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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): m1024.
Published online 2010 July 31. doi:  10.1107/S1600536810029399
PMCID: PMC3007525

Dichlorido(6,6′-dimethyl-2,2′-bipyridine-κ2 N,N′)cadmium(II)

Abstract

In the title compound, [CdCl2(C12H12N2)], the CdII 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 Cl atoms. Inter­molecular C—H(...)Cl hydrogen bonds and π–π stacking inter­actions between the pyridyl rings [centroid–centroid distance = 3.7337 (18) Å] are present in the crystal structure.

Related literature

For related structures, see: Alizadeh, Kalateh, Ebadi et al. (2009 [triangle]); Alizadeh, Kalateh, Khoshtarkib et al. (2009 [triangle]); Alizadeh, Khoshtarkib et al. (2009 [triangle]); Itoh et al. (2005 [triangle]); Kou et al. (2008 [triangle]); Onggo et al. (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1024-scheme1.jpg

Experimental

Crystal data

  • [CdCl2(C12H12N2)]
  • M r = 367.55
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1024-efi1.jpg
  • a = 7.6715 (9) Å
  • b = 10.0970 (16) Å
  • c = 17.902 (2) Å
  • β = 97.474 (9)°
  • V = 1374.9 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.96 mm−1
  • T = 298 K
  • 0.50 × 0.25 × 0.17 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.569, T max = 0.723
  • 9684 measured reflections
  • 3656 independent reflections
  • 3162 reflections with I > 2σ(I)
  • R int = 0.045

Refinement

  • R[F 2 > 2σ(F 2)] = 0.033
  • wR(F 2) = 0.086
  • S = 1.08
  • 3656 reflections
  • 154 parameters
  • H-atom parameters constrained
  • Δρmax = 0.57 e Å−3
  • Δρmin = −0.63 e Å−3

Data collection: SMART (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536810029399/hy2335sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029399/hy2335Isup2.hkl

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

Acknowledgments

We are grateful to Damghan University for financial support.

supplementary crystallographic information

Comment

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 those of zinc (Alizadeh, Kalateh, Ebadi et al., 2009; Alizadeh, Kalateh, Khoshtarkib, et al., 2009; Alizadeh, Khoshtarkib et al., 2009), copper (Itoh et al., 2005), nickel (Kou et al., 2008) and ruthenium (Onggo et al., 2005). 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'-dmbipy ligand and two terminal Cl atoms. The Cd—N and Cd—Cl bond lengths and angles are normal (Table 1). In the crystal structure, intermolecular C—H···Cl hydrogen bonds (Table 2) and π–π contacts (Fig. 2) between the pyridyl rings, Cg1···Cg2i [symmetry code: (i) 1-x, -y, 1-z. Cg1 and Cg2 are centroids of the N1, C2—C6 ring and the N2, C7—C11 ring], stabilize the structure, with a centroid–centroid distance of 3.7337 (18) Å.

Experimental

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 CdCl2.H2O (0.27 g, 1.33 mmol) in methanol (5 ml) at room temperature. Crystals suitable for X-ray diffraction experiment were obtained by methanol diffusion into a colorless solution of the title compound in DMSO after one week (yield: 0.35 g, 71.6%).

Refinement

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 (aromatic) and 0.96 (methyl) Å and with Uiso(H) = 1.2Ueq(C).

Figures

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. Dashed lines denote hydrogen bonds.

Crystal data

[CdCl2(C12H12N2)]F(000) = 720
Mr = 367.55Dx = 1.776 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 899 reflections
a = 7.6715 (9) Åθ = 2.3–29.2°
b = 10.0970 (16) ŵ = 1.96 mm1
c = 17.902 (2) ÅT = 298 K
β = 97.474 (9)°Block, colorless
V = 1374.9 (3) Å30.50 × 0.25 × 0.17 mm
Z = 4

Data collection

Bruker APEX CCD diffractometer3656 independent reflections
Radiation source: fine-focus sealed tube3162 reflections with I > 2σ(I)
graphiteRint = 0.045
[var phi] and ω scansθmax = 29.2°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.569, Tmax = 0.723k = −11→13
9684 measured reflectionsl = −24→24

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.0364P)2 + 0.7364P] where P = (Fo2 + 2Fc2)/3
3656 reflections(Δ/σ)max = 0.001
154 parametersΔρmax = 0.57 e Å3
0 restraintsΔρmin = −0.63 e Å3

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

xyzUiso*/Ueq
C10.3527 (5)0.0531 (4)0.26805 (18)0.0737 (9)
H1A0.43860.12150.28050.088*
H1B0.24000.09270.25260.088*
H1C0.38610.00020.22770.088*
C20.3427 (4)−0.0323 (3)0.33533 (16)0.0526 (6)
C30.3765 (4)−0.1659 (3)0.3346 (2)0.0690 (9)
H30.4058−0.20600.29120.083*
C40.3668 (5)−0.2393 (3)0.3977 (3)0.0754 (11)
H40.3912−0.32960.39780.090*
C50.3202 (4)−0.1785 (3)0.4621 (2)0.0634 (8)
H50.3131−0.22760.50550.076*
C60.2846 (3)−0.0442 (2)0.46048 (15)0.0451 (5)
C70.2319 (3)0.0282 (3)0.52617 (13)0.0435 (5)
C80.2145 (4)−0.0343 (3)0.59409 (17)0.0613 (8)
H80.2401−0.12390.60050.074*
C90.1589 (5)0.0381 (4)0.65159 (17)0.0698 (9)
H90.1458−0.00260.69710.084*
C100.1233 (4)0.1690 (4)0.64177 (16)0.0638 (8)
H100.08520.21830.68040.077*
C110.1442 (4)0.2293 (3)0.57342 (15)0.0512 (6)
C120.1080 (6)0.3718 (3)0.5588 (2)0.0744 (9)
H12A0.01640.38110.51720.089*
H12B0.21270.41460.54690.089*
H12C0.07150.41200.60280.089*
N10.2975 (3)0.0269 (2)0.39745 (11)0.0432 (4)
N20.1971 (3)0.1583 (2)0.51688 (10)0.0416 (4)
Cd10.23178 (3)0.245465 (17)0.402558 (10)0.04588 (8)
Cl10.47640 (12)0.38850 (9)0.39295 (5)0.0758 (2)
Cl2−0.03250 (11)0.31365 (9)0.32689 (4)0.0646 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.098 (3)0.074 (2)0.0528 (16)0.0060 (19)0.0223 (16)−0.0106 (15)
C20.0483 (14)0.0502 (15)0.0586 (15)0.0060 (11)0.0044 (11)−0.0126 (12)
C30.0651 (18)0.0542 (17)0.086 (2)0.0132 (14)0.0011 (16)−0.0255 (17)
C40.068 (2)0.0414 (16)0.112 (3)0.0141 (13)−0.006 (2)−0.0137 (16)
C50.0637 (17)0.0381 (14)0.084 (2)0.0048 (12)−0.0088 (15)0.0090 (13)
C60.0398 (12)0.0360 (11)0.0563 (13)−0.0014 (9)−0.0060 (10)0.0041 (10)
C70.0396 (11)0.0452 (13)0.0438 (12)−0.0055 (9)−0.0017 (9)0.0094 (10)
C80.0597 (16)0.0636 (18)0.0590 (16)−0.0095 (14)0.0019 (13)0.0260 (14)
C90.0691 (19)0.096 (3)0.0444 (14)−0.0182 (18)0.0075 (13)0.0219 (16)
C100.0610 (17)0.092 (3)0.0399 (13)−0.0105 (16)0.0103 (11)−0.0033 (14)
C110.0536 (14)0.0589 (16)0.0417 (12)−0.0037 (12)0.0078 (10)−0.0053 (11)
C120.106 (3)0.0579 (19)0.0631 (18)0.0082 (18)0.0232 (18)−0.0126 (15)
N10.0445 (10)0.0377 (10)0.0469 (10)0.0011 (8)0.0041 (8)−0.0034 (8)
N20.0452 (10)0.0430 (10)0.0363 (9)−0.0023 (8)0.0040 (7)0.0022 (8)
Cd10.05923 (13)0.03760 (12)0.04198 (11)0.00404 (7)0.01099 (8)0.00679 (6)
Cl10.0785 (5)0.0607 (5)0.0887 (6)−0.0146 (4)0.0127 (4)0.0244 (4)
Cl20.0668 (4)0.0701 (5)0.0562 (4)0.0142 (4)0.0048 (3)0.0153 (3)

Geometric parameters (Å, °)

C1—C21.491 (5)C8—C91.374 (5)
C1—H1A0.9600C8—H80.9300
C1—H1B0.9600C9—C101.357 (6)
C1—H1C0.9600C9—H90.9300
C2—N11.347 (3)C10—C111.394 (4)
C2—C31.374 (4)C10—H100.9300
C3—C41.361 (6)C11—N21.346 (3)
C3—H30.9300C11—C121.482 (4)
C4—C51.394 (6)C12—H12A0.9600
C4—H40.9300C12—H12B0.9600
C5—C61.383 (4)C12—H12C0.9600
C5—H50.9300Cd1—N12.268 (2)
C6—N11.352 (3)Cd1—N22.2752 (19)
C6—C71.485 (4)Cd1—Cl12.3919 (9)
C7—N21.345 (3)Cd1—Cl22.3885 (8)
C7—C81.392 (3)
C2—C1—H1A109.5C10—C9—C8119.9 (3)
C2—C1—H1B109.5C10—C9—H9120.1
H1A—C1—H1B109.5C8—C9—H9120.1
C2—C1—H1C109.5C9—C10—C11119.7 (3)
H1A—C1—H1C109.5C9—C10—H10120.2
H1B—C1—H1C109.5C11—C10—H10120.2
N1—C2—C3120.8 (3)N2—C11—C10120.5 (3)
N1—C2—C1117.1 (3)N2—C11—C12116.9 (3)
C3—C2—C1122.0 (3)C10—C11—C12122.6 (3)
C4—C3—C2119.8 (3)C11—C12—H12A109.5
C4—C3—H3120.1C11—C12—H12B109.5
C2—C3—H3120.1H12A—C12—H12B109.5
C3—C4—C5119.6 (3)C11—C12—H12C109.5
C3—C4—H4120.2H12A—C12—H12C109.5
C5—C4—H4120.2H12B—C12—H12C109.5
C6—C5—C4119.1 (3)C2—N1—C6120.6 (2)
C6—C5—H5120.5C2—N1—Cd1123.18 (18)
C4—C5—H5120.5C6—N1—Cd1116.24 (16)
N1—C6—C5120.1 (3)C7—N2—C11120.1 (2)
N1—C6—C7117.2 (2)C7—N2—Cd1116.38 (16)
C5—C6—C7122.7 (3)C11—N2—Cd1123.52 (18)
N2—C7—C8120.7 (3)N1—Cd1—N273.28 (8)
N2—C7—C6116.9 (2)N1—Cd1—Cl2115.75 (6)
C8—C7—C6122.4 (3)N2—Cd1—Cl2115.59 (6)
C9—C8—C7119.2 (3)N1—Cd1—Cl1113.82 (6)
C9—C8—H8120.4N2—Cd1—Cl1118.88 (6)
C7—C8—H8120.4Cl2—Cd1—Cl1113.65 (3)
N1—C2—C3—C4−1.0 (5)C5—C6—N1—Cd1179.2 (2)
C1—C2—C3—C4179.5 (3)C7—C6—N1—Cd1−1.0 (3)
C2—C3—C4—C51.0 (5)C8—C7—N2—C11−0.3 (4)
C3—C4—C5—C60.0 (5)C6—C7—N2—C11178.2 (2)
C4—C5—C6—N1−1.0 (4)C8—C7—N2—Cd1−179.97 (19)
C4—C5—C6—C7179.2 (3)C6—C7—N2—Cd1−1.4 (3)
N1—C6—C7—N21.6 (3)C10—C11—N2—C7−0.5 (4)
C5—C6—C7—N2−178.6 (2)C12—C11—N2—C7−179.8 (3)
N1—C6—C7—C8−179.9 (2)C10—C11—N2—Cd1179.1 (2)
C5—C6—C7—C8−0.1 (4)C12—C11—N2—Cd1−0.2 (4)
N2—C7—C8—C90.9 (4)C2—N1—Cd1—N2178.4 (2)
C6—C7—C8—C9−177.6 (3)C6—N1—Cd1—N20.18 (16)
C7—C8—C9—C10−0.5 (5)C2—N1—Cd1—Cl267.6 (2)
C8—C9—C10—C11−0.3 (5)C6—N1—Cd1—Cl2−110.67 (16)
C9—C10—C11—N20.8 (5)C2—N1—Cd1—Cl1−66.8 (2)
C9—C10—C11—C12−179.9 (3)C6—N1—Cd1—Cl1114.92 (16)
C3—C2—N1—C60.1 (4)C7—N2—Cd1—N10.69 (16)
C1—C2—N1—C6179.5 (3)C11—N2—Cd1—N1−179.0 (2)
C3—C2—N1—Cd1−178.1 (2)C7—N2—Cd1—Cl2111.73 (16)
C1—C2—N1—Cd11.4 (4)C11—N2—Cd1—Cl2−67.9 (2)
C5—C6—N1—C20.9 (4)C7—N2—Cd1—Cl1−107.72 (16)
C7—C6—N1—C2−179.3 (2)C11—N2—Cd1—Cl172.6 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C1—H1C···Cl1i0.962.763.711 (4)169
C5—H5···Cl1ii0.932.793.551 (3)140

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, −y, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2335).

References

  • Alizadeh, R., Kalateh, K., Ebadi, A., Ahmadi, R. & Amani, V. (2009). Acta Cryst. E65, m1250. [PMC free article] [PubMed]
  • Alizadeh, R., Kalateh, K., Khoshtarkib, Z., Ahmadi, R. & Amani, V. (2009). Acta Cryst. E65, m1439–m1440. [PMC free article] [PubMed]
  • Alizadeh, R., Khoshtarkib, Z., Chegeni, K., Ebadi, A. & Amani, V. (2009). Acta Cryst. E65, m1311. [PMC free article] [PubMed]
  • Bruker (2007). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Itoh, S., Kishikawa, N., Suzuki, T. & Takagi, H. D. (2005). Dalton Trans. pp. 1066–1078. [PubMed]
  • Kou, H. Z., Hishiya, S. & Sato, O. (2008). Inorg. Chim. Acta, 361, 2396–2406.
  • Onggo, D., Scudder, M. L., Craig, D. C. & Goodwin, H. A. (2005). J. Mol. Struct.738, 129–136.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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