metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

catena-Poly[[(5,5′-di­methyl-2,2′-bi­pyridine-κ2N,N′)cadmium]-di-μ-bromido]

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

(Received 21 May 2012; accepted 25 May 2012; online 31 May 2012)

In the crystal of the title polymeric compound, [CdBr2(C12H12N2)]n, the CdII cation is located on a twofold rotation axis. The CdII cation is six-coordinated in a distorted octa­hedral geometry formed by two N atoms from the 5,5′-dimethyl-2,2′-bipyridine ligand and four bridging Br anions. The bridging function of the Br anions leads to a polymeric chain running along the c axis.

Related literature

For related structures, see: Ahmadi et al. (2008[Ahmadi, R., Khalighi, A., Kalateh, K., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1233.], 2010[Ahmadi, R., Kalateh, K. & Amani, V. (2010). Acta Cryst. E66, m562.]); Albada et al. (2004[Albada, G. A., Mohamadou, A., Mutikainen, I., Turpeinen, U. & Reedijk, J. (2004). Eur. J. Inorg. Chem. pp. 3733-3742.]); Amani et al. (2007[Amani, V., Safari, N. & Khavasi, H. R. (2007). Polyhedron, 26, 4257-4262.], 2009[Amani, V., Safari, N., Khavasi, H. R. & Akkurt, M. (2009). Polyhedron, 28, 3026-3030.]); Han et al. (2006[Han, J., Fang, J., Dong, Y. & Chang, H. (2006). Acta Cryst. E62, m183-m184.]); Kalateh et al. (2010[Kalateh, K., Ahmadi, R. & Amani, V. (2010). Acta Cryst. E66, m512.]); Karaca et al. (2009[Karaca, S., Akkurt, M., Safari, N., Amani, V., Büyükgüngör, O. & Abedi, A. (2009). Acta Cryst. E65, m335-m336.]); Khalighi et al. (2008[Khalighi, A., Ahmadi, R., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1211-m1212.]); Maheshwari et al. (2007[Maheshwari, V., Carlone, M., Fronczek, F. R. & Marzilli, L. G. (2007). Acta Cryst. B63, 603-611.]); Tadayon Pour et al. (2008[Tadayon Pour, N., Ebadi, A., Abedi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1305.]); Zhang (2007[Zhang, B.-S. (2007). Acta Cryst. E63, m1562.]).

[Scheme 1]

Experimental

Crystal data
  • [CdBr2(C12H12N2)]

  • Mr = 456.45

  • Monoclinic, C 2/c

  • a = 19.637 (5) Å

  • b = 9.6563 (15) Å

  • c = 7.485 (2) Å

  • β = 104.76 (2)°

  • V = 1372.4 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 7.39 mm−1

  • T = 298 K

  • 0.12 × 0.11 × 0.09 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.435, Tmax = 0.548

  • 5378 measured reflections

  • 1346 independent reflections

  • 1015 reflections with I > 2σ(I)

  • Rint = 0.110

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.091

  • S = 1.03

  • 1346 reflections

  • 78 parameters

  • H-atom parameters constrained

  • Δρmax = 0.85 e Å−3

  • Δρmin = −0.70 e Å−3

Table 1
Selected bond lengths (Å)

Cd1—N1 2.352 (4)
Cd1—Br1 2.6676 (8)
Cd1—Br1i 2.9351 (10)
Symmetry code: (i) [x, -y, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

5,5'-Dimethyl-2,2'-bipyridine (5,5'-dmbipy), is a good bidentate ligand, and numerous complexes with 5,5'-dmbipy have been prepared, such as that of zinc (Khalighi et al., 2008), indium (Kalateh et al., 2010), iron (Amani et al., 2007), platin (Amani et al., 2009; Maheshwari et al., 2007), copper (Albada et al., 2004), gold (Karaca et al., 2009), cadmium (Ahmadi et al., 2008,2010) and mercury (Tadayon Pour et al., 2008). Here, we report the synthesis and structure of the title compound.

The asymmetric unit of the title compound, (Fig. 1), contains one half-molecule; a twofold rotation axis passes through the Cd atom. The CdII atom is six-coordinated in a distorted octahedral configuration by two N atoms from 5,5'-dimethyl-2,2'-bipyridine and four bridging Br atoms. The bridging function of the bromide atoms leads to a one-dimensional chain structure. The Cd—Br and Cd—N bond lengths and angles (Table 1) are within normal range [Cd(phen)(µ-Br)2]n, (Zhang, 2007) and [Cd(bipy)(µ-Br)2]n, (Han et al., 2006) [where phen is 1,10-phenanthroline and bipy is 2,2'-bipyridine].

Related literature top

For related structures, see: Ahmadi et al. (2008, 2010); Albada et al. (2004); Amani et al. (2007, 2009); Han et al. (2006); Kalateh et al. (2010); Karaca et al. (2009); Khalighi et al. (2008); Maheshwari et al. (2007); Tadayon Pour et al. (2008); Zhang (2007).

Experimental top

For the preparation of the title compound, a solution of 5,5'-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. The suitable crystals for X-ray diffraction experiment were obtained by methanol diffusion to a colorless solution in DMSO. Suitable crystals were isolated after one week (yield; 0.45 g, 74.1%).

Refinement top

H atoms were positioned geometrically with C—H = 0.93 Å and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level [Symmetry codes: (a) 1 - x,y,1/2 - z].
catena-Poly[[(5,5'-dimethyl-2,2'-bipyridine- κ2N,N')cadmium]-di-µ-bromido] top
Crystal data top
[CdBr2(C12H12N2)]F(000) = 864
Mr = 456.45Dx = 2.209 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 19.637 (5) ÅCell parameters from 5378 reflections
b = 9.6563 (15) Åθ = 2.2–26.0°
c = 7.485 (2) ŵ = 7.39 mm1
β = 104.76 (2)°T = 298 K
V = 1372.4 (6) Å3Prism, colorless
Z = 40.12 × 0.11 × 0.09 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
1346 independent reflections
Radiation source: fine-focus sealed tube1015 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.110
ω scansθmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 2224
Tmin = 0.435, Tmax = 0.548k = 1011
5378 measured reflectionsl = 99
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0403P)2]
where P = (Fo2 + 2Fc2)/3
1346 reflections(Δ/σ)max = 0.004
78 parametersΔρmax = 0.85 e Å3
0 restraintsΔρmin = 0.70 e Å3
Crystal data top
[CdBr2(C12H12N2)]V = 1372.4 (6) Å3
Mr = 456.45Z = 4
Monoclinic, C2/cMo Kα radiation
a = 19.637 (5) ŵ = 7.39 mm1
b = 9.6563 (15) ÅT = 298 K
c = 7.485 (2) Å0.12 × 0.11 × 0.09 mm
β = 104.76 (2)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
1346 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
1015 reflections with I > 2σ(I)
Tmin = 0.435, Tmax = 0.548Rint = 0.110
5378 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.091H-atom parameters constrained
S = 1.03Δρmax = 0.85 e Å3
1346 reflectionsΔρmin = 0.70 e Å3
78 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
xyzUiso*/Ueq
C10.3751 (3)0.2708 (6)0.0036 (8)0.0498 (15)
H10.35650.18430.04350.060*
C20.3367 (3)0.3894 (7)0.0747 (9)0.0549 (16)
C30.2663 (4)0.3740 (9)0.2097 (11)0.085 (3)
H3A0.23550.32210.15370.102*
H3B0.27180.32610.31750.102*
H3C0.24650.46390.24440.102*
C40.3660 (3)0.5147 (7)0.0143 (9)0.0600 (18)
H40.34230.59600.05910.072*
C50.4299 (3)0.5211 (6)0.1118 (8)0.0506 (15)
H50.44940.60670.15270.061*
C60.4659 (3)0.4006 (5)0.1792 (8)0.0421 (13)
N10.4378 (2)0.2774 (5)0.1198 (6)0.0412 (11)
Cd10.50000.07821 (6)0.25000.0476 (2)
Br10.41572 (3)0.09792 (6)0.02140 (9)0.0507 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.041 (3)0.047 (3)0.054 (4)0.004 (3)0.001 (3)0.008 (3)
C20.041 (3)0.066 (4)0.055 (4)0.003 (3)0.008 (3)0.020 (3)
C30.048 (4)0.109 (6)0.086 (6)0.006 (4)0.005 (4)0.034 (5)
C40.055 (4)0.061 (4)0.069 (4)0.026 (3)0.026 (3)0.029 (4)
C50.062 (4)0.040 (3)0.056 (4)0.012 (3)0.027 (3)0.007 (3)
C60.044 (3)0.036 (3)0.049 (3)0.003 (2)0.017 (3)0.007 (2)
N10.033 (2)0.038 (2)0.049 (3)0.0021 (18)0.003 (2)0.006 (2)
Cd10.0456 (4)0.0318 (3)0.0530 (4)0.0000.0102 (3)0.000
Br10.0474 (4)0.0423 (3)0.0550 (4)0.0094 (2)0.0006 (3)0.0064 (2)
Geometric parameters (Å, º) top
C1—N11.339 (6)C5—C61.388 (8)
C1—C21.400 (8)C5—H50.9300
C1—H10.9300C6—N11.339 (7)
C2—C41.366 (10)C6—C6i1.481 (11)
C2—C31.497 (9)Cd1—N12.352 (4)
C3—H3A0.9600Cd1—N1i2.352 (4)
C3—H3B0.9600Cd1—Br12.6676 (8)
C3—H3C0.9600Cd1—Br1i2.6676 (8)
C4—C51.366 (9)Cd1—Br1ii2.9351 (10)
C4—H40.9300Cd1—Br1iii2.9352 (10)
N1—C1—C2122.3 (6)C5—C6—C6i123.0 (4)
N1—C1—H1118.8C6—N1—C1120.0 (5)
C2—C1—H1118.8C6—N1—Cd1117.6 (3)
C4—C2—C1117.3 (5)C1—N1—Cd1122.4 (4)
C4—C2—C3123.3 (6)N1—Cd1—N1i70.3 (2)
C1—C2—C3119.4 (6)N1—Cd1—Br194.81 (10)
C2—C3—H3A109.5N1i—Cd1—Br1163.48 (11)
C2—C3—H3B109.5N1—Cd1—Br1i163.48 (11)
H3A—C3—H3B109.5N1i—Cd1—Br1i94.81 (10)
C2—C3—H3C109.5Br1—Cd1—Br1i100.78 (4)
H3A—C3—H3C109.5N1—Cd1—Br1ii84.78 (12)
H3B—C3—H3C109.5N1i—Cd1—Br1ii89.13 (12)
C5—C4—C2120.2 (6)Br1—Cd1—Br1ii96.79 (3)
C5—C4—H4119.9Br1i—Cd1—Br1ii87.96 (3)
C2—C4—H4119.9N1—Cd1—Br1iii89.13 (12)
C4—C5—C6120.4 (6)N1i—Cd1—Br1iii84.78 (12)
C4—C5—H5119.8Br1—Cd1—Br1iii87.96 (2)
C6—C5—H5119.8Br1i—Cd1—Br1iii96.79 (3)
N1—C6—C5119.7 (5)Br1ii—Cd1—Br1iii172.56 (3)
N1—C6—C6i117.3 (3)Cd1—Br1—Cd1iii92.04 (3)
N1—C1—C2—C40.5 (10)C1—N1—Cd1—N1i177.4 (6)
N1—C1—C2—C3178.9 (6)C6—N1—Cd1—Br1172.9 (4)
C1—C2—C4—C50.6 (10)C1—N1—Cd1—Br110.0 (5)
C3—C2—C4—C5178.8 (6)C6—N1—Cd1—Br1i26.4 (8)
C2—C4—C5—C60.2 (10)C1—N1—Cd1—Br1i150.8 (4)
C4—C5—C6—N10.2 (10)C6—N1—Cd1—Br1ii90.7 (4)
C4—C5—C6—C6i177.8 (7)C1—N1—Cd1—Br1ii86.4 (4)
C5—C6—N1—C10.3 (9)C6—N1—Cd1—Br1iii85.0 (4)
C6i—C6—N1—C1177.8 (6)C1—N1—Cd1—Br1iii97.8 (4)
C5—C6—N1—Cd1177.5 (4)N1—Cd1—Br1—Cd1iii88.96 (12)
C6i—C6—N1—Cd10.5 (9)N1i—Cd1—Br1—Cd1iii63.9 (4)
C2—C1—N1—C60.1 (9)Br1i—Cd1—Br1—Cd1iii96.53 (2)
C2—C1—N1—Cd1177.0 (5)Br1ii—Cd1—Br1—Cd1iii174.26 (2)
C6—N1—Cd1—N1i0.2 (3)Br1iii—Cd1—Br1—Cd1iii0.0
Symmetry codes: (i) x+1, y, z+1/2; (ii) x, y, z+1/2; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formula[CdBr2(C12H12N2)]
Mr456.45
Crystal system, space groupMonoclinic, C2/c
Temperature (K)298
a, b, c (Å)19.637 (5), 9.6563 (15), 7.485 (2)
β (°) 104.76 (2)
V3)1372.4 (6)
Z4
Radiation typeMo Kα
µ (mm1)7.39
Crystal size (mm)0.12 × 0.11 × 0.09
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.435, 0.548
No. of measured, independent and
observed [I > 2σ(I)] reflections
5378, 1346, 1015
Rint0.110
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.091, 1.03
No. of reflections1346
No. of parameters78
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.85, 0.70

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
Cd1—N12.352 (4)Cd1—Br1i2.9351 (10)
Cd1—Br12.6676 (8)
Symmetry code: (i) x, y, z+1/2.
 

Acknowledgements

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

References

First citationAhmadi, R., Kalateh, K. & Amani, V. (2010). Acta Cryst. E66, m562.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationAhmadi, R., Khalighi, A., Kalateh, K., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1233.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationAlbada, G. A., Mohamadou, A., Mutikainen, I., Turpeinen, U. & Reedijk, J. (2004). Eur. J. Inorg. Chem. pp. 3733–3742.  Google Scholar
First citationAmani, V., Safari, N. & Khavasi, H. R. (2007). Polyhedron, 26, 4257–4262.  Web of Science CSD CrossRef CAS Google Scholar
First citationAmani, V., Safari, N., Khavasi, H. R. & Akkurt, M. (2009). Polyhedron, 28, 3026–3030.  Web of Science CSD CrossRef CAS Google Scholar
First citationBruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationHan, J., Fang, J., Dong, Y. & Chang, H. (2006). Acta Cryst. E62, m183–m184.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationKalateh, K., Ahmadi, R. & Amani, V. (2010). Acta Cryst. E66, m512.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationKaraca, S., Akkurt, M., Safari, N., Amani, V., Büyükgüngör, O. & Abedi, A. (2009). Acta Cryst. E65, m335–m336.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationKhalighi, A., Ahmadi, R., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1211–m1212.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationMaheshwari, V., Carlone, M., Fronczek, F. R. & Marzilli, L. G. (2007). Acta Cryst. B63, 603–611.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTadayon Pour, N., Ebadi, A., Abedi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1305.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationZhang, B.-S. (2007). Acta Cryst. E63, m1562.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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