Abstract
In centrosymmetric dinuclear title compound, [Cd2Cl4(C18H16N2O2)2], the CdII atom is seven-coordinated in a pentagonal–bipyramidal environment defined by two N atoms and two O atoms from one ligand and three Cl− anions, two of which are bridging. A π–π interaction between adjacent pyridine rings [centroid–centroid distance = 3.773 (1) Å] further stablizes the dimer.
Related literature
For general background to flexible bipyridyl-based ligands, see: Wang et al. (2004) ▶; Oh et al. (2005) ▶. For the synthesis of the ligand, see: Liu et al. (2010a
▶,b
▶). For a related structure, see: Liu et al. (2011 ▶).
Experimental
Crystal data
[Cd2Cl4(C18H16N2O2)2]
M r = 951.26
Monoclinic,
a = 10.833 (2) Å
b = 10.968 (2) Å
c = 16.095 (3) Å
β = 109.14 (3)°
V = 1806.6 (6) Å3
Z = 2
Mo Kα radiation
μ = 1.52 mm−1
T = 293 K
0.23 × 0.22 × 0.20 mm
Data collection
Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.722, T max = 0.751
17295 measured reflections
4128 independent reflections
3686 reflections with I > 2σ(I)
R int = 0.021
Refinement
R[F 2 > 2σ(F 2)] = 0.019
wR(F 2) = 0.048
S = 1.05
4128 reflections
226 parameters
H-atom parameters constrained
Δρmax = 0.36 e Å−3
Δρmin = −0.24 e Å−3
Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ▶); 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.
Supplementary Material
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811037858/ng5223sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037858/ng5223Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Table 1. Selected bond lengths (Å).
| Cd1—N2 | 2.3920 (15) |
| Cd1—N1 | 2.3958 (15) |
| Cd1—Cl2 | 2.5103 (6) |
| Cd1—O1 | 2.6197 (14) |
| Cd1—Cl1 | 2.6197 (6) |
| Cd1—O2 | 2.6288 (14) |
| Cd1—Cl1i | 2.6873 (11) |
Symmetry code: (i)
.
Acknowledgments
The authors thank the Project of Innovation Service Platform of Heilongjiang Province (PG09J001) and Heilongjiang University for supporting this work.
supplementary crystallographic information
Comment
Aromatic molecules containing two pyridyl groups have been widely used as building blocks for new supramolecular architectures in recent years. Compared with rigid bridging ligands, flexible bipyridine ligands are able to generate some unusual frameworks (Wang et al., 2004; Oh et al., 2005). In continuation of previous works (Liu et al., 2010a; 2010b), we report the crystal structure of the title compound.
In centrosymmetric dinuclear [CdCl2(C18H16N2O2)]2, the CdII atom is seven-coordinated in a pentagonal bipyramidal environment defined by two N atoms and two O atoms from one ligand and three chlorides. Two of chlorides serve are bridging. A π—π interaction between adjacent pyridine rings [center to center distance 3.773?(1)?Å] further stablizes the dimer (Fig. 1, Table 1).
Experimental
The 1,2-bis(pyridin-2-ylmethoxy)benzene ligand was synthesized according to a literature method (Liu et al.,2010a). A solution of CdCl2.5H2O (0.2 mmol,0.0456 g) in water (2 ml) was added to a solution of the ligand (0.2 mmol, 0.0584 g) in 5 ml methanol under constant stirring; the solution was stirred for about 1 hour and then filted. The filtate was maintained for about one week under room temperature to give colorless block-like crystals.
Refinement
H atoms bound to C atoms were placed in calculated positions and treated as riding on their parent atoms, with C—H = 0.93 Å (aromatic); C—H = 0.97 Å (methylene), and with Uiso(H) = 1.2Ueq(C).
Figures
Fig. 1.
The molecular structure of the title compound, showing displacement ellipsoids at the 50% probability level for non-H atoms. Symmetry codes: (I) -x+1,-y+1,1-z.
Crystal data
| [Cd2Cl4(C18H16N2O2)2] | F(000) = 944 |
| Mr = 951.26 | Dx = 1.749 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 15418 reflections |
| a = 10.833 (2) Å | θ = 3.3–27.5° |
| b = 10.968 (2) Å | µ = 1.52 mm−1 |
| c = 16.095 (3) Å | T = 293 K |
| β = 109.14 (3)° | Bolck, colorless |
| V = 1806.6 (6) Å3 | 0.23 × 0.22 × 0.20 mm |
| Z = 2 |
Data collection
| Rigaku R-AXIS RAPID diffractometer | 4128 independent reflections |
| Radiation source: fine-focus sealed tube | 3686 reflections with I > 2σ(I) |
| graphite | Rint = 0.021 |
| ω scans | θmax = 27.5°, θmin = 3.3° |
| Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −14→13 |
| Tmin = 0.722, Tmax = 0.751 | k = −14→14 |
| 17295 measured reflections | l = −20→20 |
Refinement
| 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)] = 0.019 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.048 | H-atom parameters constrained |
| S = 1.05 | w = 1/[σ2(Fo2) + (0.0229P)2 + 0.5495P] where P = (Fo2 + 2Fc2)/3 |
| 4128 reflections | (Δ/σ)max = 0.002 |
| 226 parameters | Δρmax = 0.36 e Å−3 |
| 0 restraints | Δρmin = −0.24 e Å−3 |
Special details
| 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| C1 | 0.6708 (2) | 0.4345 (2) | 0.34515 (14) | 0.0565 (5) | |
| H1 | 0.5939 | 0.4787 | 0.3220 | 0.068* | |
| C2 | 0.7136 (2) | 0.3659 (3) | 0.28896 (15) | 0.0679 (7) | |
| H2 | 0.6668 | 0.3642 | 0.2291 | 0.081* | |
| C3 | 0.8267 (2) | 0.2998 (2) | 0.32244 (16) | 0.0660 (6) | |
| H3 | 0.8573 | 0.2515 | 0.2859 | 0.079* | |
| C4 | 0.8935 (2) | 0.3064 (2) | 0.41076 (15) | 0.0546 (5) | |
| H4 | 0.9708 | 0.2631 | 0.4350 | 0.065* | |
| C5 | 0.84454 (17) | 0.37838 (17) | 0.46357 (13) | 0.0406 (4) | |
| C6 | 0.9171 (2) | 0.3807 (2) | 0.55999 (13) | 0.0516 (5) | |
| H6A | 0.8960 | 0.3081 | 0.5870 | 0.062* | |
| H6B | 1.0103 | 0.3801 | 0.5696 | 0.062* | |
| C7 | 0.93736 (16) | 0.48931 (16) | 0.69088 (11) | 0.0376 (4) | |
| C8 | 1.0417 (2) | 0.41839 (18) | 0.73965 (14) | 0.0507 (5) | |
| H8 | 1.0810 | 0.3649 | 0.7111 | 0.061* | |
| C9 | 1.0880 (2) | 0.4263 (2) | 0.83053 (15) | 0.0565 (5) | |
| H9 | 1.1587 | 0.3788 | 0.8628 | 0.068* | |
| C10 | 1.0299 (2) | 0.5037 (2) | 0.87260 (13) | 0.0554 (5) | |
| H10 | 1.0605 | 0.5081 | 0.9337 | 0.066* | |
| C11 | 0.9252 (2) | 0.57610 (18) | 0.82491 (13) | 0.0473 (4) | |
| H11 | 0.8860 | 0.6286 | 0.8542 | 0.057* | |
| C12 | 0.87928 (17) | 0.57023 (15) | 0.73393 (12) | 0.0367 (4) | |
| C13 | 0.68776 (19) | 0.68425 (18) | 0.72191 (12) | 0.0440 (4) | |
| H13A | 0.7328 | 0.7322 | 0.7736 | 0.053* | |
| H13B | 0.6476 | 0.6149 | 0.7404 | 0.053* | |
| C14 | 0.58438 (17) | 0.76039 (16) | 0.65859 (12) | 0.0417 (4) | |
| C15 | 0.5092 (3) | 0.8376 (2) | 0.69083 (17) | 0.0681 (7) | |
| H15 | 0.5224 | 0.8415 | 0.7508 | 0.082* | |
| C16 | 0.4150 (3) | 0.9084 (2) | 0.6327 (2) | 0.0826 (9) | |
| H16 | 0.3629 | 0.9600 | 0.6529 | 0.099* | |
| C17 | 0.3989 (2) | 0.9021 (2) | 0.5454 (2) | 0.0685 (7) | |
| H17 | 0.3379 | 0.9513 | 0.5052 | 0.082* | |
| C18 | 0.4747 (2) | 0.82148 (18) | 0.51789 (16) | 0.0546 (5) | |
| H18 | 0.4632 | 0.8167 | 0.4581 | 0.066* | |
| Cd1 | 0.660311 (11) | 0.587855 (10) | 0.515336 (7) | 0.03233 (5) | |
| Cl1 | 0.57974 (4) | 0.42461 (4) | 0.60476 (3) | 0.03852 (9) | |
| Cl2 | 0.76064 (5) | 0.75247 (5) | 0.44987 (3) | 0.05070 (12) | |
| N1 | 0.73405 (15) | 0.44122 (14) | 0.43174 (10) | 0.0401 (3) | |
| N2 | 0.56444 (15) | 0.74944 (13) | 0.57321 (10) | 0.0410 (3) | |
| O1 | 0.88495 (11) | 0.48583 (11) | 0.60035 (8) | 0.0393 (3) | |
| O2 | 0.77949 (11) | 0.64229 (11) | 0.68148 (8) | 0.0375 (3) |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0481 (11) | 0.0767 (15) | 0.0439 (11) | 0.0117 (11) | 0.0142 (9) | −0.0047 (10) |
| C2 | 0.0637 (14) | 0.0959 (18) | 0.0434 (12) | 0.0060 (14) | 0.0166 (10) | −0.0174 (12) |
| C3 | 0.0620 (13) | 0.0842 (17) | 0.0582 (13) | 0.0049 (13) | 0.0282 (11) | −0.0254 (12) |
| C4 | 0.0476 (11) | 0.0610 (12) | 0.0578 (12) | 0.0089 (10) | 0.0210 (10) | −0.0143 (10) |
| C5 | 0.0395 (9) | 0.0410 (9) | 0.0452 (10) | −0.0007 (8) | 0.0190 (8) | −0.0059 (8) |
| C6 | 0.0551 (12) | 0.0526 (11) | 0.0460 (11) | 0.0186 (10) | 0.0150 (9) | −0.0048 (9) |
| C7 | 0.0344 (8) | 0.0401 (9) | 0.0367 (9) | −0.0027 (7) | 0.0097 (7) | 0.0005 (7) |
| C8 | 0.0434 (10) | 0.0517 (11) | 0.0524 (11) | 0.0103 (9) | 0.0095 (9) | 0.0008 (9) |
| C9 | 0.0483 (11) | 0.0593 (13) | 0.0507 (12) | 0.0091 (10) | 0.0012 (9) | 0.0092 (10) |
| C10 | 0.0581 (12) | 0.0618 (13) | 0.0368 (10) | −0.0025 (11) | 0.0027 (9) | 0.0034 (9) |
| C11 | 0.0530 (11) | 0.0480 (10) | 0.0374 (9) | −0.0011 (9) | 0.0099 (8) | −0.0043 (8) |
| C12 | 0.0348 (8) | 0.0355 (8) | 0.0373 (9) | −0.0031 (7) | 0.0085 (7) | 0.0007 (7) |
| C13 | 0.0471 (10) | 0.0507 (10) | 0.0361 (9) | 0.0023 (9) | 0.0160 (8) | −0.0081 (8) |
| C14 | 0.0413 (9) | 0.0377 (9) | 0.0487 (10) | −0.0033 (8) | 0.0184 (8) | −0.0117 (8) |
| C15 | 0.0770 (16) | 0.0662 (14) | 0.0667 (15) | 0.0145 (13) | 0.0311 (13) | −0.0216 (12) |
| C16 | 0.0782 (18) | 0.0681 (16) | 0.104 (2) | 0.0297 (14) | 0.0327 (17) | −0.0219 (15) |
| C17 | 0.0594 (14) | 0.0456 (12) | 0.0910 (19) | 0.0189 (11) | 0.0119 (13) | −0.0043 (12) |
| C18 | 0.0595 (12) | 0.0414 (10) | 0.0585 (12) | 0.0116 (10) | 0.0132 (10) | 0.0016 (9) |
| Cd1 | 0.03316 (7) | 0.03389 (7) | 0.03234 (7) | 0.00016 (5) | 0.01399 (5) | 0.00062 (5) |
| Cl1 | 0.0354 (2) | 0.0422 (2) | 0.0366 (2) | −0.00347 (17) | 0.00993 (16) | 0.00500 (17) |
| Cl2 | 0.0531 (3) | 0.0566 (3) | 0.0449 (2) | −0.0115 (2) | 0.0195 (2) | 0.0106 (2) |
| N1 | 0.0396 (8) | 0.0453 (8) | 0.0383 (8) | 0.0041 (7) | 0.0168 (6) | −0.0027 (6) |
| N2 | 0.0439 (8) | 0.0360 (7) | 0.0436 (8) | 0.0059 (7) | 0.0148 (7) | −0.0010 (6) |
| O1 | 0.0369 (6) | 0.0421 (6) | 0.0380 (6) | 0.0080 (5) | 0.0109 (5) | −0.0019 (5) |
| O2 | 0.0389 (6) | 0.0393 (6) | 0.0345 (6) | 0.0039 (5) | 0.0124 (5) | −0.0020 (5) |
Geometric parameters (Å, °)
| C1—N1 | 1.338 (3) | C11—H11 | 0.9300 |
| C1—C2 | 1.368 (3) | C12—O2 | 1.381 (2) |
| C1—H1 | 0.9300 | C13—O2 | 1.431 (2) |
| C2—C3 | 1.373 (3) | C13—C14 | 1.497 (3) |
| C2—H2 | 0.9300 | C13—H13A | 0.9700 |
| C3—C4 | 1.369 (3) | C13—H13B | 0.9700 |
| C3—H3 | 0.9300 | C14—N2 | 1.325 (2) |
| C4—C5 | 1.387 (3) | C14—C15 | 1.388 (3) |
| C4—H4 | 0.9300 | C15—C16 | 1.376 (4) |
| C5—N1 | 1.330 (2) | C15—H15 | 0.9300 |
| C5—C6 | 1.492 (3) | C16—C17 | 1.360 (4) |
| C6—O1 | 1.422 (2) | C16—H16 | 0.9300 |
| C6—H6A | 0.9700 | C17—C18 | 1.376 (3) |
| C6—H6B | 0.9700 | C17—H17 | 0.9300 |
| C7—O1 | 1.380 (2) | C18—N2 | 1.339 (3) |
| C7—C8 | 1.385 (3) | C18—H18 | 0.9300 |
| C7—C12 | 1.396 (2) | Cd1—N2 | 2.3920 (15) |
| C8—C9 | 1.385 (3) | Cd1—N1 | 2.3958 (15) |
| C8—H8 | 0.9300 | Cd1—Cl2 | 2.5103 (6) |
| C9—C10 | 1.362 (3) | Cd1—O1 | 2.6197 (14) |
| C9—H9 | 0.9300 | Cd1—Cl1 | 2.6197 (6) |
| C10—C11 | 1.391 (3) | Cd1—O2 | 2.6288 (14) |
| C10—H10 | 0.9300 | Cd1—Cl1i | 2.6873 (11) |
| C11—C12 | 1.385 (3) | Cl1—Cd1i | 2.6873 (11) |
| N1—C1—C2 | 123.4 (2) | C15—C14—C13 | 119.04 (19) |
| N1—C1—H1 | 118.3 | C16—C15—C14 | 119.0 (2) |
| C2—C1—H1 | 118.3 | C16—C15—H15 | 120.5 |
| C1—C2—C3 | 118.9 (2) | C14—C15—H15 | 120.5 |
| C1—C2—H2 | 120.6 | C17—C16—C15 | 119.3 (2) |
| C3—C2—H2 | 120.6 | C17—C16—H16 | 120.3 |
| C4—C3—C2 | 118.7 (2) | C15—C16—H16 | 120.3 |
| C4—C3—H3 | 120.7 | C16—C17—C18 | 118.5 (2) |
| C2—C3—H3 | 120.7 | C16—C17—H17 | 120.8 |
| C3—C4—C5 | 119.2 (2) | C18—C17—H17 | 120.8 |
| C3—C4—H4 | 120.4 | N2—C18—C17 | 123.0 (2) |
| C5—C4—H4 | 120.4 | N2—C18—H18 | 118.5 |
| N1—C5—C4 | 122.40 (18) | C17—C18—H18 | 118.5 |
| N1—C5—C6 | 119.51 (16) | N2—Cd1—N1 | 169.53 (5) |
| C4—C5—C6 | 118.06 (17) | N2—Cd1—Cl2 | 86.19 (4) |
| O1—C6—C5 | 111.39 (16) | N1—Cd1—Cl2 | 88.69 (4) |
| O1—C6—H6A | 109.3 | N2—Cd1—O1 | 124.10 (5) |
| C5—C6—H6A | 109.3 | N1—Cd1—O1 | 65.35 (5) |
| O1—C6—H6B | 109.3 | Cl2—Cd1—O1 | 94.05 (3) |
| C5—C6—H6B | 109.3 | N2—Cd1—Cl1 | 91.55 (4) |
| H6A—C6—H6B | 108.0 | N1—Cd1—Cl1 | 94.72 (4) |
| O1—C7—C8 | 124.05 (17) | Cl2—Cd1—Cl1 | 171.978 (16) |
| O1—C7—C12 | 116.44 (15) | O1—Cd1—Cl1 | 80.84 (3) |
| C8—C7—C12 | 119.51 (17) | N2—Cd1—O2 | 64.32 (5) |
| C7—C8—C9 | 120.6 (2) | N1—Cd1—O2 | 125.51 (5) |
| C7—C8—H8 | 119.7 | Cl2—Cd1—O2 | 97.34 (3) |
| C9—C8—H8 | 119.7 | O1—Cd1—O2 | 60.22 (4) |
| C10—C9—C8 | 119.8 (2) | Cl1—Cd1—O2 | 74.77 (3) |
| C10—C9—H9 | 120.1 | N2—Cd1—Cl1i | 82.91 (4) |
| C8—C9—H9 | 120.1 | N1—Cd1—Cl1i | 89.09 (4) |
| C9—C10—C11 | 120.51 (19) | Cl2—Cd1—Cl1i | 100.64 (2) |
| C9—C10—H10 | 119.7 | O1—Cd1—Cl1i | 150.24 (3) |
| C11—C10—H10 | 119.7 | Cl1—Cd1—Cl1i | 86.69 (2) |
| C12—C11—C10 | 120.13 (19) | O2—Cd1—Cl1i | 141.26 (3) |
| C12—C11—H11 | 119.9 | Cd1—Cl1—Cd1i | 93.31 (2) |
| C10—C11—H11 | 119.9 | C5—N1—C1 | 117.47 (16) |
| O2—C12—C11 | 123.89 (16) | C5—N1—Cd1 | 123.73 (12) |
| O2—C12—C7 | 116.75 (15) | C1—N1—Cd1 | 118.10 (13) |
| C11—C12—C7 | 119.34 (17) | C14—N2—C18 | 118.17 (17) |
| O2—C13—C14 | 110.24 (15) | C14—N2—Cd1 | 121.82 (12) |
| O2—C13—H13A | 109.6 | C18—N2—Cd1 | 119.42 (13) |
| C14—C13—H13A | 109.6 | C7—O1—C6 | 115.30 (14) |
| O2—C13—H13B | 109.6 | C7—O1—Cd1 | 121.99 (10) |
| C14—C13—H13B | 109.6 | C6—O1—Cd1 | 115.63 (11) |
| H13A—C13—H13B | 108.1 | C12—O2—C13 | 115.29 (13) |
| N2—C14—C15 | 121.80 (19) | C12—O2—Cd1 | 121.12 (10) |
| N2—C14—C13 | 119.12 (15) | C13—O2—Cd1 | 110.67 (10) |
Symmetry codes: (i) −x+1, −y+1, −z+1.
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5223).
References
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811037858/ng5223sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037858/ng5223Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report

