In the binuclear title complex, [Ag
2(C
9H
5O
6)
2(C
12H
9N
3)
2], the two Ag
I atoms are in a trigonal planar environment formed by two N atoms from two 2-(3-pyridyl)benzimidazole ligands and one O atom from a 3,5-dicarboxybenzoate ligand, forming a centrosymmetric cyclic dimer. Intermolecular N—H
O and O—H
O hydrogen-bonding interactions aggregate the binuclear units into a three-dimensional framework.
Supporting information
CCDC reference: 603383
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.030
- wR factor = 0.070
- Data-to-parameter ratio = 14.2
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Ag1 - O2 .. 19.25 su
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Ag1 (9) 0.86
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
0 ALERT level C = Check and explain
4 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
The 2-(3-pyridyl)benzimidazole was synthesized according to the literature
(Alcalde et al., 1992). A solution of AgNO3 (0.104 g, 0.61 mmol),
2-(3-pyridyl)benzimidazole (0.14 g, 0.61 mmol), 1,3,5-benzenetricarboxylatic
acid (0.128 g, 0.61 mmol) and H2O (15 ml) was stirred under ambient
condition, adjust with dilute NaOH to pH=7.3, then sealed in Teflon-lined
stainless steel vessel, heated at 403 K for 4 days and cooled to room
temperature. The resulting product was recovered by filtration, washed with
distilled water and dried in air. (60% yield).
After checking their presence in the different map, H atoms bonded to C and N
were fixed geometrically and allowed to ride on their attached atoms, with
C—H=0.93 Å, N—H=0.86 Å, Uiso(H)=1.2Ueq(C,N). The
two carboxylic acid H atoms were located from a difference map and refined
with a restraint of 0.83 (1)Å for the O—H distance.
Data collection: CrystalClear (Rigaku, 2002); cell refinement: CrystalClear (Rigaku, 2002); data reduction: CrystalClear (Rigaku, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Siemens, 1994); software used to prepare material for publication: SHELXL97.
Bis[µ-2-(3-pyridyl)benzimidazole]bis[bis(3,5-dicarboxybenzoato)silver(I)]
top
Crystal data top
[Ag2(C9H5O6)2(C12H9N3)2] | F(000) = 1024 |
Mr = 1024.44 | Dx = 1.880 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -p 2ybc | Cell parameters from 4455 reflections |
a = 14.573 (3) Å | θ = 2.2–27.5° |
b = 7.7160 (15) Å | µ = 1.16 mm−1 |
c = 16.662 (4) Å | T = 293 K |
β = 105.038 (3)° | Prism, white |
V = 1809.3 (7) Å3 | 0.30 × 0.20 × 0.10 mm |
Z = 2 | |
Data collection top
Rigaku Mercury CCD diffractometer | 4111 independent reflections |
Radiation source: fine-focus sealed tube | 3895 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
ω scan | θmax = 27.5°, θmin = 2.5° |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2002) | h = −18→17 |
Tmin = 0.756, Tmax = 0.881 | k = −9→9 |
13327 measured reflections | l = −21→21 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.030 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.070 | w = 1/[σ2(Fo2) + (0.0272P)2 + 1.8597P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
4111 reflections | Δρmax = 0.57 e Å−3 |
289 parameters | Δρmin = −0.80 e Å−3 |
2 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0084 (4) |
Crystal data top
[Ag2(C9H5O6)2(C12H9N3)2] | V = 1809.3 (7) Å3 |
Mr = 1024.44 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.573 (3) Å | µ = 1.16 mm−1 |
b = 7.7160 (15) Å | T = 293 K |
c = 16.662 (4) Å | 0.30 × 0.20 × 0.10 mm |
β = 105.038 (3)° | |
Data collection top
Rigaku Mercury CCD diffractometer | 4111 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2002) | 3895 reflections with I > 2σ(I) |
Tmin = 0.756, Tmax = 0.881 | Rint = 0.021 |
13327 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.030 | 2 restraints |
wR(F2) = 0.070 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | Δρmax = 0.57 e Å−3 |
4111 reflections | Δρmin = −0.80 e Å−3 |
289 parameters | |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
Ag1 | 0.382999 (13) | 0.29268 (3) | 0.037544 (12) | 0.03468 (9) | |
C1 | 0.74977 (16) | 0.5248 (3) | 0.11466 (15) | 0.0309 (5) | |
H1A | 0.7874 | 0.6219 | 0.1140 | 0.037* | |
C2 | 0.77957 (18) | 0.4034 (3) | 0.17668 (16) | 0.0368 (6) | |
H2A | 0.8373 | 0.4177 | 0.2161 | 0.044* | |
C3 | 0.72380 (17) | 0.2614 (3) | 0.18019 (14) | 0.0295 (5) | |
H3A | 0.7427 | 0.1799 | 0.2224 | 0.035* | |
C4 | 0.63816 (14) | 0.2416 (3) | 0.11918 (13) | 0.0217 (4) | |
C5 | 0.61437 (14) | 0.3674 (3) | 0.05766 (13) | 0.0243 (4) | |
H5A | 0.5583 | 0.3538 | 0.0161 | 0.029* | |
C6 | 0.57592 (14) | 0.0933 (3) | 0.12172 (12) | 0.0220 (4) | |
C7 | 0.45294 (15) | −0.0690 (3) | 0.11505 (13) | 0.0236 (4) | |
C8 | 0.36146 (16) | −0.1367 (3) | 0.10454 (15) | 0.0309 (5) | |
H8A | 0.3076 | −0.0719 | 0.0802 | 0.037* | |
C9 | 0.35464 (18) | −0.3034 (3) | 0.13187 (16) | 0.0332 (5) | |
H9A | 0.2948 | −0.3523 | 0.1254 | 0.040* | |
C10 | 0.43580 (18) | −0.4018 (3) | 0.16943 (14) | 0.0318 (5) | |
H10A | 0.4282 | −0.5142 | 0.1869 | 0.038* | |
C11 | 0.52649 (17) | −0.3358 (3) | 0.18106 (14) | 0.0290 (5) | |
H11A | 0.5801 | −0.4003 | 0.2064 | 0.035* | |
C12 | 0.53314 (15) | −0.1673 (3) | 0.15278 (13) | 0.0233 (4) | |
C13 | 0.20664 (14) | 0.2894 (3) | 0.16465 (13) | 0.0202 (4) | |
C14 | 0.10780 (14) | 0.2457 (3) | 0.11280 (12) | 0.0202 (4) | |
C15 | 0.08006 (15) | 0.2934 (3) | 0.02933 (13) | 0.0214 (4) | |
H15A | 0.1229 | 0.3486 | 0.0051 | 0.026* | |
C16 | −0.01229 (15) | 0.2581 (3) | −0.01784 (12) | 0.0226 (4) | |
C17 | −0.04769 (16) | 0.3129 (3) | −0.10631 (13) | 0.0263 (5) | |
C18 | −0.07455 (15) | 0.1672 (3) | 0.01709 (13) | 0.0239 (4) | |
H18A | −0.1354 | 0.1415 | −0.0150 | 0.029* | |
C19 | −0.04660 (14) | 0.1142 (3) | 0.09960 (13) | 0.0216 (4) | |
C20 | −0.11372 (14) | 0.0066 (3) | 0.13342 (13) | 0.0238 (4) | |
C21 | 0.04383 (14) | 0.1585 (3) | 0.14761 (12) | 0.0207 (4) | |
H21A | 0.0616 | 0.1293 | 0.2037 | 0.025* | |
N1 | 0.66800 (12) | 0.5074 (2) | 0.05512 (11) | 0.0248 (4) | |
N2 | 0.48148 (12) | 0.0938 (2) | 0.09546 (11) | 0.0238 (4) | |
N3 | 0.60976 (12) | −0.0606 (2) | 0.15547 (11) | 0.0249 (4) | |
H3B | 0.6686 | −0.0873 | 0.1751 | 0.030* | |
O1 | 0.21436 (10) | 0.3257 (2) | 0.24162 (9) | 0.0267 (3) | |
O2 | 0.27345 (12) | 0.2860 (3) | 0.13320 (11) | 0.0373 (4) | |
O3 | 0.01671 (12) | 0.3937 (3) | −0.13642 (10) | 0.0334 (4) | |
H3C | −0.012 (2) | 0.424 (5) | −0.1850 (13) | 0.059 (10)* | |
O4 | −0.12813 (13) | 0.2879 (3) | −0.14653 (11) | 0.0483 (5) | |
O5 | −0.19001 (11) | −0.0415 (3) | 0.08971 (10) | 0.0354 (4) | |
O6 | −0.08317 (11) | −0.0325 (2) | 0.21275 (9) | 0.0290 (4) | |
H6B | −0.127 (2) | −0.084 (5) | 0.228 (2) | 0.072 (12)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ag1 | 0.02870 (11) | 0.03189 (13) | 0.04170 (13) | 0.00498 (7) | 0.00598 (8) | 0.01359 (8) |
C1 | 0.0279 (11) | 0.0267 (12) | 0.0363 (12) | −0.0075 (9) | 0.0050 (9) | 0.0005 (10) |
C2 | 0.0318 (12) | 0.0334 (14) | 0.0365 (13) | −0.0084 (10) | −0.0069 (10) | 0.0042 (11) |
C3 | 0.0276 (11) | 0.0291 (12) | 0.0276 (11) | −0.0021 (9) | −0.0005 (9) | 0.0054 (9) |
C4 | 0.0199 (9) | 0.0218 (10) | 0.0231 (10) | −0.0003 (8) | 0.0048 (8) | −0.0011 (8) |
C5 | 0.0198 (9) | 0.0272 (11) | 0.0247 (10) | 0.0001 (8) | 0.0037 (8) | 0.0025 (9) |
C6 | 0.0211 (9) | 0.0228 (11) | 0.0215 (9) | 0.0001 (8) | 0.0042 (7) | 0.0002 (8) |
C7 | 0.0227 (10) | 0.0238 (11) | 0.0245 (10) | −0.0006 (8) | 0.0064 (8) | 0.0007 (8) |
C8 | 0.0210 (10) | 0.0330 (13) | 0.0383 (12) | −0.0016 (9) | 0.0072 (9) | 0.0000 (10) |
C9 | 0.0286 (11) | 0.0353 (14) | 0.0384 (13) | −0.0099 (10) | 0.0133 (10) | −0.0032 (10) |
C10 | 0.0436 (13) | 0.0250 (12) | 0.0294 (11) | −0.0070 (10) | 0.0142 (10) | 0.0012 (9) |
C11 | 0.0334 (12) | 0.0240 (11) | 0.0277 (11) | 0.0015 (9) | 0.0049 (9) | 0.0034 (9) |
C12 | 0.0218 (10) | 0.0232 (11) | 0.0237 (10) | −0.0004 (8) | 0.0035 (8) | −0.0009 (8) |
C13 | 0.0178 (9) | 0.0196 (10) | 0.0231 (9) | −0.0016 (8) | 0.0050 (7) | 0.0000 (8) |
C14 | 0.0175 (9) | 0.0228 (10) | 0.0201 (9) | −0.0001 (8) | 0.0045 (7) | −0.0037 (8) |
C15 | 0.0227 (10) | 0.0216 (11) | 0.0211 (9) | −0.0001 (8) | 0.0078 (8) | −0.0008 (8) |
C16 | 0.0243 (10) | 0.0241 (11) | 0.0184 (9) | 0.0008 (8) | 0.0036 (8) | −0.0015 (8) |
C17 | 0.0283 (11) | 0.0287 (12) | 0.0206 (10) | 0.0036 (9) | 0.0039 (8) | −0.0007 (9) |
C18 | 0.0197 (9) | 0.0264 (11) | 0.0232 (10) | −0.0002 (8) | 0.0014 (8) | −0.0038 (8) |
C19 | 0.0197 (9) | 0.0210 (10) | 0.0236 (10) | −0.0026 (8) | 0.0051 (7) | −0.0025 (8) |
C20 | 0.0205 (9) | 0.0246 (11) | 0.0265 (10) | 0.0003 (8) | 0.0064 (8) | −0.0029 (9) |
C21 | 0.0208 (9) | 0.0221 (10) | 0.0184 (9) | 0.0005 (8) | 0.0037 (7) | −0.0001 (8) |
N1 | 0.0224 (9) | 0.0256 (10) | 0.0268 (9) | 0.0004 (7) | 0.0069 (7) | 0.0036 (7) |
N2 | 0.0198 (8) | 0.0240 (10) | 0.0264 (9) | 0.0009 (7) | 0.0040 (7) | 0.0024 (7) |
N3 | 0.0183 (8) | 0.0231 (9) | 0.0310 (9) | 0.0012 (7) | 0.0023 (7) | 0.0034 (8) |
O1 | 0.0187 (7) | 0.0379 (9) | 0.0216 (7) | −0.0007 (6) | 0.0017 (6) | −0.0071 (6) |
O2 | 0.0223 (8) | 0.0587 (13) | 0.0342 (9) | −0.0062 (8) | 0.0135 (7) | −0.0057 (8) |
O3 | 0.0291 (8) | 0.0483 (11) | 0.0225 (8) | 0.0030 (8) | 0.0061 (6) | 0.0082 (7) |
O4 | 0.0313 (9) | 0.0744 (15) | 0.0297 (9) | −0.0118 (9) | −0.0093 (7) | 0.0133 (9) |
O5 | 0.0254 (8) | 0.0451 (11) | 0.0321 (8) | −0.0132 (7) | 0.0010 (6) | 0.0028 (8) |
O6 | 0.0237 (8) | 0.0391 (10) | 0.0239 (7) | −0.0098 (7) | 0.0057 (6) | 0.0003 (7) |
Geometric parameters (Å, º) top
Ag1—N2 | 2.1508 (18) | C11—H11A | 0.9300 |
Ag1—N1i | 2.1729 (18) | C12—N3 | 1.378 (3) |
Ag1—O2 | 2.5320 (17) | C13—O2 | 1.220 (3) |
C1—N1 | 1.345 (3) | C13—O1 | 1.289 (3) |
C1—C2 | 1.379 (3) | C13—C14 | 1.513 (3) |
C1—H1A | 0.9300 | C14—C15 | 1.393 (3) |
C2—C3 | 1.375 (3) | C14—C21 | 1.392 (3) |
C2—H2A | 0.9300 | C15—C16 | 1.398 (3) |
C3—C4 | 1.399 (3) | C15—H15A | 0.9300 |
C3—H3A | 0.9300 | C16—C18 | 1.389 (3) |
C4—C5 | 1.389 (3) | C16—C17 | 1.491 (3) |
C4—C6 | 1.467 (3) | C17—O4 | 1.205 (3) |
C5—N1 | 1.340 (3) | C17—O3 | 1.329 (3) |
C5—H5A | 0.9300 | C18—C19 | 1.390 (3) |
C6—N2 | 1.331 (3) | C18—H18A | 0.9300 |
C6—N3 | 1.352 (3) | C19—C21 | 1.395 (3) |
C7—N2 | 1.389 (3) | C19—C20 | 1.500 (3) |
C7—C12 | 1.398 (3) | C20—O5 | 1.218 (3) |
C7—C8 | 1.400 (3) | C20—O6 | 1.316 (3) |
C8—C9 | 1.377 (4) | C21—H21A | 0.9300 |
C8—H8A | 0.9300 | N3—O1ii | 2.828 (2) |
C9—C10 | 1.408 (4) | N3—H3B | 0.8600 |
C9—H9A | 0.9300 | O3—O6iii | 2.772 (2) |
C10—C11 | 1.382 (3) | O3—H3C | 0.841 (18) |
C10—H10A | 0.9300 | O6—O1iv | 2.487 (2) |
C11—C12 | 1.395 (3) | O6—H6B | 0.841 (18) |
| | | |
N2—Ag1—N1i | 152.96 (7) | O1—C13—C14 | 116.17 (17) |
N2—Ag1—O2 | 99.17 (7) | C15—C14—C21 | 119.42 (18) |
N1i—Ag1—O2 | 107.84 (7) | C15—C14—C13 | 119.86 (18) |
N1—C1—C2 | 122.1 (2) | C21—C14—C13 | 120.72 (18) |
N1—C1—H1A | 119.0 | C14—C15—C16 | 119.83 (19) |
C2—C1—H1A | 119.0 | C14—C15—H15A | 120.1 |
C1—C2—C3 | 119.9 (2) | C16—C15—H15A | 120.1 |
C1—C2—H2A | 120.0 | C18—C16—C15 | 120.08 (19) |
C3—C2—H2A | 120.0 | C18—C16—C17 | 117.48 (19) |
C2—C3—C4 | 118.8 (2) | C15—C16—C17 | 122.4 (2) |
C2—C3—H3A | 120.6 | O4—C17—O3 | 123.1 (2) |
C4—C3—H3A | 120.6 | O4—C17—C16 | 122.8 (2) |
C5—C4—C3 | 117.7 (2) | O3—C17—C16 | 114.16 (19) |
C5—C4—C6 | 121.90 (19) | C19—C18—C16 | 120.49 (19) |
C3—C4—C6 | 120.4 (2) | C19—C18—H18A | 119.8 |
N1—C5—C4 | 123.40 (19) | C16—C18—H18A | 119.8 |
N1—C5—H5A | 118.3 | C18—C19—C21 | 119.07 (19) |
C4—C5—H5A | 118.3 | C18—C19—C20 | 118.82 (18) |
N2—C6—N3 | 111.94 (19) | C21—C19—C20 | 122.08 (19) |
N2—C6—C4 | 125.60 (19) | O5—C20—O6 | 123.3 (2) |
N3—C6—C4 | 122.40 (18) | O5—C20—C19 | 121.8 (2) |
N2—C7—C12 | 109.27 (18) | O6—C20—C19 | 114.88 (18) |
N2—C7—C8 | 129.9 (2) | C14—C21—C19 | 120.96 (19) |
C12—C7—C8 | 120.8 (2) | C14—C21—H21A | 119.5 |
C9—C8—C7 | 117.1 (2) | C19—C21—H21A | 119.5 |
C9—C8—H8A | 121.5 | C5—N1—C1 | 118.03 (19) |
C7—C8—H8A | 121.5 | C5—N1—Ag1i | 119.99 (14) |
C8—C9—C10 | 121.8 (2) | C1—N1—Ag1i | 121.82 (15) |
C8—C9—H9A | 119.1 | C6—N2—C7 | 105.49 (18) |
C10—C9—H9A | 119.1 | C6—N2—Ag1 | 131.45 (15) |
C11—C10—C9 | 121.7 (2) | C7—N2—Ag1 | 123.03 (14) |
C11—C10—H10A | 119.1 | C6—N3—C12 | 107.83 (17) |
C9—C10—H10A | 119.1 | C6—N3—O1ii | 134.45 (14) |
C10—C11—C12 | 116.3 (2) | C12—N3—O1ii | 115.70 (14) |
C10—C11—H11A | 121.8 | C6—N3—H3B | 126.1 |
C12—C11—H11A | 121.8 | C12—N3—H3B | 126.1 |
N3—C12—C11 | 132.2 (2) | C13—O2—Ag1 | 166.85 (16) |
N3—C12—C7 | 105.44 (19) | C17—O3—O6iii | 105.52 (13) |
C11—C12—C7 | 122.3 (2) | C17—O3—H3C | 106 (2) |
O2—C13—O1 | 123.97 (19) | C20—O6—O1iv | 108.75 (13) |
O2—C13—C14 | 119.85 (19) | C20—O6—H6B | 109 (3) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, y−1/2, −z+1/2; (iii) x, −y+1/2, z−1/2; (iv) −x, y−1/2, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3B···O1ii | 0.86 | 2.01 | 2.828 (2) | 158 |
O3—H3C···O6iii | 0.84 (2) | 1.94 (2) | 2.772 (2) | 169 (4) |
O6—H6B···O1iv | 0.84 (2) | 1.65 (2) | 2.487 (2) | 176 (4) |
Symmetry codes: (ii) −x+1, y−1/2, −z+1/2; (iii) x, −y+1/2, z−1/2; (iv) −x, y−1/2, −z+1/2. |
Experimental details
Crystal data |
Chemical formula | [Ag2(C9H5O6)2(C12H9N3)2] |
Mr | 1024.44 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 14.573 (3), 7.7160 (15), 16.662 (4) |
β (°) | 105.038 (3) |
V (Å3) | 1809.3 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.16 |
Crystal size (mm) | 0.30 × 0.20 × 0.10 |
|
Data collection |
Diffractometer | Rigaku Mercury CCD diffractometer |
Absorption correction | Multi-scan (CrystalClear; Rigaku, 2002) |
Tmin, Tmax | 0.756, 0.881 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13327, 4111, 3895 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.649 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.030, 0.070, 1.09 |
No. of reflections | 4111 |
No. of parameters | 289 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.57, −0.80 |
Selected geometric parameters (Å, º) topAg1—N2 | 2.1508 (18) | C17—O3 | 1.329 (3) |
Ag1—N1i | 2.1729 (18) | C20—O5 | 1.218 (3) |
Ag1—O2 | 2.5320 (17) | C20—O6 | 1.316 (3) |
C17—O4 | 1.205 (3) | | |
| | | |
N2—Ag1—N1i | 152.96 (7) | N1i—Ag1—O2 | 107.84 (7) |
N2—Ag1—O2 | 99.17 (7) | | |
Symmetry code: (i) −x+1, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3B···O1ii | 0.86 | 2.01 | 2.828 (2) | 157.6 |
O3—H3C···O6iii | 0.841 (18) | 1.941 (19) | 2.772 (2) | 169 (4) |
O6—H6B···O1iv | 0.841 (18) | 1.647 (19) | 2.487 (2) | 176 (4) |
Symmetry codes: (ii) −x+1, y−1/2, −z+1/2; (iii) x, −y+1/2, z−1/2; (iv) −x, y−1/2, −z+1/2. |
1,3,5-Benzenetricarboxylatic acid has been often be used to construct supramolecular structures (Dai et al., 2003, Prior et al., 2003; Plater et al., 2001). In those coordination complexes, the 1,3,5-benzenetricarboxylatic acid ligand demonstrated versatile coordination modes and the tendence of forming hydrogen bonds. The structures are controlled by the extent of the depronation of 1,3,5-benzenetricarboxylatic acid, the nature of the auxiliary ligands, and the metal centers.
In the title compound each two AgI atom is bonded by two nitrogen atoms from two two 2-(3-pyridyl)benzimidazole ligands, forming a binuclear macrocycle. The coordination sphere is completed by a 3,5-dicarboxybenzoate ligand. The intermolecular N—H···O hydrogen bonding interactions connect the binuclear units into a two-dimensional undulating sheet with the protonated carboxylic acid groups on the opposite sides (Fig. 2). The sheets are further connected by O—H···O hydrogen bonding interactions into a three-dimensional framework (Fig. 3). Although there are aromatic rings, no apparent π···π stacking interactions have been found.