Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055213/bt2575sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055213/bt2575Isup2.hkl |
CCDC reference: 603384
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.008 Å
- R factor = 0.061
- wR factor = 0.188
- Data-to-parameter ratio = 15.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT213_ALERT_2_C Atom O2 has ADP max/min Ratio ............. 3.30 prola PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for S1
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
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 0 ALERT type 5 Informative message, check
For related structures, see: Yuan et al. (2001); Xiong et al. (2001); Su et al. (1999). For related literature, see: Alcade et al. (1992).
A solution of Ag2O (0.07 g, 0.30 mmol), 2-(3-pyridyl)benzimidazole (Alcade et al., 1992) (0.14 g, 0.61 mmol) 4-sulfobenzoic acid (0.06 g, 0.30 mmol) and H2O (15 ml) was stirred under ambient condition and then sealed in teflon-lined stainless steel vessel, heated at 403 K for 4 days and cooled to room temperature for 3 days, creating the colorless crystals of the title compound.
All H atoms were fixed geometrically and allowed to ride on their attached atoms with C—H=0.93 Å, N—H=0.86 Å and U(H) = 1.2 Ueq(C,N).
Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear (Rigaku, 2000); data reduction: CrystalClear (Rigaku, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure (Rigaku, 2000); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
[Ag2(C6H4S2O6)(C12H9N3)2] | Z = 2 |
Mr = 421.20 | F(000) = 418 |
Triclinic, P1 | Dx = 1.979 Mg m−3 |
Hall symbol: -p 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.547 (3) Å | Cell parameters from 2133 reflections |
b = 10.060 (4) Å | θ = 2.9–27.5° |
c = 10.286 (4) Å | µ = 1.59 mm−1 |
α = 77.262 (11)° | T = 293 K |
β = 69.963 (11)° | Prism, colorless |
γ = 77.409 (10)° | 0.60 × 0.35 × 0.10 mm |
V = 706.9 (5) Å3 |
Rigaku Mercury CCD diffractometer | 3152 independent reflections |
Radiation source: Rotating Anode | 2784 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
ω scan | θmax = 27.5°, θmin = 2.9° |
Absorption correction: multi-scan (CrystalStructure; Rigaku, 2000) | h = −9→9 |
Tmin = 0.518, Tmax = 0.850 | k = −13→13 |
5340 measured reflections | l = −8→13 |
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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.188 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.1114P)2 + 1.6836P] where P = (Fo2 + 2Fc2)/3 |
3152 reflections | (Δ/σ)max < 0.001 |
208 parameters | Δρmax = 0.85 e Å−3 |
0 restraints | Δρmin = −1.86 e Å−3 |
[Ag2(C6H4S2O6)(C12H9N3)2] | γ = 77.409 (10)° |
Mr = 421.20 | V = 706.9 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.547 (3) Å | Mo Kα radiation |
b = 10.060 (4) Å | µ = 1.59 mm−1 |
c = 10.286 (4) Å | T = 293 K |
α = 77.262 (11)° | 0.60 × 0.35 × 0.10 mm |
β = 69.963 (11)° |
Rigaku Mercury CCD diffractometer | 3152 independent reflections |
Absorption correction: multi-scan (CrystalStructure; Rigaku, 2000) | 2784 reflections with I > 2σ(I) |
Tmin = 0.518, Tmax = 0.850 | Rint = 0.020 |
5340 measured reflections |
R[F2 > 2σ(F2)] = 0.061 | 0 restraints |
wR(F2) = 0.188 | H-atom parameters constrained |
S = 1.11 | Δρmax = 0.85 e Å−3 |
3152 reflections | Δρmin = −1.86 e Å−3 |
208 parameters |
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 | 0.21136 (7) | 0.66405 (5) | 0.12969 (4) | 0.0504 (2) | |
S1 | −0.2367 (3) | 0.7926 (2) | 0.1437 (2) | 0.0657 (5) | |
C1 | 0.7242 (8) | 0.1820 (6) | 0.1720 (6) | 0.0411 (12) | |
H1A | 0.8100 | 0.1153 | 0.1224 | 0.049* | |
C2 | 0.6483 (9) | 0.1494 (6) | 0.3124 (7) | 0.0450 (13) | |
H2A | 0.6849 | 0.0623 | 0.3579 | 0.054* | |
C3 | 0.5173 (8) | 0.2445 (6) | 0.3881 (6) | 0.0406 (12) | |
H3A | 0.4635 | 0.2218 | 0.4845 | 0.049* | |
C4 | 0.4660 (7) | 0.3754 (5) | 0.3187 (5) | 0.0288 (9) | |
C5 | 0.5556 (8) | 0.4020 (6) | 0.1745 (6) | 0.0378 (11) | |
H5A | 0.5274 | 0.4899 | 0.1269 | 0.045* | |
C6 | 0.3252 (7) | 0.4808 (5) | 0.3941 (5) | 0.0283 (9) | |
C7 | 0.1248 (7) | 0.6644 (5) | 0.4484 (5) | 0.0304 (9) | |
C8 | 0.0034 (8) | 0.7919 (6) | 0.4505 (6) | 0.0393 (12) | |
H8A | −0.0086 | 0.8474 | 0.3678 | 0.047* | |
C9 | −0.0988 (9) | 0.8330 (6) | 0.5804 (7) | 0.0446 (13) | |
H9A | −0.1781 | 0.9178 | 0.5850 | 0.054* | |
C10 | −0.0815 (10) | 0.7451 (7) | 0.7058 (7) | 0.0476 (14) | |
H10A | −0.1530 | 0.7730 | 0.7915 | 0.057* | |
C11 | 0.0369 (8) | 0.6208 (6) | 0.7045 (6) | 0.0394 (11) | |
H11A | 0.0479 | 0.5646 | 0.7871 | 0.047* | |
C12 | 0.1399 (7) | 0.5822 (5) | 0.5741 (5) | 0.0306 (10) | |
C13 | −0.3807 (7) | 0.9099 (5) | 0.0677 (6) | 0.0321 (10) | |
C14 | −0.5786 (7) | 0.9207 (5) | 0.1275 (5) | 0.0346 (10) | |
H14A | −0.6305 | 0.8677 | 0.2134 | 0.042* | |
C15 | −0.3035 (7) | 0.9905 (5) | −0.0596 (6) | 0.0357 (11) | |
H15A | −0.1718 | 0.9843 | −0.0990 | 0.043* | |
N1 | 0.6796 (7) | 0.3085 (5) | 0.1011 (5) | 0.0400 (10) | |
N2 | 0.2393 (6) | 0.5984 (4) | 0.3372 (4) | 0.0307 (8) | |
N3 | 0.2692 (6) | 0.4672 (4) | 0.5352 (4) | 0.0327 (9) | |
H3B | 0.3074 | 0.3988 | 0.5909 | 0.039* | |
O1 | −0.0735 (7) | 0.8405 (6) | 0.1194 (6) | 0.0690 (16) | |
O2 | −0.3410 (9) | 0.7512 (7) | 0.2775 (6) | 0.087 (2) | |
O3 | −0.179 (3) | 0.6689 (9) | 0.0723 (15) | 0.173 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.0630 (4) | 0.0477 (3) | 0.0345 (3) | 0.0168 (2) | −0.0243 (2) | −0.0043 (2) |
S1 | 0.0677 (12) | 0.0610 (11) | 0.0589 (11) | 0.0008 (9) | −0.0245 (9) | 0.0067 (9) |
C1 | 0.043 (3) | 0.035 (3) | 0.046 (3) | 0.007 (2) | −0.023 (2) | −0.008 (2) |
C2 | 0.051 (3) | 0.025 (2) | 0.051 (3) | 0.002 (2) | −0.016 (3) | 0.003 (2) |
C3 | 0.040 (3) | 0.032 (2) | 0.039 (3) | −0.001 (2) | −0.009 (2) | 0.006 (2) |
C4 | 0.028 (2) | 0.025 (2) | 0.033 (2) | −0.0015 (17) | −0.0134 (18) | 0.0005 (18) |
C5 | 0.043 (3) | 0.033 (3) | 0.032 (3) | 0.010 (2) | −0.016 (2) | −0.003 (2) |
C6 | 0.031 (2) | 0.027 (2) | 0.026 (2) | −0.0049 (18) | −0.0126 (18) | 0.0012 (17) |
C7 | 0.030 (2) | 0.028 (2) | 0.033 (2) | −0.0055 (18) | −0.0107 (18) | −0.0022 (18) |
C8 | 0.042 (3) | 0.028 (2) | 0.044 (3) | 0.000 (2) | −0.014 (2) | −0.003 (2) |
C9 | 0.051 (3) | 0.037 (3) | 0.047 (3) | −0.005 (2) | −0.014 (3) | −0.012 (2) |
C10 | 0.056 (4) | 0.048 (3) | 0.040 (3) | −0.011 (3) | −0.007 (3) | −0.019 (3) |
C11 | 0.044 (3) | 0.044 (3) | 0.031 (3) | −0.011 (2) | −0.010 (2) | −0.006 (2) |
C12 | 0.034 (2) | 0.029 (2) | 0.031 (2) | −0.0069 (18) | −0.0118 (19) | −0.0027 (18) |
C13 | 0.033 (2) | 0.022 (2) | 0.037 (3) | 0.0004 (18) | −0.010 (2) | −0.0032 (18) |
C14 | 0.035 (2) | 0.031 (2) | 0.029 (2) | −0.0045 (19) | −0.0035 (19) | 0.0011 (19) |
C15 | 0.025 (2) | 0.036 (2) | 0.039 (3) | −0.0014 (19) | −0.0043 (19) | −0.004 (2) |
N1 | 0.042 (2) | 0.039 (2) | 0.034 (2) | 0.0123 (19) | −0.0174 (19) | −0.0069 (18) |
N2 | 0.033 (2) | 0.0275 (19) | 0.029 (2) | −0.0023 (16) | −0.0105 (16) | −0.0005 (15) |
N3 | 0.039 (2) | 0.028 (2) | 0.030 (2) | −0.0018 (17) | −0.0138 (17) | 0.0006 (16) |
O1 | 0.036 (2) | 0.087 (4) | 0.070 (3) | 0.006 (2) | −0.026 (2) | 0.016 (3) |
O2 | 0.069 (3) | 0.105 (5) | 0.058 (3) | −0.004 (3) | −0.030 (3) | 0.050 (3) |
O3 | 0.280 (16) | 0.066 (5) | 0.213 (12) | 0.038 (7) | −0.158 (12) | −0.039 (6) |
Ag1—N2 | 2.159 (4) | C7—N2 | 1.379 (7) |
Ag1—N1i | 2.205 (5) | C7—C8 | 1.404 (7) |
Ag1—O1 | 2.489 (5) | C7—C12 | 1.399 (7) |
S1—O1 | 1.344 (6) | C8—C9 | 1.396 (8) |
S1—O2 | 1.355 (6) | C8—H8A | 0.9300 |
S1—O3 | 1.491 (10) | C9—C10 | 1.422 (9) |
S1—C13 | 1.674 (5) | C9—H9A | 0.9300 |
C1—C2 | 1.352 (9) | C10—C11 | 1.369 (9) |
C1—N1 | 1.355 (7) | C10—H10A | 0.9300 |
C1—H1A | 0.9300 | C11—C12 | 1.391 (7) |
C2—C3 | 1.374 (8) | C11—H11A | 0.9300 |
C2—H2A | 0.9300 | C12—N3 | 1.377 (7) |
C3—C4 | 1.396 (7) | C13—C15 | 1.388 (7) |
C3—H3A | 0.9300 | C13—C14 | 1.396 (7) |
C4—C5 | 1.395 (7) | C14—C15ii | 1.371 (8) |
C4—C6 | 1.471 (7) | C14—H14A | 0.9300 |
C5—N1 | 1.333 (7) | C15—C14ii | 1.371 (8) |
C5—H5A | 0.9300 | C15—H15A | 0.9300 |
C6—N2 | 1.335 (6) | N3—O2iii | 2.677 (6) |
C6—N3 | 1.349 (6) | N3—H3B | 0.8600 |
N2—Ag1—N1i | 153.94 (18) | C8—C9—C10 | 120.0 (6) |
N2—Ag1—O1 | 114.05 (18) | C8—C9—H9A | 120.0 |
N1i—Ag1—O1 | 90.56 (18) | C10—C9—H9A | 120.0 |
O1—S1—O2 | 119.3 (4) | C11—C10—C9 | 122.2 (6) |
O1—S1—O3 | 105.1 (8) | C11—C10—H10A | 118.9 |
O2—S1—O3 | 106.4 (7) | C9—C10—H10A | 118.9 |
O1—S1—C13 | 109.6 (3) | C10—C11—C12 | 117.1 (5) |
O2—S1—C13 | 107.7 (3) | C10—C11—H11A | 121.5 |
O3—S1—C13 | 108.3 (5) | C12—C11—H11A | 121.5 |
C2—C1—N1 | 122.3 (5) | N3—C12—C11 | 132.2 (5) |
C2—C1—H1A | 118.9 | N3—C12—C7 | 105.2 (4) |
N1—C1—H1A | 118.9 | C11—C12—C7 | 122.6 (5) |
C1—C2—C3 | 120.2 (5) | C15—C13—C14 | 119.9 (5) |
C1—C2—H2A | 119.9 | C15—C13—S1 | 119.9 (4) |
C3—C2—H2A | 119.9 | C14—C13—S1 | 120.1 (4) |
C2—C3—C4 | 119.2 (5) | C15ii—C14—C13 | 120.0 (5) |
C2—C3—H3A | 120.4 | C15ii—C14—H14A | 120.0 |
C4—C3—H3A | 120.4 | C13—C14—H14A | 120.0 |
C3—C4—C5 | 116.9 (5) | C14ii—C15—C13 | 120.1 (5) |
C3—C4—C6 | 121.6 (5) | C14ii—C15—H15A | 120.0 |
C5—C4—C6 | 121.5 (4) | C13—C15—H15A | 120.0 |
N1—C5—C4 | 123.6 (5) | C5—N1—C1 | 117.8 (5) |
N1—C5—H5A | 118.2 | C5—N1—Ag1i | 124.4 (4) |
C4—C5—H5A | 118.2 | C1—N1—Ag1i | 117.3 (4) |
N2—C6—N3 | 111.8 (4) | C6—N2—C7 | 105.5 (4) |
N2—C6—C4 | 126.7 (4) | C6—N2—Ag1 | 131.1 (4) |
N3—C6—C4 | 121.6 (4) | C7—N2—Ag1 | 121.9 (3) |
N2—C7—C8 | 130.4 (5) | C6—N3—C12 | 108.0 (4) |
N2—C7—C12 | 109.6 (4) | C6—N3—O2iii | 129.2 (4) |
C8—C7—C12 | 120.0 (5) | C12—N3—O2iii | 122.3 (4) |
C7—C8—C9 | 118.0 (5) | C6—N3—H3B | 126.0 |
C7—C8—H8A | 121.0 | C12—N3—H3B | 126.0 |
C9—C8—H8A | 121.0 | S1—O1—Ag1 | 116.3 (4) |
N1—C1—C2—C3 | 1.8 (10) | S1—C13—C15—C14ii | 175.0 (4) |
C1—C2—C3—C4 | −0.9 (9) | C4—C5—N1—C1 | −1.9 (9) |
C2—C3—C4—C5 | −1.1 (8) | C4—C5—N1—Ag1i | 169.8 (4) |
C2—C3—C4—C6 | 179.4 (5) | C2—C1—N1—C5 | −0.4 (9) |
C3—C4—C5—N1 | 2.6 (8) | C2—C1—N1—Ag1i | −172.7 (5) |
C6—C4—C5—N1 | −177.9 (5) | N3—C6—N2—C7 | 1.2 (5) |
C3—C4—C6—N2 | −166.6 (5) | C4—C6—N2—C7 | −178.3 (4) |
C5—C4—C6—N2 | 14.0 (8) | N3—C6—N2—Ag1 | −164.2 (3) |
C3—C4—C6—N3 | 14.0 (7) | C4—C6—N2—Ag1 | 16.3 (7) |
C5—C4—C6—N3 | −165.5 (5) | C8—C7—N2—C6 | 179.5 (5) |
N2—C7—C8—C9 | 179.2 (5) | C12—C7—N2—C6 | −1.5 (5) |
C12—C7—C8—C9 | 0.4 (8) | C8—C7—N2—Ag1 | −13.4 (7) |
C7—C8—C9—C10 | −1.4 (9) | C12—C7—N2—Ag1 | 165.5 (3) |
C8—C9—C10—C11 | 1.6 (9) | N1i—Ag1—N2—C6 | −46.3 (6) |
C9—C10—C11—C12 | −0.6 (9) | O1—Ag1—N2—C6 | 154.2 (4) |
C10—C11—C12—N3 | 179.8 (5) | N1i—Ag1—N2—C7 | 150.3 (4) |
C10—C11—C12—C7 | −0.5 (8) | O1—Ag1—N2—C7 | −9.2 (4) |
N2—C7—C12—N3 | 1.3 (5) | N2—C6—N3—C12 | −0.4 (5) |
C8—C7—C12—N3 | −179.6 (4) | C4—C6—N3—C12 | 179.1 (4) |
N2—C7—C12—C11 | −178.5 (5) | N2—C6—N3—O2iii | 171.1 (4) |
C8—C7—C12—C11 | 0.6 (7) | C4—C6—N3—O2iii | −9.3 (7) |
O1—S1—C13—C15 | 35.5 (6) | C11—C12—N3—C6 | 179.2 (5) |
O2—S1—C13—C15 | 166.7 (6) | C7—C12—N3—C6 | −0.6 (5) |
O3—S1—C13—C15 | −78.7 (9) | C11—C12—N3—O2iii | 6.9 (8) |
O1—S1—C13—C14 | −148.6 (5) | C7—C12—N3—O2iii | −172.8 (3) |
O2—S1—C13—C14 | −17.4 (7) | O2—S1—O1—Ag1 | 79.7 (5) |
O3—S1—C13—C14 | 97.2 (9) | O3—S1—O1—Ag1 | −39.4 (6) |
C15—C13—C14—C15ii | 0.8 (9) | C13—S1—O1—Ag1 | −155.6 (3) |
S1—C13—C14—C15ii | −175.0 (4) | N2—Ag1—O1—S1 | −86.9 (4) |
C14—C13—C15—C14ii | −0.8 (9) | N1i—Ag1—O1—S1 | 101.9 (4) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x−1, −y+2, −z; (iii) −x, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3B···O2iii | 0.86 | 1.83 | 2.677 (6) | 169 |
Symmetry code: (iii) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Ag2(C6H4S2O6)(C12H9N3)2] |
Mr | 421.20 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 7.547 (3), 10.060 (4), 10.286 (4) |
α, β, γ (°) | 77.262 (11), 69.963 (11), 77.409 (10) |
V (Å3) | 706.9 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.59 |
Crystal size (mm) | 0.60 × 0.35 × 0.10 |
Data collection | |
Diffractometer | Rigaku Mercury CCD diffractometer |
Absorption correction | Multi-scan (CrystalStructure; Rigaku, 2000) |
Tmin, Tmax | 0.518, 0.850 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5340, 3152, 2784 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.188, 1.11 |
No. of reflections | 3152 |
No. of parameters | 208 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.85, −1.86 |
Computer programs: CrystalClear (Rigaku, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), CrystalStructure (Rigaku, 2000).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3B···O2i | 0.86 | 1.83 | 2.677 (6) | 169.1 |
Symmetry code: (i) −x, −y+1, −z+1. |
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4-sulfobenzoic acid is an efficient O donor ligand, exhibiting versatile coordination mode and hydrogen bonding interaction in the assembly of metal-organic coordination polymers (Yuan et al., 2001), 4-sulfobenzoic acid could be in situ synthesized into benzene-1,4-disulfonate (Xiong et al., 2001). 2-(3-pyridyl)benzimidazole has been reported to connect the AgI ions, resulting in a binuclear macrocyclic (Su et al., 1999). Herein, we report the synthesis and structure of the coordination polymer on the basis of bridging benzene-1,4-disulfonate ligands and [Ag2(C12H9N3)2] binuclear units.
In the title compound, AgI exhibits a distorted trigonal planar geometry (Fig. 1). Each two AgI atoms are connected with two 2-(3-pyridyl)benzimidazole ligands in the end to end mode via Npy and NBIm donor atoms, forming a binuclear macrocyclic. The coordination sphere of AgI is completed by an oxygen atom from benzene-1,4-disulfonate with bis(monodentate) coordination fashion. The bridging benzene-1,4-disulfonate ligands link the binuclear units, forming a chain (Fig. 2). The chains are assembled into a two-dimensional network by the N—H···O hydrogen bonds as well as π-π interactions between the benzimidazolyl rings of 2-(3-pyridyl)benzimidazole ligands (the perpendicular distance is about 3.43 Å) (Fig. 3). The crystal packing can be viewed as layered arrangement of the two-dimensional supramolecular networks (Fig. 4).