Bis[μ-1,2-bis-(1H-imidazol-1-ylmeth-yl)benzene-κN:N]disilver(I) bis-(4-carb-oxy-naphthalene-1-carboxyl-ate) tetra-hydrate.

In the title compound, [Ag(2)(C(14)H(14)N(4))(2)](C(12)H(7)O(4))(2)·4H(2)O, the dinuclear dication has crystallographically imposed inversion symmetry. Each Ag(I) ion is bicoordinated in a slightly distorted linear coordination geometry by the N atoms of two ligands, resulting in the formation of a 22-membered metallamacrocycle. In the dication, π-π inter-actions are observed between the imidazole rings, with centroid-centroid distances of 3.528 (3) Å and dihedral angles of 9.92 (9)°. The crystal structure is stabilized by inter-molecular O-H⋯O hydrogen bonds and π-π inter-actions involving the benzene rings of adjacent dications, with centroid-centroid distances of 3.651 (2) Å.

Related literature

For the synthesis and structures of related compounds, see: Tan et al. (2004 ▶); Liu et al. (2007 ▶); Liu, Ma et al. (2008 ▶); Liu, Chi & Wang (2008 ▶); Sun et al. (2009 ▶).

Experimental

Crystal data

[Ag2(C14H14N4)2](C12H7O4)2·4H2O

M = 1194.74

Triclinic,

a = 9.6644 (5) Å

b = 11.3769 (12) Å

c = 11.8255 (5) Å

α = 109.376 (8)°

β = 95.783 (3)°

γ = 94.442 (4)°

V = 1211.79 (15) Å3

Z = 1

Mo Kα radiation

μ = 0.88 mm−1

T = 293 K

0.15 × 0.12 × 0.11 mm

Data collection

Bruker APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.35, T max = 0.59

8572 measured reflections

4904 independent reflections

3384 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.069

S = 0.89

4904 reflections

346 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.43 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1999 ▶); 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811018691/rz2589sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018691/rz2589Isup2.hkl

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

[Ag2(C14H14N4)2](C12H7O4)2·4H2O	Z = 1
Mr = 1194.74	F(000) = 608
Triclinic, P1	Dx = 1.637 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6644 (5) Å	Cell parameters from 4904 reflections
b = 11.3769 (12) Å	θ = 1.8–26.4°
c = 11.8255 (5) Å	µ = 0.88 mm−1
α = 109.376 (8)°	T = 293 K
β = 95.783 (3)°	Block, pale yellow
γ = 94.442 (4)°	0.15 × 0.12 × 0.11 mm
V = 1211.79 (15) Å3

Bruker APEX diffractometer	4904 independent reflections
Radiation source: fine-focus sealed tube	3384 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 26.4°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −11→12
Tmin = 0.35, Tmax = 0.59	k = −14→12
8572 measured reflections	l = −14→11

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 0.89	w = 1/[σ2(Fo2) + (0.0385P)2] where P = (Fo2 + 2Fc2)/3
4904 reflections	(Δ/σ)max = 0.001
346 parameters	Δρmax = 0.30 e Å−3
6 restraints	Δρmin = −0.43 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
C1	0.6791 (3)	−0.0550 (2)	0.0091 (2)	0.0501 (6)
H1	0.6710	−0.1140	−0.0684	0.060*
C2	0.6045 (3)	−0.0634 (2)	0.0974 (2)	0.0458 (6)
H2	0.5361	−0.1279	0.0919	0.055*
C3	0.7469 (2)	0.1091 (2)	0.1643 (2)	0.0424 (6)
H3	0.7937	0.1857	0.2157	0.051*
C4	0.5997 (3)	0.0755 (2)	0.3151 (2)	0.0442 (6)
H4A	0.5347	0.1374	0.3205	0.053*
H4B	0.6790	0.1137	0.3774	0.053*
C5	0.5284 (2)	−0.0355 (2)	0.33815 (18)	0.0341 (5)
C6	0.3839 (2)	−0.0568 (2)	0.3188 (2)	0.0434 (6)
H6	0.3335	−0.0034	0.2905	0.052*
C7	0.3121 (2)	−0.1558 (3)	0.3405 (2)	0.0479 (6)
H7	0.2147	−0.1685	0.3266	0.058*
C8	0.3846 (3)	−0.2340 (2)	0.3823 (2)	0.0460 (6)
H8	0.3371	−0.3008	0.3968	0.055*
C9	0.5289 (3)	−0.2138 (2)	0.4032 (2)	0.0420 (6)
H9	0.5780	−0.2673	0.4324	0.050*
C10	0.6025 (2)	−0.1153 (2)	0.38161 (18)	0.0329 (5)
C11	0.7610 (2)	−0.0995 (2)	0.4061 (2)	0.0443 (6)
H11A	0.7950	−0.0110	0.4437	0.053*
H11B	0.7903	−0.1418	0.4618	0.053*
C12	0.9213 (2)	−0.0917 (2)	0.2549 (2)	0.0402 (6)
H12	0.9636	−0.0104	0.2967	0.048*
C13	0.7869 (2)	−0.2677 (2)	0.2088 (2)	0.0465 (6)
H13	0.7210	−0.3304	0.2117	0.056*
C14	0.8654 (3)	−0.2743 (2)	0.1202 (2)	0.0510 (7)
H14	0.8624	−0.3432	0.0500	0.061*
C15	1.0338 (2)	0.4758 (2)	0.2815 (2)	0.0376 (5)
C16	0.87617 (19)	0.45208 (19)	0.27283 (19)	0.0296 (5)
C17	0.8186 (2)	0.4650 (2)	0.3765 (2)	0.0392 (6)
H17	0.8761	0.4916	0.4503	0.047*
C18	0.6738 (2)	0.4386 (2)	0.3729 (2)	0.0385 (5)
H18	0.6374	0.4426	0.4438	0.046*
C19	0.58560 (19)	0.40728 (19)	0.26764 (19)	0.0294 (5)
C20	0.4319 (2)	0.3805 (2)	0.2734 (2)	0.0353 (5)
C21	0.64007 (19)	0.39844 (18)	0.15716 (18)	0.0255 (4)
C22	0.78814 (19)	0.41758 (18)	0.16013 (18)	0.0246 (4)
C23	0.8428 (2)	0.40779 (19)	0.05138 (19)	0.0314 (5)
H23	0.9393	0.4196	0.0527	0.038*
C24	0.7584 (2)	0.3816 (2)	−0.0548 (2)	0.0386 (5)
H24	0.7967	0.3765	−0.1251	0.046*
C25	0.6131 (2)	0.3624 (2)	−0.0577 (2)	0.0417 (6)
H25	0.5551	0.3439	−0.1306	0.050*
C26	0.5555 (2)	0.3705 (2)	0.04427 (19)	0.0357 (5)
H26	0.4587	0.3575	0.0400	0.043*
O1	0.39354 (17)	0.3166 (2)	0.3301 (2)	0.0755 (7)
O2	0.35024 (15)	0.43133 (18)	0.21712 (17)	0.0592 (5)
H2A	0.2689	0.4124	0.2246	0.089*
O1W	1.0555 (2)	0.7995 (2)	0.5309 (2)	0.0790 (6)
HW11	1.053 (4)	0.725 (2)	0.477 (3)	0.119*
HW12	0.991 (3)	0.788 (3)	0.569 (3)	0.119*
O3	1.09219 (15)	0.38750 (17)	0.21193 (16)	0.0525 (4)
O2W	0.1287 (2)	0.1769 (2)	0.2855 (3)	0.0908 (7)
HW21	0.204 (3)	0.224 (3)	0.313 (4)	0.136*
HW22	0.086 (4)	0.210 (4)	0.237 (3)	0.136*
O4	1.09571 (17)	0.57350 (19)	0.35306 (17)	0.0630 (5)
Ag1	0.91046 (2)	0.11314 (2)	−0.04497 (2)	0.05935 (10)
N1	0.64894 (18)	0.04051 (16)	0.19530 (16)	0.0346 (4)
N2	0.7687 (2)	0.05428 (19)	0.05184 (18)	0.0461 (5)
N3	0.82247 (17)	−0.15126 (17)	0.29391 (16)	0.0350 (4)
N4	0.95103 (19)	−0.16342 (18)	0.14922 (18)	0.0443 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0624 (17)	0.0469 (16)	0.0398 (14)	0.0010 (14)	0.0177 (12)	0.0115 (12)
C2	0.0520 (15)	0.0433 (15)	0.0415 (14)	−0.0066 (12)	0.0128 (11)	0.0145 (12)
C3	0.0452 (14)	0.0336 (13)	0.0498 (16)	−0.0008 (11)	0.0144 (12)	0.0151 (12)
C4	0.0566 (15)	0.0378 (14)	0.0404 (14)	0.0063 (12)	0.0215 (12)	0.0118 (11)
C5	0.0379 (13)	0.0377 (13)	0.0275 (12)	0.0048 (10)	0.0158 (10)	0.0089 (10)
C6	0.0396 (13)	0.0542 (16)	0.0362 (13)	0.0137 (12)	0.0109 (11)	0.0118 (12)
C7	0.0315 (13)	0.0632 (18)	0.0379 (14)	−0.0060 (12)	0.0124 (11)	0.0029 (13)
C8	0.0487 (15)	0.0441 (15)	0.0401 (14)	−0.0110 (13)	0.0201 (12)	0.0073 (12)
C9	0.0525 (15)	0.0419 (14)	0.0365 (13)	0.0076 (12)	0.0177 (11)	0.0162 (11)
C10	0.0337 (12)	0.0372 (13)	0.0272 (11)	0.0032 (10)	0.0134 (9)	0.0080 (10)
C11	0.0362 (13)	0.0569 (16)	0.0398 (14)	0.0055 (12)	0.0122 (11)	0.0143 (12)
C12	0.0309 (12)	0.0368 (13)	0.0545 (16)	0.0030 (10)	0.0133 (11)	0.0156 (12)
C13	0.0425 (14)	0.0290 (13)	0.0708 (18)	0.0033 (11)	0.0266 (13)	0.0157 (13)
C14	0.0514 (15)	0.0351 (14)	0.0646 (17)	0.0075 (12)	0.0272 (13)	0.0084 (13)
C15	0.0227 (11)	0.0521 (15)	0.0397 (14)	−0.0015 (11)	0.0024 (10)	0.0198 (12)
C16	0.0181 (10)	0.0340 (12)	0.0381 (13)	0.0033 (9)	0.0047 (9)	0.0138 (10)
C17	0.0228 (11)	0.0583 (16)	0.0344 (13)	0.0021 (11)	−0.0020 (9)	0.0155 (12)
C18	0.0269 (11)	0.0567 (15)	0.0342 (13)	0.0049 (11)	0.0103 (10)	0.0166 (11)
C19	0.0186 (10)	0.0339 (12)	0.0369 (13)	0.0056 (9)	0.0070 (9)	0.0122 (10)
C20	0.0224 (11)	0.0426 (14)	0.0408 (13)	0.0032 (10)	0.0089 (10)	0.0131 (11)
C21	0.0194 (10)	0.0240 (11)	0.0330 (12)	0.0043 (8)	0.0046 (9)	0.0090 (9)
C22	0.0191 (10)	0.0214 (10)	0.0321 (12)	0.0019 (8)	0.0042 (8)	0.0076 (9)
C23	0.0212 (10)	0.0320 (12)	0.0413 (13)	0.0025 (9)	0.0105 (10)	0.0114 (10)
C24	0.0377 (13)	0.0426 (14)	0.0344 (13)	0.0022 (11)	0.0095 (10)	0.0109 (11)
C25	0.0385 (13)	0.0503 (15)	0.0303 (13)	0.0017 (11)	−0.0035 (10)	0.0092 (11)
C26	0.0216 (11)	0.0423 (14)	0.0393 (13)	0.0015 (10)	0.0028 (10)	0.0095 (11)
O1	0.0282 (9)	0.1157 (17)	0.1216 (18)	0.0090 (10)	0.0207 (10)	0.0889 (15)
O2	0.0200 (8)	0.0928 (14)	0.0906 (14)	0.0163 (9)	0.0166 (9)	0.0605 (12)
O1W	0.0747 (15)	0.0615 (14)	0.0900 (17)	−0.0045 (12)	0.0228 (12)	0.0110 (12)
O3	0.0211 (8)	0.0636 (12)	0.0697 (12)	0.0109 (8)	0.0091 (8)	0.0167 (10)
O2W	0.0619 (14)	0.0779 (17)	0.146 (2)	−0.0041 (12)	0.0282 (14)	0.0553 (16)
O4	0.0303 (9)	0.0721 (13)	0.0657 (12)	−0.0156 (9)	0.0044 (9)	0.0014 (11)
Ag1	0.05254 (14)	0.07269 (17)	0.07007 (17)	0.00896 (11)	0.03247 (11)	0.03988 (13)
N1	0.0398 (11)	0.0306 (10)	0.0364 (11)	0.0028 (9)	0.0122 (8)	0.0139 (9)
N2	0.0498 (12)	0.0460 (13)	0.0540 (14)	0.0089 (10)	0.0240 (10)	0.0268 (11)
N3	0.0284 (10)	0.0357 (11)	0.0442 (11)	0.0057 (8)	0.0121 (8)	0.0155 (9)
N4	0.0412 (11)	0.0414 (12)	0.0590 (14)	0.0097 (10)	0.0258 (10)	0.0221 (10)

C1—C2	1.351 (3)	C14—H14	0.9300
C1—N2	1.371 (3)	C15—O4	1.217 (3)
C1—H1	0.9300	C15—O3	1.279 (3)
C2—N1	1.355 (3)	C15—C16	1.513 (3)
C2—H2	0.9300	C16—C17	1.365 (3)
C3—N2	1.315 (3)	C16—C22	1.424 (3)
C3—N1	1.336 (3)	C17—C18	1.402 (3)
C3—H3	0.9300	C17—H17	0.9300
C4—N1	1.477 (3)	C18—C19	1.360 (3)
C4—C5	1.508 (3)	C18—H18	0.9300
C4—H4A	0.9700	C19—C21	1.433 (3)
C4—H4B	0.9700	C19—C20	1.506 (3)
C5—C6	1.381 (3)	C20—O1	1.203 (3)
C5—C10	1.393 (3)	C20—O2	1.273 (3)
C6—C7	1.387 (3)	C21—C26	1.417 (3)
C6—H6	0.9300	C21—C22	1.426 (3)
C7—C8	1.359 (4)	C22—C23	1.413 (3)
C7—H7	0.9300	C23—C24	1.356 (3)
C8—C9	1.379 (3)	C23—H23	0.9300
C8—H8	0.9300	C24—C25	1.400 (3)
C9—C10	1.389 (3)	C24—H24	0.9300
C9—H9	0.9300	C25—C26	1.357 (3)
C10—C11	1.515 (3)	C25—H25	0.9300
C11—N3	1.468 (3)	C26—H26	0.9300
C11—H11A	0.9700	O2—H2A	0.8200
C11—H11B	0.9700	O1W—HW11	0.874 (17)
C12—N4	1.320 (3)	O1W—HW12	0.833 (17)
C12—N3	1.334 (3)	O2W—HW21	0.838 (18)
C12—H12	0.9300	O2W—HW22	0.882 (18)
C13—C14	1.340 (3)	Ag1—N2	2.0783 (17)
C13—N3	1.364 (3)	Ag1—N4i	2.0787 (17)
C13—H13	0.9300	N4—Ag1i	2.0787 (17)
C14—N4	1.373 (3)
C2—C1—N2	109.2 (2)	O3—C15—C16	115.7 (2)
C2—C1—H1	125.4	C17—C16—C22	119.93 (18)
N2—C1—H1	125.4	C17—C16—C15	118.49 (18)
C1—C2—N1	106.6 (2)	C22—C16—C15	121.58 (17)
C1—C2—H2	126.7	C16—C17—C18	120.8 (2)
N1—C2—H2	126.7	C16—C17—H17	119.6
N2—C3—N1	111.2 (2)	C18—C17—H17	119.6
N2—C3—H3	124.4	C19—C18—C17	121.12 (19)
N1—C3—H3	124.4	C19—C18—H18	119.4
N1—C4—C5	112.57 (18)	C17—C18—H18	119.4
N1—C4—H4A	109.1	C18—C19—C21	120.19 (17)
C5—C4—H4A	109.1	C18—C19—C20	117.02 (18)
N1—C4—H4B	109.1	C21—C19—C20	122.78 (18)
C5—C4—H4B	109.1	O1—C20—O2	124.30 (19)
H4A—C4—H4B	107.8	O1—C20—C19	120.2 (2)
C6—C5—C10	118.62 (19)	O2—C20—C19	115.45 (18)
C6—C5—C4	118.8 (2)	C26—C21—C22	117.74 (17)
C10—C5—C4	122.5 (2)	C26—C21—C19	123.92 (17)
C5—C6—C7	121.6 (2)	C22—C21—C19	118.34 (17)
C5—C6—H6	119.2	C23—C22—C16	121.85 (17)
C7—C6—H6	119.2	C23—C22—C21	118.69 (18)
C8—C7—C6	119.7 (2)	C16—C22—C21	119.38 (17)
C8—C7—H7	120.2	C24—C23—C22	121.85 (19)
C6—C7—H7	120.2	C24—C23—H23	119.1
C7—C8—C9	119.7 (2)	C22—C23—H23	119.1
C7—C8—H8	120.2	C23—C24—C25	119.4 (2)
C9—C8—H8	120.2	C23—C24—H24	120.3
C8—C9—C10	121.4 (2)	C25—C24—H24	120.3
C8—C9—H9	119.3	C26—C25—C24	121.0 (2)
C10—C9—H9	119.3	C26—C25—H25	119.5
C9—C10—C5	119.0 (2)	C24—C25—H25	119.5
C9—C10—C11	118.4 (2)	C25—C26—C21	121.34 (19)
C5—C10—C11	122.57 (19)	C25—C26—H26	119.3
N3—C11—C10	111.23 (18)	C21—C26—H26	119.3
N3—C11—H11A	109.4	C20—O2—H2A	109.5
C10—C11—H11A	109.4	HW11—O1W—HW12	101 (2)
N3—C11—H11B	109.4	HW21—O2W—HW22	103 (2)
C10—C11—H11B	109.4	N2—Ag1—N4i	177.04 (8)
H11A—C11—H11B	108.0	C3—N1—C2	107.41 (18)
N4—C12—N3	111.1 (2)	C3—N1—C4	124.93 (19)
N4—C12—H12	124.5	C2—N1—C4	127.65 (18)
N3—C12—H12	124.5	C3—N2—C1	105.65 (18)
C14—C13—N3	106.6 (2)	C3—N2—Ag1	128.88 (16)
C14—C13—H13	126.7	C1—N2—Ag1	125.46 (16)
N3—C13—H13	126.7	C12—N3—C13	107.32 (19)
C13—C14—N4	109.5 (2)	C12—N3—C11	126.2 (2)
C13—C14—H14	125.3	C13—N3—C11	126.49 (18)
N4—C14—H14	125.3	C12—N4—C14	105.53 (18)
O4—C15—O3	124.9 (2)	C12—N4—Ag1i	126.65 (15)
O4—C15—C16	119.4 (2)	C14—N4—Ag1i	127.71 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3ii	0.82	1.69	2.496 (2)	166
O1W—HW11···O4	0.87 (2)	1.96 (2)	2.814 (3)	166 (3)
O1W—HW12···O2Wiii	0.83 (2)	2.12 (2)	2.902 (3)	158 (3)
O2W—HW21···O1	0.84 (2)	1.99 (2)	2.810 (3)	164 (4)
O2W—HW22···O3ii	0.88 (2)	2.13 (3)	2.841 (3)	138 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O3i	0.82	1.69	2.496 (2)	166
O1W—HW11⋯O4	0.87 (2)	1.96 (2)	2.814 (3)	166 (3)
O1W—HW12⋯O2Wii	0.83 (2)	2.12 (2)	2.902 (3)	158 (3)
O2W—HW21⋯O1	0.84 (2)	1.99 (2)	2.810 (3)	164 (4)
O2W—HW22⋯O3i	0.88 (2)	2.13 (3)	2.841 (3)	138 (3)

Symmetry codes: (i) ; (ii) .