Dibromido(6,6′-dimethyl-2,2′-bipyridine-κ2N,N′)cadmium

Shirvan, S.A.; Haydari Dezfuli, S.

doi:10.1107/S1600536812033648

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page m1143

doi:10.1107/S1600536812033648

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Dibromido(6,6′-dimethyl-2,2′-bipyridine-κ²N,N′)cadmium

Sadif A. Shirvan ^a ^* and Sara Haydari Dezfuli ^a

^aDepartment of Chemistry, Islamic Azad University, Omidieh Branch, Omidieh, Iran
^*Correspondence e-mail: sadif_shirvan1@yahoo.com

(Received 18 July 2012; accepted 25 July 2012; online 4 August 2012)

In the title compound, [CdBr₂(C₁₂H₁₂N₂)], the Cd^II atom is four-coordinated in a distorted tetrahedral geometry by two N atoms from a 6,6′-dimethyl-2,2′-bipyridine ligand and two terminal Br atoms. In the crystal, C—H⋯Br hydrogen bonds and π–π stacking interactions between the pyridine rings [centroid–centroid distance = 3.763 (5) Å] are present.

Related literature

For related structures, see: Akbarzadeh Torbati et al. (2010 ); Alizadeh et al. (2010 , 2011 ); Alizadeh, Kalateh, Ebadi et al. (2009 ); Alizadeh, Kalateh, Khoshtarkib et al. (2009 ); Alizadeh, Khoshtarkib et al. (2009 ); Itoh et al. (2005 ); Kou et al. (2008 ); Onggo et al. (2005 ); Shirvan & Haydari Dezfuli (2012a ,b ).

Experimental

Crystal data

[CdBr₂(C₁₂H₁₂N₂)]
M_r = 456.45
Monoclinic, P 2₁ /c
a = 7.7606 (11) Å
b = 10.3832 (17) Å
c = 18.184 (2) Å
β = 97.460 (11)°
V = 1452.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 6.98 mm⁻¹
T = 298 K
0.40 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.054, T_max = 0.155
11844 measured reflections
2862 independent reflections
1945 reflections with I > 2σ(I)
R_int = 0.098

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.124
S = 1.03
2862 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.78 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1C⋯Br1ⁱ	0.96	2.90	3.848 (10)	171
Symmetry code: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812033648/hy2576sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812033648/hy2576Isup2.hkl

checkCIF report

Comment top

Recently, we reported the synthesis and crystal structures of [Cd(5,5'-dmbpy)(µ-Br)₂]_n (Shirvan & Haydari Dezfuli, 2012a) and [CdBr₂(4,4'-dmbpy)(DMSO)] (Shirvan & Haydari Dezfuli, 2012b) (5,5'-dmbpy = 5,5'-dimethyl-2,2'-bipyridine, 4,4'-dmbpy = 4,4'-dimethyl-2,2'-bipyridine, DMSO = dimethyl sulfoxide). 6,6'-Dimethyl-2,2'-bipyridine (6,6'-dmbipy) is a good bidentate ligand and numerous complexes with 6,6'-dmbipy have been prepared, such as that of zinc (Alizadeh, Kalateh, Ebadi et al., 2009; Alizadeh, Kalateh, Khoshtarkib et al., 2009; Alizadeh, Khoshtarkib et al., 2009), copper (Itoh et al., 2005), cadmium (Alizadeh et al., 2010), cobalt (Akbarzadeh Torbati et al., 2010), nickel (Kou et al., 2008), ruthenium (Onggo et al., 2005) and mercury (Alizadeh et al., 2011). We report herein the synthesis and crystal structure of the title compound.

In the title compound (Fig. 1), the Cd^II atom is four-coordinated in a distorted tetrahedral geometry by two N atoms from a 6,6'-dimethyl-2,2'-bipyridine ligand and two terminal Br atoms. The crystal structure is stabilized by intermolecular C—H···Br hydrogen bonds (Table 1) and π–π contacts (Fig. 2) between the pyridine rings, Cg2···Cg3ⁱ [symmetry code: (i) -x, 1-y, -z. Cg2 and Cg3 are the centroids of the N1/C2–C6 ring and N2/C7–C11 ring], with a centroid–centroid distance of 3.763 (5) Å.

Related literature top

For related structures, see: Akbarzadeh Torbati et al. (2010); Alizadeh et al. (2010, 2011); Alizadeh, Kalateh, Ebadi et al. (2009); Alizadeh, Kalateh, Khoshtarkib et al. (2009); Alizadeh, Khoshtarkib et al. (2009); Itoh et al. (2005); Kou et al. (2008); Onggo et al. (2005); Shirvan & Haydari Dezfuli (2012a,b).

Experimental top

For the preparation of the title compound, a solution of 6,6'-dimethyl-2,2'-bipyridine (0.25 g, 1.33 mmol) in methanol (10 ml) was added to a solution of CdBr₂.4H₂O (0.46 g, 1.33 mmol) in methanol (10 ml) at room temperature. Crystals suitable for X-ray diffraction experiment were obtained by methanol diffusion into a colorless solution in DMSO after one week (yield: 0.47 g, 77.4%).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Crystal packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

Dibromido(6,6'-dimethyl-2,2'-bipyridine-κ²N,N')cadmium top

Crystal data top

[CdBr₂(C₁₂H₁₂N₂)]	F(000) = 864
M_r = 456.45	D_x = 2.087 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11844 reflections
a = 7.7606 (11) Å	θ = 2.3–26.0°
b = 10.3832 (17) Å	µ = 6.98 mm⁻¹
c = 18.184 (2) Å	T = 298 K
β = 97.460 (11)°	Block, colorless
V = 1452.8 (4) Å³	0.40 × 0.20 × 0.15 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2862 independent reflections
Radiation source: fine-focus sealed tube	1945 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.098
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
T_min = 0.054, T_max = 0.155	k = −12→12
11844 measured reflections	l = −19→22

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0602P)²] where P = (F_o² + 2F_c²)/3
2862 reflections	(Δ/σ)_max = 0.003
154 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −0.78 e Å⁻³

Crystal data top

[CdBr₂(C₁₂H₁₂N₂)]	V = 1452.8 (4) Å³
M_r = 456.45	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.7606 (11) Å	µ = 6.98 mm⁻¹
b = 10.3832 (17) Å	T = 298 K
c = 18.184 (2) Å	0.40 × 0.20 × 0.15 mm
β = 97.460 (11)°

Data collection top

Bruker APEXII CCD diffractometer	2862 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1945 reflections with I > 2σ(I)
T_min = 0.054, T_max = 0.155	R_int = 0.098
11844 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.03	Δρ_max = 0.61 e Å⁻³
2862 reflections	Δρ_min = −0.78 e Å⁻³
154 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
C1	0.1386 (14)	0.4345 (10)	0.2292 (5)	0.081 (3)
H1A	0.2494	0.3951	0.2444	0.098*
H1B	0.0530	0.3689	0.2161	0.098*
H1C	0.1055	0.4852	0.2693	0.098*
C2	0.1505 (10)	0.5178 (8)	0.1648 (5)	0.060 (2)
C3	0.1116 (12)	0.6486 (9)	0.1659 (6)	0.077 (3)
H3	0.0782	0.6861	0.2083	0.092*
C4	0.1230 (12)	0.7210 (8)	0.1044 (7)	0.078 (3)
H4	0.0963	0.8083	0.1044	0.094*
C5	0.1750 (11)	0.6642 (8)	0.0409 (6)	0.071 (3)
H5	0.1835	0.7133	−0.0013	0.085*
C6	0.2136 (9)	0.5334 (7)	0.0417 (4)	0.0483 (17)
C7	0.2699 (8)	0.4638 (7)	−0.0232 (4)	0.0461 (17)
C8	0.2878 (11)	0.5254 (9)	−0.0896 (5)	0.066 (2)
H8	0.2613	0.6124	−0.0958	0.079*
C9	0.3445 (11)	0.4568 (11)	−0.1454 (5)	0.072 (3)
H9	0.3569	0.4969	−0.1902	0.087*
C10	0.3835 (11)	0.3288 (11)	−0.1359 (5)	0.070 (3)
H10	0.4226	0.2818	−0.1740	0.084*
C11	0.3646 (10)	0.2703 (8)	−0.0699 (5)	0.0543 (19)
C12	0.4037 (14)	0.1324 (10)	−0.0560 (6)	0.080 (3)
H12A	0.3013	0.0891	−0.0446	0.095*
H12B	0.4944	0.1241	−0.0150	0.095*
H12C	0.4410	0.0945	−0.0995	0.095*
N1	0.1993 (7)	0.4635 (6)	0.1027 (3)	0.0470 (14)
N2	0.3092 (7)	0.3379 (6)	−0.0136 (3)	0.0448 (13)
Cd1	0.27194 (7)	0.25065 (5)	0.09801 (3)	0.04813 (18)
Br1	0.01860 (13)	0.10203 (9)	0.10288 (6)	0.0775 (3)
Br2	0.54796 (12)	0.18801 (10)	0.17765 (5)	0.0693 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.105 (7)	0.093 (7)	0.049 (5)	0.005 (6)	0.024 (5)	−0.017 (5)
C2	0.053 (5)	0.056 (5)	0.069 (6)	0.005 (4)	−0.001 (4)	−0.020 (4)
C3	0.074 (6)	0.058 (6)	0.095 (8)	0.011 (5)	−0.002 (5)	−0.019 (5)
C4	0.064 (5)	0.040 (5)	0.123 (9)	0.016 (4)	−0.022 (6)	−0.027 (5)
C5	0.063 (5)	0.042 (4)	0.099 (7)	−0.005 (4)	−0.023 (5)	0.011 (5)
C6	0.042 (4)	0.039 (4)	0.060 (5)	−0.002 (3)	−0.010 (3)	0.004 (3)
C7	0.039 (4)	0.049 (4)	0.048 (4)	−0.011 (3)	−0.003 (3)	0.011 (3)
C8	0.062 (5)	0.069 (6)	0.066 (6)	−0.011 (4)	0.002 (4)	0.023 (5)
C9	0.066 (5)	0.103 (8)	0.048 (5)	−0.017 (5)	0.006 (4)	0.020 (5)
C10	0.060 (5)	0.109 (8)	0.042 (4)	−0.019 (5)	0.007 (4)	−0.003 (5)
C11	0.055 (4)	0.060 (5)	0.048 (4)	−0.002 (4)	0.009 (4)	−0.005 (4)
C12	0.093 (7)	0.079 (7)	0.067 (6)	0.007 (5)	0.013 (5)	−0.019 (5)
N1	0.042 (3)	0.048 (3)	0.051 (4)	−0.001 (3)	0.002 (3)	−0.007 (3)
N2	0.047 (3)	0.046 (3)	0.041 (3)	−0.008 (3)	0.004 (3)	0.001 (3)
Cd1	0.0576 (3)	0.0421 (3)	0.0456 (3)	0.0049 (3)	0.0102 (2)	0.0069 (2)
Br1	0.0804 (6)	0.0631 (6)	0.0900 (7)	−0.0163 (5)	0.0155 (5)	0.0197 (5)
Br2	0.0661 (5)	0.0808 (6)	0.0597 (5)	0.0161 (5)	0.0033 (4)	0.0171 (5)

Geometric parameters (Å, º) top

C1—C2	1.469 (13)	C8—C9	1.358 (14)
C1—H1A	0.9600	C8—H8	0.9300
C1—H1B	0.9600	C9—C10	1.369 (15)
C1—H1C	0.9600	C9—H9	0.9300
C2—N1	1.360 (10)	C10—C11	1.369 (12)
C2—C3	1.392 (13)	C10—H10	0.9300
C3—C4	1.360 (15)	C11—N2	1.357 (10)
C3—H3	0.9300	C11—C12	1.479 (12)
C4—C5	1.402 (14)	C12—H12A	0.9600
C4—H4	0.9300	C12—H12B	0.9600
C5—C6	1.390 (11)	C12—H12C	0.9600
C5—H5	0.9300	N1—Cd1	2.285 (6)
C6—N1	1.341 (10)	N2—Cd1	2.274 (6)
C6—C7	1.498 (11)	Cd1—Br1	2.5099 (11)
C7—N2	1.349 (9)	Cd1—Br2	2.5106 (11)
C7—C8	1.389 (11)

C2—C1—H1A	109.5	C8—C9—C10	120.1 (8)
C2—C1—H1B	109.5	C8—C9—H9	119.9
H1A—C1—H1B	109.5	C10—C9—H9	119.9
C2—C1—H1C	109.5	C9—C10—C11	119.6 (9)
H1A—C1—H1C	109.5	C9—C10—H10	120.2
H1B—C1—H1C	109.5	C11—C10—H10	120.2
N1—C2—C3	120.1 (9)	N2—C11—C10	120.8 (8)
N1—C2—C1	118.2 (7)	N2—C11—C12	116.8 (7)
C3—C2—C1	121.8 (9)	C10—C11—C12	122.4 (8)
C4—C3—C2	119.3 (10)	C11—C12—H12A	109.5
C4—C3—H3	120.3	C11—C12—H12B	109.5
C2—C3—H3	120.3	H12A—C12—H12B	109.5
C3—C4—C5	120.1 (8)	C11—C12—H12C	109.5
C3—C4—H4	119.9	H12A—C12—H12C	109.5
C5—C4—H4	119.9	H12B—C12—H12C	109.5
C6—C5—C4	119.1 (9)	C6—N1—C2	121.6 (7)
C6—C5—H5	120.5	C6—N1—Cd1	116.5 (5)
C4—C5—H5	120.5	C2—N1—Cd1	121.9 (5)
N1—C6—C5	119.8 (8)	C7—N2—C11	119.4 (6)
N1—C6—C7	117.0 (6)	C7—N2—Cd1	116.7 (5)
C5—C6—C7	123.1 (8)	C11—N2—Cd1	123.8 (5)
N2—C7—C8	120.9 (7)	N2—Cd1—N1	73.0 (2)
N2—C7—C6	116.7 (6)	N2—Cd1—Br1	117.85 (15)
C8—C7—C6	122.4 (7)	N1—Cd1—Br1	113.28 (14)
C9—C8—C7	119.1 (9)	N2—Cd1—Br2	114.84 (15)
C9—C8—H8	120.4	N1—Cd1—Br2	115.17 (15)
C7—C8—H8	120.4	Br1—Cd1—Br2	115.72 (4)

N1—C2—C3—C4	0.0 (13)	C3—C2—N1—Cd1	178.3 (6)
C1—C2—C3—C4	−179.3 (9)	C1—C2—N1—Cd1	−2.4 (10)
C2—C3—C4—C5	−0.6 (15)	C8—C7—N2—C11	−0.9 (10)
C3—C4—C5—C6	0.3 (14)	C6—C7—N2—C11	−178.6 (7)
C4—C5—C6—N1	0.6 (12)	C8—C7—N2—Cd1	−179.7 (5)
C4—C5—C6—C7	179.9 (7)	C6—C7—N2—Cd1	2.6 (7)
N1—C6—C7—N2	−3.0 (9)	C10—C11—N2—C7	0.9 (11)
C5—C6—C7—N2	177.7 (7)	C12—C11—N2—C7	−179.4 (7)
N1—C6—C7—C8	179.3 (7)	C10—C11—N2—Cd1	179.7 (6)
C5—C6—C7—C8	0.0 (11)	C12—C11—N2—Cd1	−0.6 (10)
N2—C7—C8—C9	0.4 (12)	C7—N2—Cd1—N1	−1.2 (4)
C6—C7—C8—C9	178.0 (7)	C11—N2—Cd1—N1	180.0 (6)
C7—C8—C9—C10	−0.1 (13)	C7—N2—Cd1—Br1	106.6 (4)
C8—C9—C10—C11	0.2 (13)	C11—N2—Cd1—Br1	−72.2 (6)
C9—C10—C11—N2	−0.6 (13)	C7—N2—Cd1—Br2	−111.6 (4)
C9—C10—C11—C12	179.8 (8)	C11—N2—Cd1—Br2	69.6 (6)
C5—C6—N1—C2	−1.2 (11)	C6—N1—Cd1—N2	−0.5 (5)
C7—C6—N1—C2	179.4 (6)	C2—N1—Cd1—N2	−178.0 (6)
C5—C6—N1—Cd1	−178.8 (5)	C6—N1—Cd1—Br1	−114.1 (5)
C7—C6—N1—Cd1	1.9 (8)	C2—N1—Cd1—Br1	68.4 (6)
C3—C2—N1—C6	0.9 (11)	C6—N1—Cd1—Br2	109.5 (5)
C1—C2—N1—C6	−179.8 (8)	C2—N1—Cd1—Br2	−68.0 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1C···Br1ⁱ	0.96	2.90	3.848 (10)	171

Symmetry code: (i) −x, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[CdBr₂(C₁₂H₁₂N₂)]
M_r	456.45
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.7606 (11), 10.3832 (17), 18.184 (2)
β (°)	97.460 (11)
V (Å³)	1452.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	6.98
Crystal size (mm)	0.40 × 0.20 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.054, 0.155
No. of measured, independent and observed [I > 2σ(I)] reflections	11844, 2862, 1945
R_int	0.098
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.124, 1.03
No. of reflections	2862
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.78

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1C···Br1ⁱ	0.96	2.90	3.848 (10)	171

Symmetry code: (i) −x, y+1/2, −z+1/2.

Acknowledgements

We are grateful to the Islamic Azad University, Omidieh Branch, for financial support.

References

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