(1H-Benzimidazole-5-carb-oxy-lic acid-κN)(1H-benzimidazole-6-carb-oxy-lic acid-κN)silver(I) perchlorate.

The reaction of 1H-benzimidazole-5-carb-oxy-lic acid with silver nitrate in the presence of perchloric acid under hydro-thermal conditions yielded the title complex, [Ag(C(8)H(6)N(2)O(2))(2)]ClO(4), which comprises of an [Ag(C(8)H(6)N(2)O(2))(2)] mononuclear cation and a perchlorate anion. The Ag(I) ion is coordinated by two N atoms from two different neutral 1H-benzimidazole-5-carb-oxy-lic acid ligands with an N-Ag-N bond angle of 163.21 (14)°, forming an [Ag(C(8)H(6)N(2)O(2))(2)] mononuclear cation. Although both ligands in the mononuclear cation are monodentate with one N atom coordinated to the metal ion, they are different: one is N(3) coordinated to the Ag (I) ion and the N(1) atom protonated, the other with the N(1) coordinated to the Ag (I) ion and the N(3) atom protonated (and thus formally a 1H-benzimidazole-6-carb-oxy-lic acid rather than a 1H-benzimidazole-5-carb-oxy-lic acid ligand). The planes of the two planar ligands are roughly perpendicular, making a dihedral angle of 84.97 (2)°. The packing of the ions is stablized by extensive O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds, and by remote Ag⋯O inter-actions [3.002 (3), 3.581 (5) and 3.674 (5) Å].

Related literature

For related structures, see: Guo, Cao et al. (2007 ▶); Guo, Li et al. (2007 ▶); Liu et al. (2005 ▶); Peng, Ma et al. (2010 ▶); Peng, Qiu et al. (2010 ▶). For graph-set motifs of hydrogen bonds, see: Bernstein et al. (1995 ▶); Eppel & Bernstein (2008 ▶); Grell et al. (1999 ▶). For n class="Disease">van der Waals radii, see: Bondi (1964 ▶).

Experimental

Crystal data

[Ag(C8H6N2O2)2]n class="Chemical">ClO4

M = 531.62

Triclinic,

a = 4.933 (2) Å

b = 13.330 (5) Å

c = 14.498 (6) Å

α = 78.566 (5)°

β = 89.111 (5)°

γ = 82.554 (5)°

V = 926.5 (6) Å3

Z = 2

Mo Kα radiation

μ = 1.29 mm−1

T = 296 K

0.26 × 0.24 × 0.22 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.746, T max = 0.774

4604 measured reflections

3247 independent reflections

2630 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.103

S = 1.04

3247 reflections

273 parameters

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −0.70 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAIn class="Chemical">NT; 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/S1600536811010427/zl2355sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010427/zl2355Isup2.hkl

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

[Ag(C8H6N2O2)2]ClO4	Z = 2
Mr = 531.62	F(000) = 528.0
Triclinic, P1	Dx = 1.906 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.933 (2) Å	Cell parameters from 3317 reflections
b = 13.330 (5) Å	θ = 1.6–25.2°
c = 14.498 (6) Å	µ = 1.29 mm−1
α = 78.566 (5)°	T = 296 K
β = 89.111 (5)°	Prism, yellow
γ = 82.554 (5)°	0.26 × 0.24 × 0.22 mm
V = 926.5 (6) Å3

Bruker SMART APEX CCD diffractometer	3247 independent reflections
Radiation source: fine-focus sealed tube	2630 reflections with I > 2σ(I)
graphite	Rint = 0.017
ω scans	θmax = 25.2°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→5
Tmin = 0.746, Tmax = 0.774	k = −15→13
4604 measured reflections	l = −16→17

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0581P)2 + 0.3563P] where P = (Fo2 + 2Fc2)/3
3247 reflections	(Δ/σ)max = 0.001
273 parameters	Δρmax = 0.62 e Å−3
0 restraints	Δρmin = −0.70 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
Ag1	0.44123 (8)	0.70811 (3)	0.15898 (2)	0.04721 (15)
C1	0.6189 (10)	0.4842 (4)	0.1256 (3)	0.0466 (11)
H1	0.7430	0.5057	0.0793	0.056*
C2	0.3124 (8)	0.4843 (3)	0.2325 (3)	0.0346 (9)
C3	0.3830 (9)	0.3825 (3)	0.2238 (3)	0.0408 (10)
C4	0.2654 (10)	0.3021 (4)	0.2792 (3)	0.0509 (12)
H4	0.3152	0.2338	0.2738	0.061*
C5	0.0729 (10)	0.3286 (3)	0.3421 (3)	0.0471 (11)
H5	−0.0092	0.2766	0.3804	0.057*
C6	−0.0052 (9)	0.4309 (3)	0.3509 (3)	0.0396 (10)
C7	0.1163 (9)	0.5103 (3)	0.2959 (3)	0.0391 (10)
H7	0.0675	0.5786	0.3016	0.047*
C8	−0.2186 (10)	0.4595 (3)	0.4175 (3)	0.0446 (11)
C9	0.4393 (10)	0.9464 (4)	0.1285 (3)	0.0456 (11)
H9	0.3170	0.9604	0.0780	0.055*
C10	0.6828 (9)	0.8675 (3)	0.2492 (3)	0.0371 (10)
C11	0.7374 (9)	0.9692 (3)	0.2309 (3)	0.0381 (10)
C12	0.9185 (9)	1.0038 (3)	0.2866 (3)	0.0421 (10)
H12	0.9543	1.0719	0.2747	0.050*
C13	1.0426 (9)	0.9313 (3)	0.3608 (3)	0.0390 (10)
C14	0.9860 (10)	0.8291 (4)	0.3798 (3)	0.0482 (11)
H14	1.0709	0.7827	0.4308	0.058*
C15	0.8066 (10)	0.7964 (3)	0.3241 (3)	0.0460 (11)
H15	0.7694	0.7284	0.3364	0.055*
C16	1.2386 (10)	0.9636 (4)	0.4219 (3)	0.0457 (11)
Cl1	0.9204 (2)	0.77011 (9)	0.97296 (8)	0.0448 (3)
N1	0.4642 (7)	0.5474 (3)	0.1693 (2)	0.0408 (9)
N2	0.5791 (8)	0.3854 (3)	0.1548 (3)	0.0493 (10)
H2	0.6610	0.3333	0.1343	0.059*
N3	0.4956 (8)	0.8550 (3)	0.1829 (2)	0.0415 (9)
N4	0.5779 (8)	1.0176 (3)	0.1536 (3)	0.0470 (9)
H4A	0.5686	1.0815	0.1264	0.056*
O1	−0.3280 (8)	0.3835 (2)	0.4671 (3)	0.0581 (9)
H1A	−0.4557	0.4062	0.4972	0.087*
O2	−0.2846 (7)	0.5503 (2)	0.4241 (2)	0.0608 (10)
O3	1.3333 (8)	0.8956 (3)	0.4925 (3)	0.0672 (10)
H3	1.4522	0.9178	0.5187	0.101*
O4	1.3026 (8)	1.0534 (3)	0.4028 (2)	0.0630 (10)
O5	1.0476 (7)	0.7959 (3)	0.8839 (2)	0.0603 (9)
O6	0.6290 (6)	0.7811 (3)	0.9620 (2)	0.0577 (9)
O7	1.0171 (10)	0.6657 (4)	1.0117 (4)	0.1079 (18)
O8	0.9910 (9)	0.8361 (5)	1.0309 (4)	0.117 (2)

	U11	U22	U33	U12	U13	U23
Ag1	0.0531 (3)	0.0393 (2)	0.0526 (2)	−0.01424 (16)	0.00379 (16)	−0.01219 (16)
C1	0.042 (3)	0.052 (3)	0.049 (3)	−0.009 (2)	0.008 (2)	−0.013 (2)
C2	0.031 (2)	0.035 (2)	0.038 (2)	−0.0045 (17)	−0.0032 (17)	−0.0080 (18)
C3	0.043 (3)	0.039 (2)	0.043 (2)	−0.005 (2)	0.0001 (19)	−0.014 (2)
C4	0.060 (3)	0.033 (2)	0.060 (3)	−0.004 (2)	0.006 (2)	−0.013 (2)
C5	0.056 (3)	0.035 (2)	0.050 (3)	−0.013 (2)	0.006 (2)	−0.005 (2)
C6	0.039 (3)	0.038 (2)	0.040 (2)	−0.0033 (19)	−0.0002 (19)	−0.0044 (19)
C7	0.041 (3)	0.031 (2)	0.046 (2)	−0.0022 (19)	0.0006 (19)	−0.0109 (19)
C8	0.047 (3)	0.038 (3)	0.047 (3)	−0.008 (2)	0.005 (2)	−0.002 (2)
C9	0.048 (3)	0.048 (3)	0.042 (2)	−0.006 (2)	−0.003 (2)	−0.013 (2)
C10	0.038 (3)	0.037 (2)	0.037 (2)	−0.0034 (19)	0.0048 (18)	−0.0102 (18)
C11	0.041 (3)	0.035 (2)	0.038 (2)	−0.0028 (19)	−0.0024 (19)	−0.0081 (18)
C12	0.047 (3)	0.034 (2)	0.045 (3)	−0.005 (2)	−0.003 (2)	−0.007 (2)
C13	0.035 (2)	0.041 (2)	0.040 (2)	−0.0063 (19)	0.0032 (18)	−0.0078 (19)
C14	0.057 (3)	0.043 (3)	0.040 (3)	−0.001 (2)	−0.004 (2)	−0.001 (2)
C15	0.057 (3)	0.032 (2)	0.049 (3)	−0.008 (2)	−0.001 (2)	−0.006 (2)
C16	0.048 (3)	0.051 (3)	0.038 (2)	−0.002 (2)	0.000 (2)	−0.010 (2)
Cl1	0.0334 (6)	0.0542 (7)	0.0455 (6)	−0.0021 (5)	−0.0026 (5)	−0.0084 (5)
N1	0.041 (2)	0.038 (2)	0.044 (2)	−0.0047 (17)	0.0058 (16)	−0.0087 (17)
N2	0.055 (3)	0.040 (2)	0.056 (2)	−0.0027 (18)	0.0131 (19)	−0.0196 (18)
N3	0.046 (2)	0.037 (2)	0.043 (2)	−0.0096 (17)	0.0016 (16)	−0.0109 (17)
N4	0.058 (3)	0.033 (2)	0.047 (2)	−0.0052 (18)	−0.0090 (18)	−0.0014 (17)
O1	0.059 (2)	0.0433 (19)	0.068 (2)	−0.0067 (16)	0.0241 (17)	−0.0017 (16)
O2	0.071 (3)	0.0371 (19)	0.071 (2)	−0.0037 (17)	0.0301 (19)	−0.0084 (16)
O3	0.079 (3)	0.066 (2)	0.054 (2)	−0.016 (2)	−0.0255 (19)	−0.0008 (19)
O4	0.072 (3)	0.054 (2)	0.064 (2)	−0.0176 (19)	−0.0196 (18)	−0.0074 (18)
O5	0.060 (2)	0.067 (2)	0.052 (2)	−0.0115 (19)	0.0080 (16)	−0.0069 (17)
O6	0.0317 (18)	0.064 (2)	0.075 (2)	−0.0046 (16)	−0.0046 (15)	−0.0080 (18)
O7	0.077 (3)	0.087 (3)	0.125 (4)	0.011 (3)	0.004 (3)	0.051 (3)
O8	0.060 (3)	0.199 (6)	0.128 (4)	−0.023 (3)	0.010 (3)	−0.120 (4)

Ag1—N1	2.106 (4)	C10—C15	1.383 (6)
Ag1—N3	2.106 (4)	C10—C11	1.390 (6)
C1—N1	1.313 (6)	C10—N3	1.391 (5)
C1—N2	1.340 (6)	C11—N4	1.379 (5)
C1—H1	0.9300	C11—C12	1.393 (6)
C2—C7	1.383 (6)	C12—C13	1.386 (6)
C2—C3	1.387 (6)	C12—H12	0.9300
C2—N1	1.394 (5)	C13—C14	1.399 (6)
C3—N2	1.379 (6)	C13—C16	1.480 (6)
C3—C4	1.392 (6)	C14—C15	1.373 (6)
C4—C5	1.368 (7)	C14—H14	0.9300
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.399 (6)	C16—O4	1.255 (6)
C5—H5	0.9300	C16—O3	1.275 (5)
C6—C7	1.390 (6)	Cl1—O8	1.408 (4)
C6—C8	1.482 (6)	Cl1—O7	1.416 (4)
C7—H7	0.9300	Cl1—O5	1.426 (4)
C8—O2	1.234 (5)	Cl1—O6	1.434 (3)
C8—O1	1.294 (5)	N2—H2	0.8600
C9—N3	1.312 (6)	N4—H4A	0.8600
C9—N4	1.348 (6)	O1—H1A	0.8200
C9—H9	0.9300	O3—H3	0.8200
N1—Ag1—N3	163.21 (14)	C13—C12—H12	121.7
N1—C1—N2	112.9 (4)	C11—C12—H12	121.7
N1—C1—H1	123.6	C12—C13—C14	121.9 (4)
N2—C1—H1	123.6	C12—C13—C16	118.8 (4)
C7—C2—C3	121.0 (4)	C14—C13—C16	119.3 (4)
C7—C2—N1	129.7 (4)	C15—C14—C13	120.8 (4)
C3—C2—N1	109.3 (4)	C15—C14—H14	119.6
N2—C3—C2	105.3 (4)	C13—C14—H14	119.6
N2—C3—C4	132.8 (4)	C14—C15—C10	118.1 (4)
C2—C3—C4	122.0 (4)	C14—C15—H15	121.0
C5—C4—C3	116.6 (4)	C10—C15—H15	121.0
C5—C4—H4	121.7	O4—C16—O3	123.8 (4)
C3—C4—H4	121.7	O4—C16—C13	120.1 (4)
C4—C5—C6	122.4 (4)	O3—C16—C13	116.1 (4)
C4—C5—H5	118.8	O8—Cl1—O7	111.1 (4)
C6—C5—H5	118.8	O8—Cl1—O5	108.7 (3)
C7—C6—C5	120.4 (4)	O7—Cl1—O5	107.5 (3)
C7—C6—C8	117.4 (4)	O8—Cl1—O6	109.9 (2)
C5—C6—C8	122.3 (4)	O7—Cl1—O6	109.1 (3)
C2—C7—C6	117.7 (4)	O5—Cl1—O6	110.6 (2)
C2—C7—H7	121.2	C1—N1—C2	105.0 (4)
C6—C7—H7	121.2	C1—N1—Ag1	131.1 (3)
O2—C8—O1	123.2 (4)	C2—N1—Ag1	123.9 (3)
O2—C8—C6	121.2 (4)	C1—N2—C3	107.5 (4)
O1—C8—C6	115.6 (4)	C1—N2—H2	126.2
N3—C9—N4	112.7 (4)	C3—N2—H2	126.2
N3—C9—H9	123.7	C9—N3—C10	105.3 (4)
N4—C9—H9	123.7	C9—N3—Ag1	130.1 (3)
C15—C10—C11	121.0 (4)	C10—N3—Ag1	121.7 (3)
C15—C10—N3	129.7 (4)	C9—N4—C11	107.4 (4)
C11—C10—N3	109.2 (4)	C9—N4—H4A	126.3
N4—C11—C10	105.4 (4)	C11—N4—H4A	126.3
N4—C11—C12	133.0 (4)	C8—O1—H1A	109.5
C10—C11—C12	121.7 (4)	C16—O3—H3	109.5
C13—C12—C11	116.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2i	0.82	1.82	2.634 (5)	173
N2—H2···O5ii	0.86	2.15	2.983 (6)	163
O3—H3···O4iii	0.82	1.80	2.608 (6)	168
N4—H4A···O6iv	0.86	2.14	2.935 (6)	153
C14—H14···O3	0.93	2.41	2.729 (6)	100
C14—H14···O1v	0.93	2.60	3.491 (6)	162
C15—H15···O2vi	0.93	2.51	3.398 (5)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2i	0.82	1.82	2.634 (5)	173
N2—H2⋯O5ii	0.86	2.15	2.983 (6)	163
O3—H3⋯O4iii	0.82	1.80	2.608 (6)	168
N4—H4A⋯O6iv	0.86	2.14	2.935 (6)	153
C14—H14⋯O1v	0.93	2.60	3.491 (6)	162
C15—H15⋯O2vi	0.93	2.51	3.398 (5)	161

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .