3)
C9	0.073 (3)	0.056 (2)	0.075 (3)	−0.005 (2)	0.004 (2)	0.007 (2)
C10	0.073 (3)	0.054 (2)	0.063 (3)	−0.012 (2)	0.008 (2)	0.0020 (19)
C11	0.063 (2)	0.057 (2)	0.059 (2)	−0.0090 (19)	0.000 (2)	−0.001 (2)
C12	0.057 (2)	0.053 (2)	0.047 (2)	−0.0052 (17)	−0.0048 (17)	0.0039 (17)
C13	0.048 (2)	0.057 (2)	0.058 (2)	−0.0037 (18)	0.0050 (18)	−0.0016 (18)
C14	0.047 (2)	0.071 (3)	0.080 (3)	0.001 (2)	0.010 (2)	−0.001 (2)
C15	0.050 (2)	0.069 (3)	0.081 (3)	0.011 (2)	−0.001 (2)	−0.007 (2)
C16	0.064 (2)	0.052 (2)	0.061 (2)	0.0017 (19)	−0.011 (2)	−0.0077 (19)
C17	0.075 (3)	0.064 (3)	0.072 (3)	0.004 (2)	−0.011 (2)	0.008 (2)
C18	0.106 (4)	0.068 (3)	0.069 (3)	0.001 (3)	−0.005 (3)	0.019 (2)
C19	0.091 (3)	0.079 (3)	0.064 (3)	−0.003 (3)	0.013 (3)	0.013 (2)
C20	0.070 (3)	0.067 (3)	0.060 (3)	0.003 (2)	0.012 (2)	0.006 (2)
C21	0.054 (2)	0.048 (2)	0.053 (2)	−0.0029 (17)	0.0006 (17)	−0.0022 (17)
C22	0.050 (2)	0.048 (2)	0.050 (2)	−0.0012 (16)	−0.0007 (16)	−0.0053 (16)
C23	0.0459 (18)	0.047 (2)	0.053 (2)	0.0008 (16)	0.0070 (16)	−0.0009 (17)
C24	0.0447 (17)	0.0476 (19)	0.0386 (18)	−0.0071 (15)	0.0062 (15)	−0.0008 (15)
C25	0.123 (5)	0.123 (5)	0.060 (3)	0.036 (4)	−0.021 (3)	−0.018 (3)
C26	0.119 (3)	0.127 (5)	0.093 (4)	0.025 (3)	−0.021 (2)	−0.002 (3)
C27	0.131 (3)	0.117 (3)	0.093 (3)	0.036 (3)	−0.002 (2)	−0.010 (3)
C28	0.109 (3)	0.105 (3)	0.0665 (12)	0.033 (3)	0.009 (2)	0.005 (2)
C29	0.126 (3)	0.119 (3)	0.072 (3)	0.026 (3)	0.022 (3)	0.007 (3)
C30	0.137 (4)	0.138 (4)	0.109 (4)	0.021 (3)	0.032 (3)	0.022 (3)
C31	0.123 (4)	0.118 (4)	0.103 (3)	0.020 (3)	0.025 (3)	0.017 (3)
C32	0.126 (4)	0.108 (4)	0.076 (3)	0.045 (4)	0.043 (3)	0.030 (3)
C33	0.116 (4)	0.105 (4)	0.0553 (15)	0.061 (3)	0.026 (2)	0.022 (2)
C34	0.105 (3)	0.088 (3)	0.050 (3)	0.045 (3)	0.000 (2)	0.002 (2)
C35	0.080 (3)	0.072 (3)	0.042 (2)	0.021 (2)	0.006 (2)	0.0029 (19)
C36	0.0509 (19)	0.048 (2)	0.047 (2)	0.0081 (16)	0.0000 (16)	−0.0023 (16)
C37	0.098 (7)	0.069 (6)	0.091 (7)	−0.002 (5)	−0.009 (6)	0.005 (5)
C38	0.104 (4)	0.079 (4)	0.081 (4)	0.007 (3)	−0.013 (4)	0.012 (3)
C39	0.091 (7)	0.082 (6)	0.056 (5)	0.006 (5)	−0.024 (5)	0.014 (5)
N10	0.071 (4)	0.037 (3)	0.057 (4)	0.015 (3)	−0.020 (3)	0.011 (3)
O4	0.105 (4)	0.095 (4)	0.078 (3)	−0.016 (3)	−0.027 (3)	0.037 (3)
C40	0.116 (8)	0.080 (7)	0.063 (6)	0.031 (6)	−0.002 (6)	−0.007 (5)
C41	0.162 (12)	0.139 (11)	0.189 (15)	0.098 (9)	0.052 (11)	0.082 (10)
C42	0.157 (12)	0.105 (10)	0.112 (11)	−0.033 (9)	0.004 (10)	−0.007 (8)
N11	0.079 (4)	0.050 (4)	0.041 (3)	0.008 (3)	0.015 (3)	0.004 (3)
O5	0.222 (10)	0.130 (6)	0.054 (4)	−0.029 (7)	−0.002 (5)	0.058 (4)
O6	0.115 (5)	0.103 (5)	0.055 (3)	0.005 (4)	0.030 (3)	0.049 (3)
C43	0.086 (6)	0.071 (6)	0.084 (7)	−0.016 (5)	−0.003 (5)	0.017 (5)
C44	0.092 (7)	0.084 (7)	0.076 (6)	−0.011 (5)	0.004 (5)	0.033 (5)
C45	0.082 (4)	0.104 (5)	0.082 (4)	0.000 (4)	0.014 (3)	0.004 (4)
N12	0.049 (3)	0.103 (5)	0.038 (3)	0.001 (4)	0.000 (3)	0.029 (3)
O7	0.086 (3)	0.049 (2)	0.038 (2)	−0.033 (2)	−0.010 (2)	0.0095 (19)
C46	0.081 (6)	0.048 (5)	0.096 (7)	−0.031 (4)	0.010 (5)	0.001 (5)
C47	0.078 (6)	0.060 (5)	0.076 (6)	−0.007 (4)	−0.024 (5)	−0.009 (4)
C48	0.101 (6)	0.051 (4)	0.025 (3)	−0.008 (4)	−0.005 (4)	0.007 (3)
N13	0.058 (3)	0.031 (3)	0.050 (4)	−0.010 (3)	0.002 (3)	−0.009 (2)

Ag1—N5	2.282 (3)	C18—C19	1.377 (7)
Ag1—S3i	2.4869 (10)	C18—H18A	0.9300
Ag1—S1	2.5039 (10)	C19—C20	1.378 (6)
Ag1—Ag2	2.9329 (5)	C19—H19A	0.9300
Ag1—Ag3	2.9769 (6)	C20—C21	1.409 (6)
Ag2—N8i	2.294 (3)	C20—H20A	0.9300
Ag2—S1i	2.4699 (10)	C21—C22	1.428 (5)
Ag2—S2	2.4917 (11)	C22—C23	1.459 (5)
Ag2—Ag3i	3.0931 (5)	C23—H23A	0.9300
Ag2—Ag3	3.1835 (5)	C25—C34	1.364 (8)
Ag3—N2	2.282 (3)	C25—C26	1.438 (8)
Ag3—S2	2.4741 (11)	C26—C27	1.330 (10)
Ag3—S3	2.5020 (10)	C26—H26A	0.9300
Ag3—Ag2i	3.0931 (5)	C27—C28	1.350 (9)
S1—C12	1.759 (4)	C27—H27A	0.9300
S1—Ag2i	2.4699 (10)	C28—C33	1.436 (7)
S2—C24	1.755 (4)	C28—C29	1.438 (9)
S3—C36	1.762 (4)	C29—C30	1.248 (10)
S3—Ag1i	2.4869 (10)	C29—H29A	0.9300
N1—C11	1.264 (5)	C30—C31	1.438 (10)
N1—N2	1.384 (5)	C30—H30A	0.9300
N2—C12	1.293 (5)	C31—C32	1.363 (9)
N3—C12	1.335 (6)	C31—H31A	0.9300
N3—H3A	0.8600	C32—C33	1.403 (9)
N3—H3B	0.8600	C32—H32A	0.9300
N4—C23	1.273 (5)	C33—C34	1.480 (8)
N4—N5	1.390 (4)	C34—C35	1.454 (6)
N5—C24	1.310 (5)	C35—H35A	0.9300
N6—C24	1.330 (5)	C37—N10	1.432 (12)
N6—H6A	0.8600	C37—H37A	0.9600
N6—H6B	0.8600	C37—H37B	0.9600
N7—C35	1.270 (6)	C37—H37C	0.9600
N7—N8	1.410 (5)	C38—N10	1.516 (12)
N8—C36	1.302 (5)	C38—H38A	0.9600
N8—Ag2i	2.294 (3)	C38—H38B	0.9600
N9—C36	1.315 (5)	C38—H38C	0.9600
N9—H9A	0.8600	C39—O4	1.250 (12)
N9—H9B	0.8600	C39—N10	1.302 (11)
O1—C1	1.354 (6)	C39—H39A	0.9300
O1—H1B	0.8200	C40—N11	1.406 (11)
O2—C13	1.345 (5)	C40—H40A	0.9600
O2—H2B	0.8200	C40—H40B	0.9600
O3—C25	1.361 (8)	C40—H40C	0.9600
O3—H3C	0.8200	C41—N11	1.159 (16)
C1—C10	1.384 (6)	C41—H41A	0.9600
C1—C2	1.411 (7)	C41—H41B	0.9600
C2—C3	1.369 (7)	C41—H41C	0.9600
C2—H2A	0.9300	C42—O5	1.052 (16)
C3—C4	1.377 (7)	C42—N11	1.372 (16)
C3—H3D	0.9300	C42—H42A	0.9300
C4—C9	1.419 (6)	O6—C45	1.215 (14)
C4—C5	1.461 (8)	C43—N12	1.425 (13)
C5—C6	1.340 (9)	C43—H43A	0.9600
C5—H5A	0.9300	C43—H43B	0.9600
C6—C7	1.352 (8)	C43—H43C	0.9600
C6—H6C	0.9300	C44—N12	1.415 (13)
C7—C8	1.377 (8)	C44—H44A	0.9600
C7—H7B	0.9300	C44—H44B	0.9600
C8—C9	1.422 (7)	C44—H44C	0.9600
C8—H8B	0.9300	C45—N12	1.320 (13)
C9—C10	1.428 (6)	C45—H45A	0.9300
C10—C11	1.463 (6)	O7—C48	1.171 (10)
C11—H11A	0.9300	C46—N13	1.463 (10)
C13—C22	1.393 (5)	C46—H46A	0.9600
C13—C14	1.404 (6)	C46—H46B	0.9600
C14—C15	1.343 (7)	C46—H46C	0.9600
C14—H14A	0.9300	C47—N13	1.428 (11)
C15—C16	1.407 (6)	C47—H47A	0.9600
C15—H15A	0.9300	C47—H47B	0.9600
C16—C17	1.423 (6)	C47—H47C	0.9600
C16—C21	1.431 (6)	C48—N13	1.338 (10)
C17—C18	1.334 (7)	C48—H48A	0.9300
C17—H17A	0.9300
N5—Ag1—S3i	123.04 (8)	C18—C19—C20	121.5 (5)
N5—Ag1—S1	116.61 (8)	C18—C19—H19A	119.3
S3i—Ag1—S1	114.45 (3)	C20—C19—H19A	119.3
N5—Ag1—Ag2	85.53 (8)	C19—C20—C21	120.8 (4)
S3i—Ag1—Ag2	78.36 (2)	C19—C20—H20A	119.6
S1—Ag1—Ag2	132.17 (3)	C21—C20—H20A	119.6
N5—Ag1—Ag3	82.03 (8)	C20—C21—C22	124.4 (4)
S3i—Ag1—Ag3	134.25 (3)	C20—C21—C16	117.0 (4)
S1—Ag1—Ag3	76.10 (2)	C22—C21—C16	118.6 (4)
Ag2—Ag1—Ag3	65.183 (11)	C13—C22—C21	119.4 (3)
N8i—Ag2—S1i	115.91 (9)	C13—C22—C23	119.8 (3)
N8i—Ag2—S2	116.15 (9)	C21—C22—C23	120.8 (3)
S1i—Ag2—S2	119.55 (4)	N4—C23—C22	123.1 (3)
N8i—Ag2—Ag1	81.60 (8)	N4—C23—H23A	118.5
S1i—Ag2—Ag1	136.94 (3)	C22—C23—H23A	118.5
S2—Ag2—Ag1	79.02 (2)	N5—C24—N6	124.4 (3)
N8i—Ag2—Ag3i	83.84 (8)	N5—C24—S2	120.5 (3)
S1i—Ag2—Ag3i	74.37 (2)	N6—C24—S2	115.1 (3)
S2—Ag2—Ag3i	139.12 (3)	O3—C25—C34	121.8 (5)
Ag1—Ag2—Ag3i	68.654 (13)	O3—C25—C26	118.3 (6)
N8i—Ag2—Ag3	138.11 (8)	C34—C25—C26	119.9 (6)
S1i—Ag2—Ag3	102.31 (3)	C27—C26—C25	118.0 (7)
S2—Ag2—Ag3	49.88 (2)	C27—C26—H26A	121.0
Ag1—Ag2—Ag3	58.076 (12)	C25—C26—H26A	121.0
Ag3i—Ag2—Ag3	90.886 (14)	C26—C27—C28	127.3 (7)
N2—Ag3—S2	123.17 (9)	C26—C27—H27A	116.3
N2—Ag3—S3	109.62 (9)	C28—C27—H27A	116.3
S2—Ag3—S3	118.61 (3)	C27—C28—C33	117.0 (6)
N2—Ag3—Ag1	87.24 (8)	C27—C28—C29	125.3 (6)
S2—Ag3—Ag1	78.42 (3)	C33—C28—C29	117.7 (6)
S3—Ag3—Ag1	136.20 (3)	C30—C29—C28	122.0 (7)
N2—Ag3—Ag2i	80.83 (8)	C30—C29—H29A	119.0
S2—Ag3—Ag2i	137.87 (3)	C28—C29—H29A	119.0
S3—Ag3—Ag2i	75.09 (2)	C29—C30—C31	122.4 (8)
Ag1—Ag3—Ag2i	67.966 (11)	C29—C30—H30A	118.8
N2—Ag3—Ag2	143.62 (8)	C31—C30—H30A	118.8
S2—Ag3—Ag2	50.37 (2)	C32—C31—C30	118.7 (7)
S3—Ag3—Ag2	101.20 (3)	C32—C31—H31A	120.7
Ag1—Ag3—Ag2	56.741 (12)	C30—C31—H31A	120.7
Ag2i—Ag3—Ag2	89.114 (14)	C31—C32—C33	120.9 (6)
C12—S1—Ag2i	104.32 (14)	C31—C32—H32A	119.5
C12—S1—Ag1	108.93 (14)	C33—C32—H32A	119.5
Ag2i—S1—Ag1	86.06 (3)	C32—C33—C28	118.1 (5)
C24—S2—Ag3	106.25 (12)	C32—C33—C34	124.0 (5)
C24—S2—Ag2	104.41 (12)	C28—C33—C34	117.9 (6)
Ag3—S2—Ag2	79.74 (3)	C25—C34—C35	121.0 (5)
C36—S3—Ag1i	107.32 (13)	C25—C34—C33	119.8 (5)
C36—S3—Ag3	101.81 (12)	C35—C34—C33	119.1 (5)
Ag1i—S3—Ag3	85.95 (3)	N7—C35—C34	121.9 (5)
C11—N1—N2	115.3 (3)	N7—C35—H35A	119.1
C12—N2—N1	114.6 (3)	C34—C35—H35A	119.1
C12—N2—Ag3	121.3 (3)	N8—C36—N9	124.8 (4)
N1—N2—Ag3	124.1 (2)	N8—C36—S3	119.2 (3)
C12—N3—H3A	120.0	N9—C36—S3	116.0 (3)
C12—N3—H3B	120.0	N10—C37—H37A	109.5
H3A—N3—H3B	120.0	N10—C37—H37B	109.5
C23—N4—N5	115.3 (3)	H37A—C37—H37B	109.5
C24—N5—N4	114.3 (3)	N10—C37—H37C	109.5
C24—N5—Ag1	122.4 (2)	H37A—C37—H37C	109.5
N4—N5—Ag1	122.9 (2)	H37B—C37—H37C	109.5
C24—N6—H6A	120.0	N10—C38—H38A	109.5
C24—N6—H6B	120.0	N10—C38—H38B	109.5
H6A—N6—H6B	120.0	H38A—C38—H38B	109.5
C35—N7—N8	114.1 (4)	N10—C38—H38C	109.5
C36—N8—N7	114.2 (3)	H38A—C38—H38C	109.5
C36—N8—Ag2i	121.0 (3)	H38B—C38—H38C	109.5
N7—N8—Ag2i	120.3 (2)	O4—C39—N10	122.9 (9)
C36—N9—H9A	120.0	O4—C39—H39A	118.5
C36—N9—H9B	120.0	N10—C39—H39A	118.5
H9A—N9—H9B	120.0	C39—N10—C37	120.2 (8)
C1—O1—H1B	109.5	C39—N10—C38	118.4 (8)
C13—O2—H2B	109.5	C37—N10—C38	121.3 (7)
C25—O3—H3C	109.5	N11—C40—H40A	109.5
O1—C1—C10	122.3 (4)	N11—C40—H40B	109.5
O1—C1—C2	116.5 (4)	H40A—C40—H40B	109.5
C10—C1—C2	121.1 (5)	N11—C40—H40C	109.5
C3—C2—C1	119.2 (5)	H40A—C40—H40C	109.5
C3—C2—H2A	120.4	H40B—C40—H40C	109.5
C1—C2—H2A	120.4	N11—C41—H41A	109.5
C2—C3—C4	121.7 (5)	N11—C41—H41B	109.5
C2—C3—H3D	119.1	H41A—C41—H41B	109.5
C4—C3—H3D	119.1	N11—C41—H41C	109.5
C3—C4—C9	120.1 (4)	H41A—C41—H41C	109.5
C3—C4—C5	121.9 (5)	H41B—C41—H41C	109.5
C9—C4—C5	118.0 (5)	O5—C42—N11	137.7 (15)
C6—C5—C4	121.0 (5)	O5—C42—H42A	111.2
C6—C5—H5A	119.5	N11—C42—H42A	111.2
C4—C5—H5A	119.5	C41—N11—C42	119.4 (11)
C5—C6—C7	121.3 (6)	C41—N11—C40	113.8 (10)
C5—C6—H6C	119.3	C42—N11—C40	126.8 (9)
C7—C6—H6C	119.3	N12—C43—H43A	109.5
C6—C7—C8	120.7 (6)	N12—C43—H43B	109.5
C6—C7—H7B	119.6	H43A—C43—H43B	109.5
C8—C7—H7B	119.6	N12—C43—H43C	109.5
C7—C8—C9	121.8 (5)	H43A—C43—H43C	109.5
C7—C8—H8B	119.1	H43B—C43—H43C	109.5
C9—C8—H8B	119.1	N12—C44—H44A	109.5
C4—C9—C8	117.1 (4)	N12—C44—H44B	109.5
C4—C9—C10	118.7 (4)	H44A—C44—H44B	109.5
C8—C9—C10	124.2 (4)	N12—C44—H44C	109.5
C1—C10—C9	119.1 (4)	H44A—C44—H44C	109.5
C1—C10—C11	119.9 (4)	H44B—C44—H44C	109.5
C9—C10—C11	120.9 (4)	O6—C45—N12	123.7 (11)
N1—C11—C10	123.2 (4)	O6—C45—H45A	118.1
N1—C11—H11A	118.4	N12—C45—H45A	118.1
C10—C11—H11A	118.4	C45—N12—C44	120.4 (9)
N2—C12—N3	124.7 (4)	C45—N12—C43	122.3 (9)
N2—C12—S1	120.5 (3)	C44—N12—C43	117.2 (7)
N3—C12—S1	114.8 (3)	N13—C46—H46A	109.5
O2—C13—C22	122.2 (3)	N13—C46—H46B	109.5
O2—C13—C14	117.3 (4)	H46A—C46—H46B	109.5
C22—C13—C14	120.5 (4)	N13—C46—H46C	109.5
C15—C14—C13	121.0 (4)	H46A—C46—H46C	109.5
C15—C14—H14A	119.5	H46B—C46—H46C	109.5
C13—C14—H14A	119.5	N13—C47—H47A	109.5
C14—C15—C16	121.3 (4)	N13—C47—H47B	109.5
C14—C15—H15A	119.4	H47A—C47—H47B	109.5
C16—C15—H15A	119.4	N13—C47—H47C	109.5
C15—C16—C17	121.5 (4)	H47A—C47—H47C	109.5
C15—C16—C21	119.2 (4)	H47B—C47—H47C	109.5
C17—C16—C21	119.3 (4)	O7—C48—N13	127.4 (7)
C18—C17—C16	121.3 (4)	O7—C48—H48A	116.3
C18—C17—H17A	119.3	N13—C48—H48A	116.3
C16—C17—H17A	119.3	C48—N13—C47	118.8 (6)
C17—C18—C19	120.1 (5)	C48—N13—C46	122.1 (7)
C17—C18—H18A	119.9	C47—N13—C46	119.1 (7)
C19—C18—H18A	119.9

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O4	0.86	1.98	2.835 (8)	175
N6—H6B···O6i	0.86	2.00	2.845 (7)	166
N9—H9A···O5ii	0.86	2.31	3.049 (8)	145
N9—H9B···O7	0.86	2.02	2.870 (6)	172
O1—H1B···N1	0.82	1.86	2.588 (5)	147
O2—H2B···N4	0.82	1.85	2.583 (4)	148
O3—H3C···N7	0.82	1.86	2.587 (5)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯O4	0.86	1.98	2.835 (8)	175
N6—H6B⋯O6i	0.86	2.00	2.845 (7)	166
N9—H9A⋯O5ii	0.86	2.31	3.049 (8)	145
N9—H9B⋯O7	0.86	2.02	2.870 (6)	172
O1—H1B⋯N1	0.82	1.86	2.588 (5)	147
O2—H2B⋯N4	0.82	1.85	2.583 (4)	148
O3—H3C⋯N7	0.82	1.86	2.587 (5)	147

Symmetry codes: (i) ; (ii) .