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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Sep 30;67(Pt 10):m1415. doi: 10.1107/S1600536811037858

Di-μ-chlorido-bis­{[1,2-bis­(pyridin-2-ylmeth­oxy)benzene-κ4 N,O,O′,N′]chloridocadmium}

Jin-Sheng Gao a,b,*, Ying-Hui Yu a,b, Ying Liu b, Guang-Feng Hou a,b
PMCID: PMC3201405  PMID: 22064381

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).graphic file with name e-67-m1415-scheme1.jpg

Experimental

Crystal data

  • [Cd2Cl4(C18H16N2O2)2]

  • M r = 951.26

  • Monoclinic, Inline graphic

  • 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

e-67-m1415-sup1.cif (24.8KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037858/ng5223Isup2.hkl

e-67-m1415-Isup2.hkl (202.3KB, 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) Inline graphic.

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.

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 m3
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 mm1
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 Å3
0 restraints Δρmin = −0.24 e Å3

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

e-67-m1415-sup1.cif (24.8KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037858/ng5223Isup2.hkl

e-67-m1415-Isup2.hkl (202.3KB, hkl)

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


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