Skip to main content
NCBI home page
Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2010 Sep 11;66(Pt 10):m1236. doi: 10.1107/S1600536810035531

Dichlorido(2,9-dimethyl-1,10-phenanthroline-κ2 N,N′)cobalt(II)

Niloufar Akbarzadeh Torbati a, Ali Reza Rezvani a,*, Nasser Safari b, Vahid Amani b, Hamid Reza Khavasi b
PMCID: PMC2983147  PMID: 21587388

Abstract

In the title compound, [CoCl2(C14H12N2)], the CoII atom is four-coordinated in a distorted tetra­hedral geometry by two N atoms from a 2,9-dimethyl-1,10-phenanthroline ligand and two Cl atoms. The Co atom and the phenanthroline unit are located on a mirror plane. The methyl H atoms are disordered about the mirror plane and areeach half-occupied. In the crystal structure, π–π inter­actions between the pyridine and benzene rings and between the pyridine rings [centroid–centroid distances = 3.8821 (9) and 3.9502 (10) Å, respectively] stabilize the structure.

Related literature

For related structures, see: Alizadeh et al. (2009 ▶); Buttery et al. (2006 ▶); Ding et al. (2006 ▶); Fanizzi et al. (1991 ▶); Lemoine et al. (2003 ▶); Preston & Kennard (1969 ▶); Robinson & Sinn (1975 ▶).graphic file with name e-66-m1236-scheme1.jpg

Experimental

Crystal data

  • [CoCl2(C14H12N2)]

  • M r = 338.09

  • Orthorhombic, Inline graphic

  • a = 11.2434 (12) Å

  • b = 7.441 (1) Å

  • c = 17.690 (3) Å

  • V = 1480.0 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.51 mm−1

  • T = 298 K

  • 0.50 × 0.22 × 0.20 mm

Data collection

  • Stoe IPDS-2 diffractometer

  • Absorption correction: numerical (X-SHAPE and X-RED; Stoe & Cie, 2002 ▶) T min = 0.681, T max = 0.749

  • 9742 measured reflections

  • 2124 independent reflections

  • 1871 reflections with I > 2σ(I)

  • R int = 0.067

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044

  • wR(F 2) = 0.139

  • S = 1.20

  • 2124 reflections

  • 114 parameters

  • H-atom parameters constrained

  • Δρmax = 0.51 e Å−3

  • Δρmin = −0.55 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810035531/hy2350sup1.cif

e-66-m1236-sup1.cif (17.8KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035531/hy2350Isup2.hkl

e-66-m1236-Isup2.hkl (102.4KB, hkl)

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

Table 1. Selected bond lengths (Å).

N1—Co1 2.046 (3)
N2—Co1 2.046 (3)
Cl1—Co1 2.2030 (9)
Open in a new tab

Acknowledgments

We are grateful to the University of Sistan and Baluchestan, and Shahid Beheshti University for financial support.

supplementary crystallographic information

Comment

2,9-Dimethyl-1,10-phenanthroline (dmphen) is a good bidentate ligand, and numerous complexes with dmphen have been prepared, such as those of mercury (Alizadeh et al., 2009), zinc (Preston & Kennard, 1969), copper (Lemoine et al., 2003), nickel (Ding et al., 2006), gold (Robinson & Sinn, 1975), platinum (Fanizzi et al., 1991) and lithium (Buttery et al., 2006). Here, we report the synthesis and structure of the title compound.

In the title compound (Fig. 1), the CoII atom is four-coordinated in a distorted tetrahedral configuration by two N atoms from one dmphen ligand and two Cl atoms (Table 1). In the crystal structure, π–π interactions (Fig. 2) between the pyridyl and benzene rings, Cg3···Cg4i and Cg3···Cg3ii [symmetry codes: (i) -x, 1-y, 2-z; (ii) -x, -1/2+y, 2-z; where Cg3 and Cg4 are the centroids of the N2, C8–C11, C13 ring and C5–C8, C13–C14 ring], with centroid–centroid distances of 3.8821 (9) and 3.9502 (10) Å, stabilize the structure.

Experimental

For the preparation of the title compound, a solution of dmphen (0.42 g, 2.00 mmol) in methanol (20 ml) was added to a solution of CoCl2.6H2O (0.48 g, 2.00 mmol) in methanol (20 ml) at room temperature. Crystals suitable for X-ray diffraction analysis were obtained by methanol diffusion into a blue solution of the title compound in DMSO after one week (yield: 0.50 g, 73.9%; m.p. > 573 K).

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.

Fig. 1.

Open in a new tab

The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (i) x, 3/2-y, z.]

Fig. 2.

Fig. 2.

Open in a new tab

Crystal packing diagram for the title compound.

Crystal data

[CoCl2(C14H12N2)] F(000) = 684
Mr = 338.09 Dx = 1.517 Mg m−3
Orthorhombic, Pnma Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n Cell parameters from 1670 reflections
a = 11.2434 (12) Å θ = 2.2–29.3°
b = 7.441 (1) Å µ = 1.51 mm−1
c = 17.690 (3) Å T = 298 K
V = 1480.0 (4) Å3 Block, blue
Z = 4 0.50 × 0.22 × 0.20 mm
Open in a new tab

Data collection

Stoe IPDS-2 diffractometer 2124 independent reflections
Radiation source: fine-focus sealed tube 1871 reflections with I > 2σ(I)
graphite Rint = 0.067
rotation method scans θmax = 29.3°, θmin = 2.2°
Absorption correction: numerical (X-SHAPE and X-RED; Stoe & Cie, 2002) h = −14→15
Tmin = 0.681, Tmax = 0.749 k = −10→10
9742 measured reflections l = −15→24
Open in a new tab

Refinement

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)] = 0.044 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139 H-atom parameters constrained
S = 1.20 w = 1/[σ2(Fo2) + (0.0692P)2 + 0.4334P] where P = (Fo2 + 2Fc2)/3
2124 reflections (Δ/σ)max = 0.001
114 parameters Δρmax = 0.51 e Å−3
0 restraints Δρmin = −0.55 e Å−3
Open in a new tab

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

x y z Uiso*/Ueq Occ. (<1)
C1 0.5096 (3) 0.7500 0.9952 (3) 0.0677 (12)
H1A 0.4953 0.6880 0.9484 0.102* 0.50
H1B 0.5719 0.6904 1.0224 0.102* 0.50
H1C 0.5329 0.8716 0.9849 0.102* 0.50
C2 0.3980 (3) 0.7500 1.0417 (2) 0.0502 (8)
C3 0.4022 (4) 0.7500 1.1208 (3) 0.0670 (12)
H3 0.4754 0.7500 1.1454 0.080*
C4 0.3002 (4) 0.7500 1.1619 (2) 0.0661 (11)
H4 0.3038 0.7500 1.2145 0.079*
C5 0.1893 (3) 0.7500 1.1254 (2) 0.0470 (7)
C6 0.0776 (4) 0.7500 1.1635 (2) 0.0599 (10)
H6 0.0763 0.7500 1.2161 0.072*
C7 −0.0259 (4) 0.7500 1.1254 (3) 0.0602 (10)
H7 −0.0974 0.7500 1.1518 0.072*
C8 −0.0270 (3) 0.7500 1.0444 (2) 0.0486 (8)
C9 −0.1318 (3) 0.7500 1.0008 (3) 0.0648 (11)
H9 −0.2057 0.7500 1.0244 0.078*
C10 −0.1246 (4) 0.7500 0.9245 (3) 0.0687 (12)
H10 −0.1939 0.7500 0.8959 0.082*
C11 −0.0128 (4) 0.7500 0.8877 (2) 0.0556 (9)
C12 −0.0018 (5) 0.7500 0.8039 (3) 0.0775 (14)
H12A −0.0718 0.8026 0.7821 0.116* 0.50
H12B 0.0067 0.6287 0.7861 0.116* 0.50
H12C 0.0668 0.8187 0.7894 0.116* 0.50
C13 0.0806 (3) 0.7500 1.00504 (19) 0.0393 (6)
C14 0.1911 (3) 0.7500 1.04563 (19) 0.0387 (6)
N1 0.2938 (2) 0.7500 1.00521 (16) 0.0392 (5)
N2 0.0873 (2) 0.7500 0.92773 (17) 0.0423 (6)
Cl1 0.31373 (7) 0.49607 (9) 0.83732 (5) 0.0645 (2)
Co1 0.26015 (4) 0.7500 0.89154 (3) 0.04234 (18)
Open in a new tab

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
C1 0.0351 (16) 0.082 (3) 0.086 (3) 0.000 0.0071 (19) 0.000
C2 0.0353 (14) 0.058 (2) 0.058 (2) 0.000 −0.0052 (14) 0.000
C3 0.050 (2) 0.093 (3) 0.058 (2) 0.000 −0.0196 (18) 0.000
C4 0.062 (2) 0.093 (3) 0.043 (2) 0.000 −0.0126 (18) 0.000
C5 0.0494 (18) 0.0531 (18) 0.0387 (16) 0.000 0.0011 (13) 0.000
C6 0.064 (2) 0.073 (2) 0.0425 (19) 0.000 0.0116 (17) 0.000
C7 0.0507 (19) 0.070 (2) 0.060 (2) 0.000 0.0188 (17) 0.000
C8 0.0363 (15) 0.0488 (17) 0.061 (2) 0.000 0.0026 (14) 0.000
C9 0.0357 (16) 0.070 (3) 0.088 (3) 0.000 −0.0046 (18) 0.000
C10 0.0415 (18) 0.075 (3) 0.089 (3) 0.000 −0.024 (2) 0.000
C11 0.056 (2) 0.0505 (19) 0.061 (2) 0.000 −0.0229 (17) 0.000
C12 0.096 (4) 0.087 (3) 0.049 (2) 0.000 −0.033 (2) 0.000
C13 0.0353 (13) 0.0386 (13) 0.0441 (16) 0.000 −0.0016 (12) 0.000
C14 0.0353 (13) 0.0421 (14) 0.0388 (14) 0.000 −0.0013 (11) 0.000
N1 0.0331 (11) 0.0438 (13) 0.0409 (14) 0.000 −0.0001 (10) 0.000
N2 0.0413 (13) 0.0436 (13) 0.0420 (14) 0.000 −0.0063 (11) 0.000
Cl1 0.0738 (5) 0.0488 (4) 0.0707 (5) 0.0020 (3) 0.0176 (4) −0.0121 (3)
Co1 0.0470 (3) 0.0423 (3) 0.0378 (3) 0.000 0.00572 (17) 0.000
Open in a new tab

Geometric parameters (Å, °)

C1—C2 1.500 (5) C8—C9 1.408 (5)
C1—H1A 0.9600 C9—C10 1.352 (8)
C1—H1B 0.9600 C9—H9 0.9300
C1—H1C 0.9600 C10—C11 1.416 (7)
C2—N1 1.337 (4) C10—H10 0.9300
C2—C3 1.401 (6) C11—N2 1.330 (4)
C3—C4 1.358 (7) C11—C12 1.487 (6)
C3—H3 0.9300 C12—H12A 0.9600
C4—C5 1.405 (6) C12—H12B 0.9600
C4—H4 0.9300 C12—H12C 0.9600
C5—C14 1.411 (5) C13—N2 1.370 (4)
C5—C6 1.426 (5) C13—C14 1.434 (4)
C6—C7 1.345 (6) C14—N1 1.359 (4)
C6—H6 0.9300 N1—Co1 2.046 (3)
C7—C8 1.433 (6) N2—Co1 2.046 (3)
C7—H7 0.9300 Cl1—Co1 2.2030 (9)
C8—C13 1.396 (5) Co1—Cl1i 2.2030 (9)
C2—C1—H1A 109.5 C9—C10—C11 120.9 (4)
C2—C1—H1B 109.5 C9—C10—H10 119.6
H1A—C1—H1B 109.5 C11—C10—H10 119.6
C2—C1—H1C 109.5 N2—C11—C10 120.4 (4)
H1A—C1—H1C 109.5 N2—C11—C12 117.4 (4)
H1B—C1—H1C 109.5 C10—C11—C12 122.2 (4)
N1—C2—C3 120.8 (4) C11—C12—H12A 109.5
N1—C2—C1 117.9 (4) C11—C12—H12B 109.5
C3—C2—C1 121.4 (4) H12A—C12—H12B 109.5
C4—C3—C2 120.4 (4) C11—C12—H12C 109.5
C4—C3—H3 119.8 H12A—C12—H12C 109.5
C2—C3—H3 119.8 H12B—C12—H12C 109.5
C3—C4—C5 120.2 (4) N2—C13—C8 123.0 (3)
C3—C4—H4 119.9 N2—C13—C14 116.9 (3)
C5—C4—H4 119.9 C8—C13—C14 120.1 (3)
C4—C5—C14 116.6 (3) N1—C14—C5 122.6 (3)
C4—C5—C6 124.3 (4) N1—C14—C13 118.2 (3)
C14—C5—C6 119.1 (3) C5—C14—C13 119.2 (3)
C7—C6—C5 121.6 (4) C2—N1—C14 119.4 (3)
C7—C6—H6 119.2 C2—N1—Co1 129.5 (2)
C5—C6—H6 119.2 C14—N1—Co1 111.1 (2)
C6—C7—C8 120.6 (3) C11—N2—C13 119.1 (3)
C6—C7—H7 119.7 C11—N2—Co1 129.6 (3)
C8—C7—H7 119.7 C13—N2—Co1 111.3 (2)
C13—C8—C9 116.9 (4) N1—Co1—N2 82.44 (11)
C13—C8—C7 119.4 (3) N1—Co1—Cl1 112.17 (4)
C9—C8—C7 123.7 (4) N2—Co1—Cl1 113.31 (4)
C10—C9—C8 119.7 (4) N1—Co1—Cl1i 112.17 (4)
C10—C9—H9 120.1 N2—Co1—Cl1i 113.34 (4)
C8—C9—H9 120.1 Cl1—Co1—Cl1i 118.12 (5)
N1—C2—C3—C4 0.000 (3) C1—C2—N1—C14 180.000 (1)
C1—C2—C3—C4 180.000 (2) C3—C2—N1—Co1 180.000 (1)
C2—C3—C4—C5 0.000 (3) C1—C2—N1—Co1 0.000 (2)
C3—C4—C5—C14 0.000 (2) C5—C14—N1—C2 0.000 (2)
C3—C4—C5—C6 180.000 (2) C13—C14—N1—C2 180.000 (1)
C4—C5—C6—C7 180.000 (2) C5—C14—N1—Co1 180.000 (1)
C14—C5—C6—C7 0.000 (3) C13—C14—N1—Co1 0.000 (1)
C5—C6—C7—C8 0.000 (3) C10—C11—N2—C13 0.000 (2)
C6—C7—C8—C13 0.000 (2) C12—C11—N2—C13 180.000 (2)
C6—C7—C8—C9 180.000 (2) C10—C11—N2—Co1 180.000 (1)
C13—C8—C9—C10 0.000 (2) C12—C11—N2—Co1 0.000 (1)
C7—C8—C9—C10 180.000 (2) C8—C13—N2—C11 0.000 (2)
C8—C9—C10—C11 0.000 (2) C14—C13—N2—C11 180.000 (1)
C9—C10—C11—N2 0.000 (2) C8—C13—N2—Co1 180.000 (1)
C9—C10—C11—C12 180.000 (2) C14—C13—N2—Co1 0.000 (1)
C9—C8—C13—N2 0.000 (2) C2—N1—Co1—N2 180.000 (1)
C7—C8—C13—N2 180.000 (2) C14—N1—Co1—N2 0.000 (1)
C9—C8—C13—C14 180.000 (1) C2—N1—Co1—Cl1 67.86 (4)
C7—C8—C13—C14 0.000 (2) C14—N1—Co1—Cl1 −112.14 (4)
C4—C5—C14—N1 0.000 (2) C2—N1—Co1—Cl1i −67.82 (4)
C6—C5—C14—N1 180.000 (2) C14—N1—Co1—Cl1i 112.18 (4)
C4—C5—C14—C13 180.000 (2) C11—N2—Co1—N1 180.000 (1)
C6—C5—C14—C13 0.000 (2) C13—N2—Co1—N1 0.000 (1)
N2—C13—C14—N1 0.000 (2) C11—N2—Co1—Cl1 −69.07 (5)
C8—C13—C14—N1 180.000 (1) C13—N2—Co1—Cl1 110.93 (5)
N2—C13—C14—C5 180.000 (2) C11—N2—Co1—Cl1i 69.07 (5)
C8—C13—C14—C5 0.000 (2) C13—N2—Co1—Cl1i −110.93 (5)
C3—C2—N1—C14 0.000 (2)
Open in a new tab

Symmetry codes: (i) x, −y+3/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2350).

References

  1. Alizadeh, R., Heidari, A., Ahmadi, R. & Amani, V. (2009). Acta Cryst. E65, m483–m484. [DOI] [PMC free article] [PubMed]
  2. Buttery, J. H. N., Effendy, Mutrofin, S., Plackett, N. C., Skelton, B. W., Whitaker, C. R. & White, A. H. (2006). Z. Anorg. Allg. Chem.632, 1809–1828.
  3. Ding, C.-F., Miao, Y.-F., Tian, B.-Q., Li, X.-M. & Zhang, S.-S. (2006). Acta Cryst. E62, m1062–m1063.
  4. Fanizzi, F. P., Intini, F. P., Maresca, L., Natile, G., Lanfranchi, M. & Tiripicchio, A. (1991). J. Chem. Soc. Dalton Trans. pp. 1007–1015.
  5. Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  6. Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  7. Lemoine, P., Viossat, B. & Daran, J.-C. (2003). Acta Cryst. E59, m17–m19.
  8. Preston, H. S. & Kennard, C. H. L. (1969). J. Chem. Soc. A, pp. 1956–1961.
  9. Robinson, W. T. & Sinn, E. (1975). J. Chem. Soc. Dalton Trans. pp. 726–731.
  10. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  11. Stoe & Cie (2002). X-AREA, X-RED and X-SHAPE Stoe & Cie, Darmstadt, Germany.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810035531/hy2350sup1.cif

e-66-m1236-sup1.cif (17.8KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035531/hy2350Isup2.hkl

e-66-m1236-Isup2.hkl (102.4KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

RESOURCES