Dichlorido(6-methyl-2,2′-bipyridine-κ2N,N′)zinc(II)

Ahmadi, R.; Kalateh, K.; Ebadi, A.; Amani, V.; Khavasi, H.R.

doi:10.1107/S1600536808028894

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page m1266

doi:10.1107/S1600536808028894

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Dichlorido(6-methyl-2,2′-bipyridine-κ²N,N′)zinc(II)

Roya Ahmadi,^a Khadijeh Kalateh,^a Amin Ebadi,^b Vahid Amani ^a ^* and Hamid Reza Khavasi ^c

^aIslamic Azad University, Shahr-e-Rey Branch, Tehran, Iran, ^bDepartment of Chemistry, Islamic Azad University, Kazeroon Branch, Kazeroon, Fars, Iran, and ^cDepartment of Chemistry, Shahid Beheshti University, Tehran 1983963113, Iran
^*Correspondence e-mail: v_amani2002@yahoo.com

(Received 8 September 2008; accepted 9 September 2008; online 13 September 2008)

In the molecule of the title compound, [ZnCl₂(C₁₁H₁₀N₂)], the Zn^II atom is four-coordinated in a distorted tetrahedral configuration by two N atoms from the 6-methyl-2,2′-bipyridine ligand and by two Cl atoms. There are π–π contacts between the pyridine ring and the five-membered ring, and also between the pyridine rings, [centroid–centroid distances = 3.685 (3) and 3.757 (3) Å, respectively].

Related literature

For related literature, see: Ahmadi et al. (2008 ); Yousefi et al. (2008 ); Khan & Tuck (1984 ); Gruia et al. (2007 ); Kozhevnikov et al. (2006 ); Reimann et al. (1966 ); Preston & Kennard (1969 ); Liu et al. (2004 ); Khavasi et al. (2008 ); Khalighi et al. (2008 ); Steffen & Palenik (1976 , 1977 ); Qin et al. (1999 ); Lundberg (1966 ).

Experimental

Crystal data

[ZnCl₂(C₁₁H₁₀N₂)]
M_r = 306.50
Monoclinic, P 2₁ /n
a = 7.4674 (15) Å
b = 9.5105 (17) Å
c = 17.656 (4) Å
β = 96.551 (18)°
V = 1245.7 (4) Å³
Z = 4
Mo Kα radiation
μ = 2.37 mm⁻¹
T = 298 (2) K
0.30 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ) T_min = 0.668, T_max = 0.802
10401 measured reflections
3358 independent reflections
2576 reflections with I > 2σ(I)
R_int = 0.078

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.130
S = 1.17
3358 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 1.04 e Å⁻³
Δρ_min = −0.70 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Zn1—N1	2.066 (4)
Zn1—N2	2.053 (4)
Zn1—Cl1	2.2236 (15)
Zn1—Cl2	2.1995 (13)

N1—Zn1—Cl1	111.08 (11)
N2—Zn1—Cl1	109.16 (11)
Cl2—Zn1—Cl1	116.72 (5)
N1—Zn1—Cl2	116.84 (11)
N2—Zn1—Cl2	117.28 (10)
N2—Zn1—N1	80.31 (15)

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536808028894/hk2529sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808028894/hk2529Isup2.hkl

checkCIF report

Comment top

Recently, we reported the syntheses and crystal structures of [Cd(5,5'-dmbpy)(µ-Cl)₂]_n, (II), (Ahmadi et al., 2008) and [Hg(4,4'-dmbpy)I₂], (III), (Yousefi et al., 2008) [where 5,5'-dmbpy is 5,5'-dimethyl-2,2'-bipyridine and 4,4'-dmbpy is 4,4'-dimethyl-2,2'-bi- pyridine]. There are several Zn^II complexes, with formula, [ZnCl₂(N-N)], such as [ZnCl₂(bipy)], (IV), (Khan & Tuck, 1984), [ZnCl₂(biim)], (V), (Gruia et al., 2007), [ZnCl₂(phbipy)], (VI), (Kozhevnikov et al., 2006), [ZnCl₂(phen)], (VII), (Reimann et al., 1966), [ZnCl₂(dmphen)], (VIII), (Preston & Kennard, 1969), [ZnCl₂(dpdmbip)], (IX), (Liu et al., 2004), [ZnCl₂(dm4bt)], (X), (Khavasi et al., 2008) and [Zn(5,5'-dmbpy)Cl₂], (XI), (Khalighi et al., 2008) [where bipy is 2,2'-bipyridine, biim is 2,2'-biimidazole, phbipy is 5-phenyl-2,2'-bipyridine, phen is 1,10-phenanthroline, dmphen is 2,9-dimethyl-1,10-phenanthroline, dpdmbip is 4,4'-diphenyl-6,6'-dimethyl-2,2'-bipyrimidine and dm4bt is 2,2'-dimethyl-4,4'-bithiazole] have been synthesized and characterized by single-crystal X-ray diffraction methods.

There are several Zn^II complexes, with formula, [ZnCl₂L₂], such as [ZnCl₂(py)₂], (XII), (Steffen & Palenik, 1976), [ZnCl₂(4-cypy)₂], (XIII), (Steffen & Palenik, 1977), [ZnCl₂(2-ampy)₂], (XIV), (Qin et al., 1999) and [ZnCl₂(im)₂], (XV), (Lundberg, 1966) [where py is pyridine, 4-cypy is 4-cyanopyridine, 2-ampy is 2-aminopyridine and im is imidazole] have been synthesized and characterized by single-crystal X-ray diffraction methods. We report herein the synthesis and crystal structure of the title compound, (I).

In the title compound, (I), (Fig. 1), the Zn^II atom is four-coordinated in a distorted tetrahedral configuration by two N atoms from 6-methyl-2,2'-bi- pyridine and two Cl atoms. The Zn-Cl and Zn-N bond lengths and angles (Table 1) are within normal ranges, as in (IV), (VII), (X) and (XI).

In the crystal structure, the π—π contacts (Fig. 2) between the rings A (Zn1/N1/N2/C5/C6) and C (N2/C6-C10), and also between the pyridine rings B (N1/C1-C5) and C, Cg1···Cg3ⁱ and Cg2···Cg3ⁱⁱ [symmetry codes: (i) -x, -y, -z; (ii) 1 - x, -y, -z, where Cg1, Cg2 and Cg3 are the centroids of the rings A (Zn1/N1/N2/C5/C6), B (N1/C1-C5) and C (N2/C6-C10), respectively] may stabilize the structure, with centroid-centroid distances of 3.685 (3) Å and 3.757 (3) Å, respectively.

Related literature top

For related literature, see: Ahmadi et al. (2008); Yousefi et al. (2008); Khan & Tuck (1984); Gruia et al. (2007); Kozhevnikov et al. (2006); Reimann et al. (1966); Preston & Kennard (1969); Liu et al. (2004); Khavasi et al. (2008); Khalighi et al. (2008); Steffen & Palenik (1976, 1977); Qin et al. (1999); Lundberg (1966).

Experimental top

For the preparation of the title compound, (I), a solution of 6-methyl-2,2' -bipyridine (0.15 g, 0.88 mmol) in methanol (10 ml) was added to a solution of ZnCl₂ (0.12 g, 0.88 mmol) in acetonitrile (30 ml) and the resulting colorless solution was stirred for 20 min at at 313 K, and then it was left to evaporate slowly at room temperature. After one week, colorless block crystals of the title compound were isolated (yield; 0.19 g, 70.4%).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level.
	Fig. 2. A packing diagram of the title compound.

Dichlorido(6-methyl-2,2'-bipyridine-κ²N,N')zinc(II) top

Crystal data top

[ZnCl₂(C₁₁H₁₀N₂)]	F(000) = 616
M_r = 306.50	D_x = 1.634 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1987 reflections
a = 7.4674 (15) Å	θ = 2.3–29.2°
b = 9.5105 (17) Å	µ = 2.37 mm⁻¹
c = 17.656 (4) Å	T = 298 K
β = 96.551 (18)°	Block, colorless
V = 1245.7 (4) Å³	0.30 × 0.15 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3358 independent reflections
Radiation source: fine-focus sealed tube	2576 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.078
ϕ and ω scans	θ_max = 29.2°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −10→10
T_min = 0.668, T_max = 0.802	k = −12→13
10401 measured reflections	l = −24→24

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H-atom parameters constrained
S = 1.17	w = 1/[σ²(F_o²) + (0.0315P)² + 1.9318P] where P = (F_o² + 2F_c²)/3
3358 reflections	(Δ/σ)_max = 0.004
145 parameters	Δρ_max = 1.05 e Å⁻³
0 restraints	Δρ_min = −0.70 e Å⁻³

Crystal data top

[ZnCl₂(C₁₁H₁₀N₂)]	V = 1245.7 (4) Å³
M_r = 306.50	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.4674 (15) Å	µ = 2.37 mm⁻¹
b = 9.5105 (17) Å	T = 298 K
c = 17.656 (4) Å	0.30 × 0.15 × 0.10 mm
β = 96.551 (18)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3358 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	2576 reflections with I > 2σ(I)
T_min = 0.668, T_max = 0.802	R_int = 0.078
10401 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.17	Δρ_max = 1.05 e Å⁻³
3358 reflections	Δρ_min = −0.70 e Å⁻³
145 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Zn1	0.26730 (7)	0.26879 (5)	0.08829 (3)	0.04730 (16)
Cl1	0.53626 (17)	0.30874 (16)	0.15251 (8)	0.0708 (4)
Cl2	0.04386 (18)	0.40228 (15)	0.11668 (9)	0.0701 (4)
N1	0.2881 (5)	0.2367 (4)	−0.0261 (2)	0.0494 (8)
N2	0.2225 (5)	0.0559 (4)	0.0820 (2)	0.0460 (8)
C1	0.3141 (7)	0.3363 (6)	−0.0782 (3)	0.0619 (12)
H1	0.3145	0.4304	−0.0639	0.074*
C2	0.3400 (8)	0.3028 (7)	−0.1517 (3)	0.0741 (16)
H2	0.3573	0.3733	−0.1867	0.089*
C3	0.3401 (8)	0.1653 (7)	−0.1730 (3)	0.0726 (16)
H3	0.3590	0.1414	−0.2226	0.087*
C4	0.3121 (6)	0.0608 (6)	−0.1210 (3)	0.0626 (13)
H4	0.3120	−0.0335	−0.1350	0.075*
C5	0.2840 (5)	0.1004 (5)	−0.0466 (2)	0.0465 (9)
C6	0.2434 (5)	−0.0003 (5)	0.0127 (3)	0.0469 (9)
C7	0.2248 (7)	−0.1435 (5)	0.0005 (3)	0.0606 (12)
H7	0.2412	−0.1824	−0.0465	0.073*
C8	0.1819 (7)	−0.2268 (6)	0.0589 (4)	0.0698 (15)
H8	0.1668	−0.3230	0.0512	0.084*
C9	0.1608 (7)	−0.1700 (6)	0.1293 (4)	0.0679 (14)
H9	0.1323	−0.2268	0.1692	0.082*
C10	0.1834 (6)	−0.0254 (5)	0.1392 (3)	0.0566 (11)
C11	0.1652 (11)	0.0450 (7)	0.2132 (3)	0.091 (2)
H11A	0.0699	0.1132	0.2063	0.109*
H11B	0.2763	0.0912	0.2311	0.109*
H11C	0.1376	−0.0239	0.2498	0.109*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0498 (3)	0.0446 (3)	0.0483 (3)	−0.0009 (2)	0.0092 (2)	−0.0117 (2)
Cl1	0.0512 (6)	0.0826 (9)	0.0770 (9)	0.0013 (6)	0.0008 (6)	−0.0358 (7)
Cl2	0.0599 (7)	0.0712 (8)	0.0801 (9)	0.0137 (6)	0.0111 (6)	−0.0207 (7)
N1	0.0449 (18)	0.056 (2)	0.0475 (19)	0.0037 (16)	0.0055 (15)	−0.0037 (17)
N2	0.0411 (18)	0.0465 (18)	0.050 (2)	−0.0016 (14)	0.0053 (15)	−0.0024 (15)
C1	0.060 (3)	0.068 (3)	0.059 (3)	0.005 (2)	0.012 (2)	0.007 (2)
C2	0.078 (4)	0.096 (5)	0.051 (3)	0.004 (3)	0.015 (3)	0.010 (3)
C3	0.068 (3)	0.107 (5)	0.044 (3)	0.010 (3)	0.011 (2)	−0.004 (3)
C4	0.052 (3)	0.077 (3)	0.056 (3)	0.014 (2)	−0.001 (2)	−0.023 (3)
C5	0.0370 (19)	0.058 (2)	0.043 (2)	0.0091 (18)	−0.0018 (16)	−0.0112 (18)
C6	0.0346 (19)	0.048 (2)	0.056 (2)	0.0026 (17)	−0.0032 (17)	−0.0144 (19)
C7	0.057 (3)	0.049 (3)	0.074 (3)	0.001 (2)	0.004 (2)	−0.014 (2)
C8	0.058 (3)	0.043 (2)	0.106 (4)	0.000 (2)	0.001 (3)	−0.009 (3)
C9	0.057 (3)	0.058 (3)	0.088 (4)	−0.003 (2)	0.003 (3)	0.022 (3)
C10	0.050 (2)	0.060 (3)	0.059 (3)	0.002 (2)	0.003 (2)	0.002 (2)
C11	0.129 (6)	0.093 (5)	0.053 (3)	−0.010 (4)	0.025 (4)	0.013 (3)

Geometric parameters (Å, º) top

Zn1—N1	2.066 (4)	C5—C6	1.475 (7)
Zn1—N2	2.053 (4)	C6—N2	1.360 (5)
Zn1—Cl1	2.2236 (15)	C6—C7	1.384 (6)
Zn1—Cl2	2.1995 (13)	C7—C8	1.367 (8)
C1—N1	1.350 (6)	C7—H7	0.9300
C1—C2	1.371 (7)	C8—C9	1.381 (8)
C1—H1	0.9300	C8—H8	0.9300
C2—C3	1.361 (9)	C9—C10	1.394 (7)
C2—H2	0.9300	C9—H9	0.9300
C3—C4	1.385 (8)	C10—N2	1.329 (6)
C3—H3	0.9300	C10—C11	1.488 (8)
C4—C5	1.406 (6)	C11—H11A	0.9600
C4—H4	0.9300	C11—H11B	0.9600
C5—N1	1.345 (6)	C11—H11C	0.9600

N1—Zn1—Cl1	111.08 (11)	N1—C5—C4	120.5 (5)
N2—Zn1—Cl1	109.16 (11)	N1—C5—C6	115.8 (4)
Cl2—Zn1—Cl1	116.72 (5)	C4—C5—C6	123.7 (4)
N1—Zn1—Cl2	116.84 (11)	N2—C6—C7	120.5 (5)
N2—Zn1—Cl2	117.28 (10)	N2—C6—C5	115.9 (4)
N2—Zn1—N1	80.31 (15)	C7—C6—C5	123.6 (4)
C1—N1—Zn1	126.6 (3)	C8—C7—C6	118.7 (5)
C5—N1—Zn1	113.8 (3)	C8—C7—H7	120.6
C5—N1—C1	119.6 (4)	C6—C7—H7	120.6
C6—N2—Zn1	113.6 (3)	C7—C8—C9	120.9 (5)
C10—N2—Zn1	125.5 (3)	C7—C8—H8	119.5
C10—N2—C6	120.8 (4)	C9—C8—H8	119.5
N1—C1—C2	121.9 (5)	C8—C9—C10	118.2 (5)
N1—C1—H1	119.0	C8—C9—H9	120.9
C2—C1—H1	119.0	C10—C9—H9	120.9
C3—C2—C1	119.3 (5)	N2—C10—C9	120.9 (5)
C3—C2—H2	120.3	N2—C10—C11	117.1 (5)
C1—C2—H2	120.3	C9—C10—C11	122.1 (5)
C2—C3—C4	120.1 (5)	C10—C11—H11A	109.5
C2—C3—H3	120.0	C10—C11—H11B	109.5
C4—C3—H3	120.0	H11A—C11—H11B	109.5
C3—C4—C5	118.5 (5)	C10—C11—H11C	109.5
C3—C4—H4	120.7	H11A—C11—H11C	109.5
C5—C4—H4	120.7	H11B—C11—H11C	109.5

N2—Zn1—N1—C5	−6.9 (3)	C6—C5—N1—Zn1	7.2 (5)
Cl2—Zn1—N1—C5	−122.7 (3)	C6—C5—N1—C1	−176.3 (4)
Cl1—Zn1—N1—C5	100.0 (3)	N1—C5—C6—N2	−2.7 (5)
N2—Zn1—N1—C1	176.9 (4)	C4—C5—C6—N2	179.1 (4)
Cl2—Zn1—N1—C1	61.1 (4)	N1—C5—C6—C7	176.6 (4)
Cl1—Zn1—N1—C1	−76.2 (4)	C4—C5—C6—C7	−1.6 (7)
Cl1—Zn1—N2—C10	73.8 (4)	C5—C6—N2—Zn1	−3.3 (4)
Cl2—Zn1—N2—C10	−61.8 (4)	C5—C6—N2—C10	179.1 (4)
N1—Zn1—N2—C10	−177.1 (4)	C7—C6—N2—Zn1	177.4 (3)
Cl1—Zn1—N2—C6	−103.7 (3)	C7—C6—N2—C10	−0.2 (6)
Cl2—Zn1—N2—C6	120.7 (3)	N2—C6—C7—C8	1.2 (7)
N1—Zn1—N2—C6	5.4 (3)	C5—C6—C7—C8	−178.1 (4)
C2—C1—N1—C5	−1.2 (7)	C6—C7—C8—C9	−1.2 (8)
C2—C1—N1—Zn1	174.8 (4)	C7—C8—C9—C10	0.3 (8)
N1—C1—C2—C3	−0.2 (9)	C8—C9—C10—N2	0.7 (8)
C1—C2—C3—C4	0.8 (9)	C8—C9—C10—C11	−179.4 (6)
C2—C3—C4—C5	0.0 (8)	C9—C10—N2—Zn1	−178.0 (4)
C3—C4—C5—N1	−1.4 (7)	C9—C10—N2—C6	−0.7 (7)
C3—C4—C5—C6	176.7 (4)	C11—C10—N2—Zn1	2.0 (6)
C4—C5—N1—Zn1	−174.5 (3)	C11—C10—N2—C6	179.3 (5)
C4—C5—N1—C1	2.0 (6)

Experimental details

Crystal data
Chemical formula	[ZnCl₂(C₁₁H₁₀N₂)]
M_r	306.50
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.4674 (15), 9.5105 (17), 17.656 (4)
β (°)	96.551 (18)
V (Å³)	1245.7 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.37
Crystal size (mm)	0.30 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1998)
T_min, T_max	0.668, 0.802
No. of measured, independent and observed [I > 2σ(I)] reflections	10401, 3358, 2576
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.687

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.130, 1.17
No. of reflections	3358
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.05, −0.70

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

Zn1—N1	2.066 (4)	Zn1—Cl1	2.2236 (15)
Zn1—N2	2.053 (4)	Zn1—Cl2	2.1995 (13)

N1—Zn1—Cl1	111.08 (11)	N1—Zn1—Cl2	116.84 (11)
N2—Zn1—Cl1	109.16 (11)	N2—Zn1—Cl2	117.28 (10)
Cl2—Zn1—Cl1	116.72 (5)	N2—Zn1—N1	80.31 (15)

Acknowledgements

We are grateful to the Islamic Azad University, Shahr-e-Rey Branch, for financial support.

References

Ahmadi, R., Khalighi, A., Kalateh, K., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1233. Web of Science CSD CrossRef IUCr Journals Google Scholar
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