Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049264/bt2531sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049264/bt2531Isup2.hkl |
CCDC reference: 667158
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.049
- wR factor = 0.100
- Data-to-parameter ratio = 15.3
checkCIF/PLATON results
No syntax errors found
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 Co1 (3) 1.83
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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
2-(2-pyridyl)benzimidazole was synthesized according to the literature method of Alcade et al. (1992). A solution of Co(CH3COO)2.4H2O (0.128 g, 0.51 mmol), 2-(2-pyridyl)benzimidazole (0.10 g, 0.51 mmol), benzene-1,4-dicarboxylatic acid (0.085 g, 0.51 mmol) and H2O (15 ml) stirred under ambient conditions, then sealed in a Teflon-lined steel vessel, heated at 160 °C for 5 days, and cooled to room temperature. The resulting product was recovered by filtration, washed with distilled water and dried in air (80% yield).
After checking their presence in the difference map, all H atoms were positioned geometrically and allowed to ride on their attached atoms with C—H and N—H bond lengths of 0.93–0.97Å and 0.86 Å, respectively, and Uiso(H) = 1.2Ueq(C,N).
benzene-1,4-dicarboxylatic acid is often used to bridge metal atoms with 2,2'-bipyridine or 1,10-phenanthroline as auxiliary ligands (Sun et al., 2001; Zhang et al., 2003; Cano et al., 1997). Those compounds demonstrate various network topologies. In the title compound the CoII atom is six coordinated (Fig. 1), bonded to two nitrogen atoms of the chelating 2-(2-pyridyl)benzimidazole ligand, and bridged by the benzene-1,4-dicarboxylate into a zigzag chain (Fig. 2). The chains are further connected into a three-dimensional framework via intermolecular N—H···O hydrogen bonds as well as π-π interactions (perpendicular distance: 3.54 Å, centroid···centroid distances: 3.678Å and 3.697 Å) (Fig. 3).
For related literature, see: Sun et al. (2001); Zhang et al. (2003); Cano et al. (1997); Alcade et al. (1992).
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: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
[Co(C8H4O4)(C12H9N3)] | F(000) = 852 |
Mr = 418.26 | Dx = 1.645 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -p 2ybc | Cell parameters from 3393 reflections |
a = 7.2518 (7) Å | θ = 3.2–27.5° |
b = 20.6995 (19) Å | µ = 1.05 mm−1 |
c = 11.3088 (11) Å | T = 293 K |
β = 95.914 (5)° | Prism, red |
V = 1688.5 (3) Å3 | 0.20 × 0.15 × 0.08 mm |
Z = 4 |
Rigaku CCD diffractometer | 3866 independent reflections |
Radiation source: fine-focus sealed tube | 3170 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
Detector resolution: 14.6306 pixels mm-1 | θmax = 27.5°, θmin = 3.3° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2002) | k = −24→26 |
Tmin = 0.828, Tmax = 0.923 | l = −14→14 |
12922 measured reflections |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0355P)2 + 1.1421P] where P = (Fo2 + 2Fc2)/3 |
3866 reflections | (Δ/σ)max = 0.001 |
253 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
[Co(C8H4O4)(C12H9N3)] | V = 1688.5 (3) Å3 |
Mr = 418.26 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.2518 (7) Å | µ = 1.05 mm−1 |
b = 20.6995 (19) Å | T = 293 K |
c = 11.3088 (11) Å | 0.20 × 0.15 × 0.08 mm |
β = 95.914 (5)° |
Rigaku CCD diffractometer | 3866 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2002) | 3170 reflections with I > 2σ(I) |
Tmin = 0.828, Tmax = 0.923 | Rint = 0.042 |
12922 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.40 e Å−3 |
3866 reflections | Δρmin = −0.40 e Å−3 |
253 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 | ||
Co1 | 0.21952 (5) | 0.389651 (17) | 0.65376 (3) | 0.02542 (12) | |
C1 | 0.1887 (4) | 0.51415 (16) | 0.8068 (3) | 0.0420 (7) | |
H1A | 0.1646 | 0.4867 | 0.8685 | 0.050* | |
C2 | 0.2052 (5) | 0.57978 (18) | 0.8292 (3) | 0.0541 (9) | |
H2A | 0.1906 | 0.5961 | 0.9042 | 0.065* | |
C3 | 0.2433 (5) | 0.62015 (16) | 0.7392 (3) | 0.0547 (10) | |
H3A | 0.2567 | 0.6643 | 0.7525 | 0.066* | |
C4 | 0.2617 (4) | 0.59479 (14) | 0.6290 (3) | 0.0421 (8) | |
H4A | 0.2882 | 0.6215 | 0.5668 | 0.051* | |
C5 | 0.2403 (4) | 0.52938 (13) | 0.6114 (2) | 0.0291 (6) | |
C6 | 0.2538 (3) | 0.49664 (12) | 0.4984 (2) | 0.0259 (5) | |
C7 | 0.2778 (4) | 0.47506 (14) | 0.3107 (2) | 0.0320 (6) | |
C8 | 0.2962 (5) | 0.47506 (16) | 0.1891 (3) | 0.0429 (8) | |
H8A | 0.3118 | 0.5131 | 0.1475 | 0.051* | |
C9 | 0.2899 (5) | 0.41577 (18) | 0.1343 (3) | 0.0498 (8) | |
H9A | 0.3018 | 0.4137 | 0.0533 | 0.060* | |
C10 | 0.2664 (5) | 0.35865 (16) | 0.1960 (3) | 0.0440 (8) | |
H10A | 0.2617 | 0.3197 | 0.1549 | 0.053* | |
C11 | 0.2500 (4) | 0.35825 (15) | 0.3156 (3) | 0.0375 (7) | |
H11A | 0.2354 | 0.3199 | 0.3565 | 0.045* | |
C12 | 0.2559 (4) | 0.41753 (13) | 0.3730 (2) | 0.0276 (6) | |
C13 | 0.4583 (4) | 0.35217 (12) | 0.8096 (2) | 0.0251 (5) | |
C14 | 0.6013 (4) | 0.31788 (12) | 0.8909 (2) | 0.0248 (5) | |
C15 | 0.7883 (4) | 0.32392 (13) | 0.8738 (2) | 0.0280 (6) | |
H15A | 0.8250 | 0.3527 | 0.8175 | 0.034* | |
C16 | 0.9190 (4) | 0.28677 (13) | 0.9411 (2) | 0.0297 (6) | |
H16A | 1.0440 | 0.2915 | 0.9314 | 0.036* | |
C17 | 0.8643 (3) | 0.24263 (12) | 1.0228 (2) | 0.0238 (5) | |
C18 | 1.0033 (4) | 0.19638 (13) | 1.0811 (2) | 0.0259 (6) | |
C19 | 0.6783 (4) | 0.23799 (13) | 1.0420 (2) | 0.0272 (6) | |
H19A | 0.6417 | 0.2093 | 1.0984 | 0.033* | |
C20 | 0.5484 (4) | 0.27602 (13) | 0.9769 (2) | 0.0276 (6) | |
H20A | 0.4244 | 0.2736 | 0.9910 | 0.033* | |
O1 | 0.2913 (3) | 0.35225 (10) | 0.83061 (17) | 0.0363 (5) | |
O2 | 0.5059 (2) | 0.37898 (9) | 0.71660 (16) | 0.0305 (4) | |
O3 | 1.1733 (2) | 0.20703 (9) | 1.08103 (17) | 0.0317 (4) | |
O4 | 0.9473 (2) | 0.14397 (9) | 1.12442 (16) | 0.0289 (4) | |
N1 | 0.2062 (3) | 0.48882 (11) | 0.7003 (2) | 0.0309 (5) | |
N2 | 0.2420 (3) | 0.43282 (10) | 0.49134 (18) | 0.0263 (5) | |
N3 | 0.2760 (3) | 0.52381 (11) | 0.3928 (2) | 0.0324 (5) | |
H3B | 0.2871 | 0.5644 | 0.3792 | 0.039* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.0241 (2) | 0.02434 (19) | 0.02722 (19) | −0.00096 (15) | −0.00035 (14) | 0.00107 (15) |
C1 | 0.0434 (18) | 0.0478 (19) | 0.0339 (15) | 0.0057 (15) | −0.0011 (14) | −0.0110 (14) |
C2 | 0.057 (2) | 0.057 (2) | 0.0458 (19) | 0.0125 (18) | −0.0064 (16) | −0.0267 (18) |
C3 | 0.065 (2) | 0.0334 (18) | 0.061 (2) | 0.0101 (16) | −0.0160 (18) | −0.0165 (16) |
C4 | 0.0448 (19) | 0.0275 (16) | 0.0506 (18) | 0.0008 (13) | −0.0115 (15) | −0.0029 (13) |
C5 | 0.0232 (14) | 0.0252 (14) | 0.0369 (14) | 0.0032 (11) | −0.0058 (11) | −0.0025 (11) |
C6 | 0.0214 (13) | 0.0234 (13) | 0.0317 (13) | 0.0003 (10) | −0.0026 (11) | 0.0021 (11) |
C7 | 0.0300 (15) | 0.0320 (15) | 0.0336 (14) | 0.0001 (12) | 0.0017 (12) | 0.0031 (12) |
C8 | 0.0472 (19) | 0.0464 (19) | 0.0355 (16) | −0.0029 (15) | 0.0065 (14) | 0.0095 (14) |
C9 | 0.058 (2) | 0.061 (2) | 0.0325 (16) | 0.0019 (18) | 0.0107 (15) | −0.0008 (16) |
C10 | 0.049 (2) | 0.0437 (19) | 0.0397 (16) | 0.0035 (15) | 0.0077 (15) | −0.0099 (15) |
C11 | 0.0410 (18) | 0.0315 (16) | 0.0412 (16) | −0.0003 (13) | 0.0101 (14) | −0.0042 (13) |
C12 | 0.0241 (14) | 0.0292 (14) | 0.0299 (13) | 0.0010 (11) | 0.0047 (11) | 0.0004 (11) |
C13 | 0.0254 (13) | 0.0239 (13) | 0.0257 (12) | −0.0022 (11) | 0.0006 (10) | −0.0011 (10) |
C14 | 0.0242 (13) | 0.0255 (13) | 0.0244 (12) | 0.0020 (11) | 0.0012 (10) | −0.0006 (10) |
C15 | 0.0260 (14) | 0.0291 (14) | 0.0295 (13) | −0.0017 (11) | 0.0059 (11) | 0.0064 (11) |
C16 | 0.0214 (13) | 0.0343 (15) | 0.0339 (14) | 0.0008 (11) | 0.0048 (11) | 0.0035 (12) |
C17 | 0.0222 (13) | 0.0241 (13) | 0.0250 (12) | 0.0015 (10) | 0.0018 (10) | −0.0021 (10) |
C18 | 0.0275 (14) | 0.0264 (14) | 0.0240 (12) | 0.0029 (11) | 0.0042 (11) | −0.0037 (10) |
C19 | 0.0272 (14) | 0.0275 (14) | 0.0276 (13) | 0.0000 (11) | 0.0064 (11) | 0.0041 (11) |
C20 | 0.0230 (13) | 0.0316 (15) | 0.0290 (13) | 0.0004 (11) | 0.0066 (11) | 0.0001 (11) |
O1 | 0.0231 (10) | 0.0493 (13) | 0.0364 (11) | 0.0021 (9) | 0.0030 (8) | 0.0105 (9) |
O2 | 0.0252 (10) | 0.0363 (11) | 0.0297 (9) | 0.0023 (8) | 0.0016 (8) | 0.0089 (8) |
O3 | 0.0228 (10) | 0.0272 (10) | 0.0443 (11) | 0.0010 (8) | −0.0004 (8) | 0.0019 (8) |
O4 | 0.0259 (10) | 0.0276 (10) | 0.0334 (10) | 0.0014 (8) | 0.0040 (8) | 0.0054 (8) |
N1 | 0.0286 (12) | 0.0315 (13) | 0.0315 (11) | 0.0010 (10) | −0.0015 (10) | −0.0046 (10) |
N2 | 0.0261 (12) | 0.0239 (11) | 0.0284 (11) | −0.0001 (9) | 0.0006 (9) | 0.0004 (9) |
N3 | 0.0375 (14) | 0.0215 (12) | 0.0375 (12) | −0.0010 (10) | 0.0000 (11) | 0.0064 (10) |
Co1—N2 | 2.064 (2) | C9—H9A | 0.9300 |
Co1—O4i | 2.0872 (18) | C10—C11 | 1.371 (4) |
Co1—N1 | 2.124 (2) | C10—H10A | 0.9300 |
Co1—O2 | 2.1362 (18) | C11—C12 | 1.387 (4) |
Co1—O1 | 2.1577 (19) | C11—H11A | 0.9300 |
Co1—O3i | 2.1765 (18) | C12—N2 | 1.389 (3) |
C1—N1 | 1.332 (4) | C13—O1 | 1.257 (3) |
C1—C2 | 1.385 (5) | C13—O2 | 1.268 (3) |
C1—H1A | 0.9300 | C13—C14 | 1.493 (3) |
C2—C3 | 1.367 (5) | C14—C20 | 1.386 (4) |
C2—H2A | 0.9300 | C14—C15 | 1.395 (3) |
C3—C4 | 1.371 (5) | C15—C16 | 1.386 (4) |
C3—H3A | 0.9300 | C15—H15A | 0.9300 |
C4—C5 | 1.375 (4) | C16—C17 | 1.386 (4) |
C4—H4A | 0.9300 | C16—H16A | 0.9300 |
C5—N1 | 1.352 (4) | C17—C19 | 1.392 (4) |
C5—C6 | 1.459 (4) | C17—C18 | 1.493 (4) |
C6—N2 | 1.326 (3) | C18—O3 | 1.253 (3) |
C6—N3 | 1.344 (3) | C18—O4 | 1.274 (3) |
C7—N3 | 1.372 (4) | C19—C20 | 1.381 (4) |
C7—C8 | 1.395 (4) | C19—H19A | 0.9300 |
C7—C12 | 1.401 (4) | C20—H20A | 0.9300 |
C8—C9 | 1.373 (5) | N3—O2ii | 2.913 (3) |
C8—H8A | 0.9300 | N3—O4iii | 2.963 (3) |
C9—C10 | 1.392 (5) | N3—H3B | 0.8600 |
N2—Co1—O4i | 99.39 (8) | C11—C10—H10A | 119.1 |
N2—Co1—N1 | 79.16 (9) | C9—C10—H10A | 119.1 |
O4i—Co1—N1 | 107.17 (8) | C10—C11—C12 | 117.1 (3) |
N2—Co1—O2 | 100.22 (8) | C10—C11—H11A | 121.5 |
O4i—Co1—O2 | 152.82 (7) | C12—C11—H11A | 121.5 |
N1—Co1—O2 | 94.88 (8) | C11—C12—N2 | 130.6 (3) |
N2—Co1—O1 | 161.16 (8) | C11—C12—C7 | 121.1 (3) |
O4i—Co1—O1 | 99.31 (7) | N2—C12—C7 | 108.3 (2) |
N1—Co1—O1 | 97.47 (9) | O1—C13—O2 | 120.4 (2) |
O2—Co1—O1 | 61.38 (7) | O1—C13—C14 | 120.4 (2) |
N2—Co1—O3i | 94.88 (8) | O2—C13—C14 | 119.2 (2) |
O4i—Co1—O3i | 61.77 (7) | O1—C13—Co1 | 61.04 (13) |
N1—Co1—O3i | 166.70 (8) | O2—C13—Co1 | 60.05 (13) |
O2—Co1—O3i | 97.89 (7) | C14—C13—Co1 | 169.17 (18) |
O1—Co1—O3i | 91.91 (8) | C20—C14—C15 | 119.8 (2) |
N2—Co1—C18i | 97.03 (8) | C20—C14—C13 | 120.3 (2) |
O4i—Co1—C18i | 31.22 (8) | C15—C14—C13 | 119.7 (2) |
N1—Co1—C18i | 137.68 (9) | C16—C15—C14 | 119.6 (2) |
O2—Co1—C18i | 126.96 (8) | C16—C15—H15A | 120.2 |
O1—Co1—C18i | 97.74 (8) | C14—C15—H15A | 120.2 |
O3i—Co1—C18i | 30.60 (7) | C17—C16—C15 | 120.4 (2) |
N2—Co1—C13 | 131.17 (9) | C17—C16—H16A | 119.8 |
O4i—Co1—C13 | 126.29 (8) | C15—C16—H16A | 119.8 |
N1—Co1—C13 | 100.00 (8) | C16—C17—C19 | 119.9 (2) |
O2—Co1—C13 | 30.95 (7) | C16—C17—C18 | 119.4 (2) |
O1—Co1—C13 | 30.65 (7) | C19—C17—C18 | 120.5 (2) |
O3i—Co1—C13 | 92.88 (8) | O3—C18—O4 | 120.2 (2) |
C18i—Co1—C13 | 112.83 (8) | O3—C18—C17 | 120.4 (2) |
N1—C1—C2 | 122.5 (3) | O4—C18—C17 | 119.2 (2) |
N1—C1—H1A | 118.8 | O3—C18—Co1iv | 62.20 (14) |
C2—C1—H1A | 118.8 | O4—C18—Co1iv | 58.13 (13) |
C3—C2—C1 | 118.9 (3) | C17—C18—Co1iv | 172.09 (18) |
C3—C2—H2A | 120.5 | C20—C19—C17 | 119.8 (2) |
C1—C2—H2A | 120.5 | C20—C19—H19A | 120.1 |
C2—C3—C4 | 119.3 (3) | C17—C19—H19A | 120.1 |
C2—C3—H3A | 120.4 | C19—C20—C14 | 120.5 (2) |
C4—C3—H3A | 120.4 | C19—C20—H20A | 119.8 |
C3—C4—C5 | 119.2 (3) | C14—C20—H20A | 119.8 |
C3—C4—H4A | 120.4 | C13—O1—Co1 | 88.31 (15) |
C5—C4—H4A | 120.4 | C13—O2—Co1 | 89.00 (15) |
N1—C5—C4 | 122.1 (3) | C18—O3—Co1iv | 87.20 (15) |
N1—C5—C6 | 113.4 (2) | C18—O4—Co1iv | 90.65 (15) |
C4—C5—C6 | 124.6 (3) | C1—N1—C5 | 118.0 (3) |
N2—C6—N3 | 112.1 (2) | C1—N1—Co1 | 128.0 (2) |
N2—C6—C5 | 120.4 (2) | C5—N1—Co1 | 113.55 (17) |
N3—C6—C5 | 127.5 (2) | C6—N2—C12 | 105.9 (2) |
N3—C7—C8 | 132.5 (3) | C6—N2—Co1 | 112.86 (17) |
N3—C7—C12 | 106.0 (2) | C12—N2—Co1 | 141.17 (18) |
C8—C7—C12 | 121.5 (3) | C6—N3—C7 | 107.7 (2) |
C9—C8—C7 | 116.3 (3) | C6—N3—O2ii | 141.83 (18) |
C9—C8—H8A | 121.9 | C7—N3—O2ii | 100.21 (17) |
C7—C8—H8A | 121.9 | C6—N3—O4iii | 107.15 (17) |
C8—C9—C10 | 122.2 (3) | C7—N3—O4iii | 128.03 (18) |
C8—C9—H9A | 118.9 | O2ii—N3—O4iii | 73.09 (7) |
C10—C9—H9A | 118.9 | C6—N3—H3B | 126.2 |
C11—C10—C9 | 121.8 (3) | C7—N3—H3B | 126.2 |
N1—C1—C2—C3 | −0.9 (5) | O1—C13—O2—Co1 | −9.6 (2) |
C1—C2—C3—C4 | 0.9 (5) | C14—C13—O2—Co1 | 167.6 (2) |
C2—C3—C4—C5 | 0.3 (5) | N2—Co1—O2—C13 | −178.84 (15) |
C3—C4—C5—N1 | −1.6 (5) | O4i—Co1—O2—C13 | −43.3 (2) |
C3—C4—C5—C6 | 179.1 (3) | N1—Co1—O2—C13 | 101.32 (16) |
N1—C5—C6—N2 | −3.3 (4) | O1—Co1—O2—C13 | 5.47 (14) |
C4—C5—C6—N2 | 176.0 (3) | O3i—Co1—O2—C13 | −82.40 (15) |
N1—C5—C6—N3 | 175.9 (3) | C18i—Co1—O2—C13 | −71.90 (17) |
C4—C5—C6—N3 | −4.8 (4) | O4—C18—O3—Co1iv | 4.1 (2) |
N3—C7—C8—C9 | −179.5 (3) | C17—C18—O3—Co1iv | −171.4 (2) |
C12—C7—C8—C9 | 0.6 (5) | O3—C18—O4—Co1iv | −4.3 (2) |
C7—C8—C9—C10 | 0.0 (5) | C17—C18—O4—Co1iv | 171.3 (2) |
C8—C9—C10—C11 | −0.7 (5) | C2—C1—N1—C5 | −0.3 (4) |
C9—C10—C11—C12 | 0.6 (5) | C2—C1—N1—Co1 | 171.6 (2) |
C10—C11—C12—N2 | 179.5 (3) | C4—C5—N1—C1 | 1.6 (4) |
C10—C11—C12—C7 | 0.0 (4) | C6—C5—N1—C1 | −179.1 (2) |
N3—C7—C12—C11 | 179.4 (3) | C4—C5—N1—Co1 | −171.4 (2) |
C8—C7—C12—C11 | −0.7 (4) | C6—C5—N1—Co1 | 7.9 (3) |
N3—C7—C12—N2 | −0.2 (3) | N2—Co1—N1—C1 | −179.7 (3) |
C8—C7—C12—N2 | 179.8 (3) | O4i—Co1—N1—C1 | 83.7 (3) |
N2—Co1—C13—O1 | 172.07 (15) | O2—Co1—N1—C1 | −80.2 (3) |
O4i—Co1—C13—O1 | −32.30 (19) | O1—Co1—N1—C1 | −18.5 (3) |
N1—Co1—C13—O1 | 87.79 (16) | O3i—Co1—N1—C1 | 116.0 (4) |
O2—Co1—C13—O1 | 170.6 (2) | C18i—Co1—N1—C1 | 91.7 (3) |
O3i—Co1—C13—O1 | −88.89 (16) | C13—Co1—N1—C1 | −49.4 (3) |
C18i—Co1—C13—O1 | −64.94 (17) | N2—Co1—N1—C5 | −7.54 (18) |
N2—Co1—C13—O2 | 1.5 (2) | O4i—Co1—N1—C5 | −104.12 (18) |
O4i—Co1—C13—O2 | 157.15 (13) | O2—Co1—N1—C5 | 91.96 (18) |
N1—Co1—C13—O2 | −82.77 (16) | O1—Co1—N1—C5 | 153.68 (18) |
O1—Co1—C13—O2 | −170.6 (2) | O3i—Co1—N1—C5 | −71.8 (4) |
O3i—Co1—C13—O2 | 100.56 (15) | C18i—Co1—N1—C5 | −96.1 (2) |
C18i—Co1—C13—O2 | 124.51 (15) | C13—Co1—N1—C5 | 122.76 (18) |
N2—Co1—C13—C14 | −87.5 (10) | N3—C6—N2—C12 | −0.5 (3) |
O4i—Co1—C13—C14 | 68.2 (10) | C5—C6—N2—C12 | 178.8 (2) |
N1—Co1—C13—C14 | −171.8 (10) | N3—C6—N2—Co1 | 177.46 (17) |
O2—Co1—C13—C14 | −89.0 (10) | C5—C6—N2—Co1 | −3.2 (3) |
O1—Co1—C13—C14 | 100.5 (10) | C11—C12—N2—C6 | −179.1 (3) |
O3i—Co1—C13—C14 | 11.6 (10) | C7—C12—N2—C6 | 0.4 (3) |
C18i—Co1—C13—C14 | 35.5 (10) | C11—C12—N2—Co1 | 3.9 (5) |
O1—C13—C14—C20 | 12.1 (4) | C7—C12—N2—Co1 | −176.6 (2) |
O2—C13—C14—C20 | −165.1 (2) | O4i—Co1—N2—C6 | 111.45 (18) |
Co1—C13—C14—C20 | −82.2 (10) | N1—Co1—N2—C6 | 5.60 (18) |
O1—C13—C14—C15 | −173.2 (2) | O2—Co1—N2—C6 | −87.46 (18) |
O2—C13—C14—C15 | 9.7 (4) | O1—Co1—N2—C6 | −75.7 (3) |
Co1—C13—C14—C15 | 92.5 (10) | O3i—Co1—N2—C6 | 173.60 (18) |
C20—C14—C15—C16 | 1.6 (4) | C18i—Co1—N2—C6 | 142.90 (18) |
C13—C14—C15—C16 | −173.2 (2) | C13—Co1—N2—C6 | −88.3 (2) |
C14—C15—C16—C17 | 1.7 (4) | O4i—Co1—N2—C12 | −71.6 (3) |
C15—C16—C17—C19 | −3.5 (4) | N1—Co1—N2—C12 | −177.5 (3) |
C15—C16—C17—C18 | 171.0 (2) | O2—Co1—N2—C12 | 89.5 (3) |
C16—C17—C18—O3 | 18.1 (4) | O1—Co1—N2—C12 | 101.2 (4) |
C19—C17—C18—O3 | −167.5 (2) | O3i—Co1—N2—C12 | −9.5 (3) |
C16—C17—C18—O4 | −157.5 (2) | C18i—Co1—N2—C12 | −40.2 (3) |
C19—C17—C18—O4 | 16.9 (4) | C13—Co1—N2—C12 | 88.7 (3) |
C16—C17—C19—C20 | 2.0 (4) | N2—C6—N3—C7 | 0.4 (3) |
C18—C17—C19—C20 | −172.4 (2) | C5—C6—N3—C7 | −178.8 (3) |
C17—C19—C20—C14 | 1.3 (4) | N2—C6—N3—O2ii | −134.5 (2) |
C15—C14—C20—C19 | −3.1 (4) | C5—C6—N3—O2ii | 46.3 (4) |
C13—C14—C20—C19 | 171.6 (2) | N2—C6—N3—O4iii | 141.23 (18) |
O2—C13—O1—Co1 | 9.5 (2) | C5—C6—N3—O4iii | −38.0 (3) |
C14—C13—O1—Co1 | −167.6 (2) | C8—C7—N3—C6 | 179.9 (3) |
N2—Co1—O1—C13 | −18.8 (3) | C12—C7—N3—C6 | −0.1 (3) |
O4i—Co1—O1—C13 | 154.12 (15) | C8—C7—N3—O2ii | −26.5 (4) |
N1—Co1—O1—C13 | −97.02 (16) | C12—C7—N3—O2ii | 153.47 (18) |
O2—Co1—O1—C13 | −5.52 (14) | C8—C7—N3—O4iii | 50.0 (4) |
O3i—Co1—O1—C13 | 92.43 (16) | C12—C7—N3—O4iii | −130.1 (2) |
C18i—Co1—O1—C13 | 122.59 (16) |
Symmetry codes: (i) x−1, −y+1/2, z−1/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, y+1/2, −z+3/2; (iv) x+1, −y+1/2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3B···O2ii | 0.86 | 2.27 | 2.913 (3) | 132 |
N3—H3B···O4iii | 0.86 | 2.36 | 2.963 (3) | 127 |
Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) −x+1, y+1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | [Co(C8H4O4)(C12H9N3)] |
Mr | 418.26 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 7.2518 (7), 20.6995 (19), 11.3088 (11) |
β (°) | 95.914 (5) |
V (Å3) | 1688.5 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.05 |
Crystal size (mm) | 0.20 × 0.15 × 0.08 |
Data collection | |
Diffractometer | Rigaku CCD |
Absorption correction | Multi-scan (CrystalClear; Rigaku, 2002) |
Tmin, Tmax | 0.828, 0.923 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12922, 3866, 3170 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.100, 1.10 |
No. of reflections | 3866 |
No. of parameters | 253 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.40, −0.40 |
Computer programs: CrystalClear (Rigaku, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3B···O2i | 0.86 | 2.27 | 2.913 (3) | 132.1 |
N3—H3B···O4ii | 0.86 | 2.36 | 2.963 (3) | 127.1 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, y+1/2, −z+3/2. |
benzene-1,4-dicarboxylatic acid is often used to bridge metal atoms with 2,2'-bipyridine or 1,10-phenanthroline as auxiliary ligands (Sun et al., 2001; Zhang et al., 2003; Cano et al., 1997). Those compounds demonstrate various network topologies. In the title compound the CoII atom is six coordinated (Fig. 1), bonded to two nitrogen atoms of the chelating 2-(2-pyridyl)benzimidazole ligand, and bridged by the benzene-1,4-dicarboxylate into a zigzag chain (Fig. 2). The chains are further connected into a three-dimensional framework via intermolecular N—H···O hydrogen bonds as well as π-π interactions (perpendicular distance: 3.54 Å, centroid···centroid distances: 3.678Å and 3.697 Å) (Fig. 3).