Di-μ-chlorido-bis­{[1,2-bis­(pyridin-2-ylmeth­oxy)benzene-κ4N,O,O′,N′]chloridocadmium}

Gao, J.-S.; Yu, Y.-H.; Liu, Y.; Hou, G.-F.

doi:10.1107/S1600536811037858

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page m1415

https://doi.org/10.1107/S1600536811037858

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Di-μ-chlorido-bis{[1,2-bis(pyridin-2-ylmethoxy)benzene-κ⁴N,O,O′,N′]chloridocadmium}

Jin-Sheng Gao,^a,^b ^* Ying-Hui Yu,^a,^b Ying Liu ^b and Guang-Feng Hou ^a,^b

^aEngineering Research Center of Pesticides of Heilongjiang University, Heilongjiang University, Harbin 150050, People's Republic of China, and ^bCollege of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China
^*Correspondence e-mail: hgf1000@163.com

(Received 2 September 2011; accepted 16 September 2011; online 30 September 2011)

In centrosymmetric dinuclear title compound, [Cd₂Cl₄(C₁₈H₁₆N₂O₂)₂], the Cd^II 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, P 2₁ /c
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[F² > 2σ(F²)] = 0.019
wR(F²) = 0.048
S = 1.05
4128 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.24 e Å⁻³

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) -x+1, -y+1, -z+1.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811037858/ng5223sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811037858/ng5223Isup2.hkl

checkCIF report

Comment top

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).

Related literature top

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 top

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.

Structure description top

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).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); 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 (Sheldrick, 2008).

Figures top

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.

Di-µ-chlorido-bis{[1,2-bis(pyridin-2-ylmethoxy)benzene- κ⁴N,O,O',N']chloridocadmium} top

Crystal data top

[Cd₂Cl₄(C₁₈H₁₆N₂O₂)₂]	F(000) = 944
M_r = 951.26	D_x = 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 top

Rigaku R-AXIS RAPID diffractometer	4128 independent reflections
Radiation source: fine-focus sealed tube	3686 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω scans	θ_max = 27.5°, θ_min = 3.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −14→13
T_min = 0.722, T_max = 0.751	k = −14→14
17295 measured reflections	l = −20→20

Refinement top

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(F_o²) + (0.0229P)² + 0.5495P] where P = (F_o² + 2F_c²)/3
4128 reflections	(Δ/σ)_max = 0.002
226 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

[Cd₂Cl₄(C₁₈H₁₆N₂O₂)₂]	V = 1806.6 (6) Å³
M_r = 951.26	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.833 (2) Å	µ = 1.52 mm⁻¹
b = 10.968 (2) Å	T = 293 K
c = 16.095 (3) Å	0.23 × 0.22 × 0.20 mm
β = 109.14 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4128 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3686 reflections with I > 2σ(I)
T_min = 0.722, T_max = 0.751	R_int = 0.021
17295 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.019	0 restraints
wR(F²) = 0.048	H-atom parameters constrained
S = 1.05	Δρ_max = 0.36 e Å⁻³
4128 reflections	Δρ_min = −0.24 e Å⁻³
226 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
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) top

	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, º) top

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 code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Cd₂Cl₄(C₁₈H₁₆N₂O₂)₂]
M_r	951.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.833 (2), 10.968 (2), 16.095 (3)
β (°)	109.14 (3)
V (Å³)	1806.6 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.52
Crystal size (mm)	0.23 × 0.22 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.722, 0.751
No. of measured, independent and observed [I > 2σ(I)] reflections	17295, 4128, 3686
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.019, 0.048, 1.05
No. of reflections	4128
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.24

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cd1—N2	2.3920 (15)	Cd1—Cl1	2.6197 (6)
Cd1—N1	2.3958 (15)	Cd1—O2	2.6288 (14)
Cd1—Cl2	2.5103 (6)	Cd1—Cl1ⁱ	2.6873 (11)
Cd1—O1	2.6197 (14)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The authors thank the Project of Innovation Service Platform of Heilongjiang Province (PG09J001) and Heilongjiang University for supporting this work.

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