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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810035531/hy2350sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536810035531/hy2350Isup2.hkl
Contains datablock I

CCDC reference: 768622

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.044
  • wR factor = 0.139
  • Data-to-parameter ratio = 18.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 28 PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 8 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 23
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

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, ππ 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.

Related literature top

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).

Experimental top

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 top

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).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (i) x, 3/2-y, z.]
[Figure 2] Fig. 2. Crystal packing diagram for the title compound.
Dichlorido(2,9-dimethyl-1,10-phenanthroline-κ2N,N')cobalt(II) top
Crystal data top
[CoCl2(C14H12N2)]F(000) = 684
Mr = 338.09Dx = 1.517 Mg m3
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 1670 reflections
a = 11.2434 (12) Åθ = 2.2–29.3°
b = 7.441 (1) ŵ = 1.51 mm1
c = 17.690 (3) ÅT = 298 K
V = 1480.0 (4) Å3Block, blue
Z = 40.50 × 0.22 × 0.20 mm
Data collection top
Stoe IPDS-2
diffractometer
2124 independent reflections
Radiation source: fine-focus sealed tube1871 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.067
rotation method scansθmax = 29.3°, θmin = 2.2°
Absorption correction: numerical
(X-SHAPE and X-RED; Stoe & Cie, 2002)
h = 1415
Tmin = 0.681, Tmax = 0.749k = 1010
9742 measured reflectionsl = 1524
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H-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 parametersΔρmax = 0.51 e Å3
0 restraintsΔρmin = 0.55 e Å3
Crystal data top
[CoCl2(C14H12N2)]V = 1480.0 (4) Å3
Mr = 338.09Z = 4
Orthorhombic, PnmaMo Kα radiation
a = 11.2434 (12) ŵ = 1.51 mm1
b = 7.441 (1) ÅT = 298 K
c = 17.690 (3) Å0.50 × 0.22 × 0.20 mm
Data collection top
Stoe IPDS-2
diffractometer
2124 independent reflections
Absorption correction: numerical
(X-SHAPE and X-RED; Stoe & Cie, 2002)
1871 reflections with I > 2σ(I)
Tmin = 0.681, Tmax = 0.749Rint = 0.067
9742 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.139H-atom parameters constrained
S = 1.20Δρmax = 0.51 e Å3
2124 reflectionsΔρmin = 0.55 e Å3
114 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.5096 (3)0.75000.9952 (3)0.0677 (12)
H1A0.49530.68800.94840.102*0.50
H1B0.57190.69041.02240.102*0.50
H1C0.53290.87160.98490.102*0.50
C20.3980 (3)0.75001.0417 (2)0.0502 (8)
C30.4022 (4)0.75001.1208 (3)0.0670 (12)
H30.47540.75001.14540.080*
C40.3002 (4)0.75001.1619 (2)0.0661 (11)
H40.30380.75001.21450.079*
C50.1893 (3)0.75001.1254 (2)0.0470 (7)
C60.0776 (4)0.75001.1635 (2)0.0599 (10)
H60.07630.75001.21610.072*
C70.0259 (4)0.75001.1254 (3)0.0602 (10)
H70.09740.75001.15180.072*
C80.0270 (3)0.75001.0444 (2)0.0486 (8)
C90.1318 (3)0.75001.0008 (3)0.0648 (11)
H90.20570.75001.02440.078*
C100.1246 (4)0.75000.9245 (3)0.0687 (12)
H100.19390.75000.89590.082*
C110.0128 (4)0.75000.8877 (2)0.0556 (9)
C120.0018 (5)0.75000.8039 (3)0.0775 (14)
H12A0.07180.80260.78210.116*0.50
H12B0.00670.62870.78610.116*0.50
H12C0.06680.81870.78940.116*0.50
C130.0806 (3)0.75001.00504 (19)0.0393 (6)
C140.1911 (3)0.75001.04563 (19)0.0387 (6)
N10.2938 (2)0.75001.00521 (16)0.0392 (5)
N20.0873 (2)0.75000.92773 (17)0.0423 (6)
Cl10.31373 (7)0.49607 (9)0.83732 (5)0.0645 (2)
Co10.26015 (4)0.75000.89154 (3)0.04234 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0351 (16)0.082 (3)0.086 (3)0.0000.0071 (19)0.000
C20.0353 (14)0.058 (2)0.058 (2)0.0000.0052 (14)0.000
C30.050 (2)0.093 (3)0.058 (2)0.0000.0196 (18)0.000
C40.062 (2)0.093 (3)0.043 (2)0.0000.0126 (18)0.000
C50.0494 (18)0.0531 (18)0.0387 (16)0.0000.0011 (13)0.000
C60.064 (2)0.073 (2)0.0425 (19)0.0000.0116 (17)0.000
C70.0507 (19)0.070 (2)0.060 (2)0.0000.0188 (17)0.000
C80.0363 (15)0.0488 (17)0.061 (2)0.0000.0026 (14)0.000
C90.0357 (16)0.070 (3)0.088 (3)0.0000.0046 (18)0.000
C100.0415 (18)0.075 (3)0.089 (3)0.0000.024 (2)0.000
C110.056 (2)0.0505 (19)0.061 (2)0.0000.0229 (17)0.000
C120.096 (4)0.087 (3)0.049 (2)0.0000.033 (2)0.000
C130.0353 (13)0.0386 (13)0.0441 (16)0.0000.0016 (12)0.000
C140.0353 (13)0.0421 (14)0.0388 (14)0.0000.0013 (11)0.000
N10.0331 (11)0.0438 (13)0.0409 (14)0.0000.0001 (10)0.000
N20.0413 (13)0.0436 (13)0.0420 (14)0.0000.0063 (11)0.000
Cl10.0738 (5)0.0488 (4)0.0707 (5)0.0020 (3)0.0176 (4)0.0121 (3)
Co10.0470 (3)0.0423 (3)0.0378 (3)0.0000.00572 (17)0.000
Geometric parameters (Å, º) top
C1—C21.500 (5)C8—C91.408 (5)
C1—H1A0.9600C9—C101.352 (8)
C1—H1B0.9600C9—H90.9300
C1—H1C0.9600C10—C111.416 (7)
C2—N11.337 (4)C10—H100.9300
C2—C31.401 (6)C11—N21.330 (4)
C3—C41.358 (7)C11—C121.487 (6)
C3—H30.9300C12—H12A0.9600
C4—C51.405 (6)C12—H12B0.9600
C4—H40.9300C12—H12C0.9600
C5—C141.411 (5)C13—N21.370 (4)
C5—C61.426 (5)C13—C141.434 (4)
C6—C71.345 (6)C14—N11.359 (4)
C6—H60.9300N1—Co12.046 (3)
C7—C81.433 (6)N2—Co12.046 (3)
C7—H70.9300Cl1—Co12.2030 (9)
C8—C131.396 (5)Co1—Cl1i2.2030 (9)
C2—C1—H1A109.5C9—C10—C11120.9 (4)
C2—C1—H1B109.5C9—C10—H10119.6
H1A—C1—H1B109.5C11—C10—H10119.6
C2—C1—H1C109.5N2—C11—C10120.4 (4)
H1A—C1—H1C109.5N2—C11—C12117.4 (4)
H1B—C1—H1C109.5C10—C11—C12122.2 (4)
N1—C2—C3120.8 (4)C11—C12—H12A109.5
N1—C2—C1117.9 (4)C11—C12—H12B109.5
C3—C2—C1121.4 (4)H12A—C12—H12B109.5
C4—C3—C2120.4 (4)C11—C12—H12C109.5
C4—C3—H3119.8H12A—C12—H12C109.5
C2—C3—H3119.8H12B—C12—H12C109.5
C3—C4—C5120.2 (4)N2—C13—C8123.0 (3)
C3—C4—H4119.9N2—C13—C14116.9 (3)
C5—C4—H4119.9C8—C13—C14120.1 (3)
C4—C5—C14116.6 (3)N1—C14—C5122.6 (3)
C4—C5—C6124.3 (4)N1—C14—C13118.2 (3)
C14—C5—C6119.1 (3)C5—C14—C13119.2 (3)
C7—C6—C5121.6 (4)C2—N1—C14119.4 (3)
C7—C6—H6119.2C2—N1—Co1129.5 (2)
C5—C6—H6119.2C14—N1—Co1111.1 (2)
C6—C7—C8120.6 (3)C11—N2—C13119.1 (3)
C6—C7—H7119.7C11—N2—Co1129.6 (3)
C8—C7—H7119.7C13—N2—Co1111.3 (2)
C13—C8—C9116.9 (4)N1—Co1—N282.44 (11)
C13—C8—C7119.4 (3)N1—Co1—Cl1112.17 (4)
C9—C8—C7123.7 (4)N2—Co1—Cl1113.31 (4)
C10—C9—C8119.7 (4)N1—Co1—Cl1i112.17 (4)
C10—C9—H9120.1N2—Co1—Cl1i113.34 (4)
C8—C9—H9120.1Cl1—Co1—Cl1i118.12 (5)
N1—C2—C3—C40.000 (3)C1—C2—N1—C14180.000 (1)
C1—C2—C3—C4180.000 (2)C3—C2—N1—Co1180.000 (1)
C2—C3—C4—C50.000 (3)C1—C2—N1—Co10.000 (2)
C3—C4—C5—C140.000 (2)C5—C14—N1—C20.000 (2)
C3—C4—C5—C6180.000 (2)C13—C14—N1—C2180.000 (1)
C4—C5—C6—C7180.000 (2)C5—C14—N1—Co1180.000 (1)
C14—C5—C6—C70.000 (3)C13—C14—N1—Co10.000 (1)
C5—C6—C7—C80.000 (3)C10—C11—N2—C130.000 (2)
C6—C7—C8—C130.000 (2)C12—C11—N2—C13180.000 (2)
C6—C7—C8—C9180.000 (2)C10—C11—N2—Co1180.000 (1)
C13—C8—C9—C100.000 (2)C12—C11—N2—Co10.000 (1)
C7—C8—C9—C10180.000 (2)C8—C13—N2—C110.000 (2)
C8—C9—C10—C110.000 (2)C14—C13—N2—C11180.000 (1)
C9—C10—C11—N20.000 (2)C8—C13—N2—Co1180.000 (1)
C9—C10—C11—C12180.000 (2)C14—C13—N2—Co10.000 (1)
C9—C8—C13—N20.000 (2)C2—N1—Co1—N2180.000 (1)
C7—C8—C13—N2180.000 (2)C14—N1—Co1—N20.000 (1)
C9—C8—C13—C14180.000 (1)C2—N1—Co1—Cl167.86 (4)
C7—C8—C13—C140.000 (2)C14—N1—Co1—Cl1112.14 (4)
C4—C5—C14—N10.000 (2)C2—N1—Co1—Cl1i67.82 (4)
C6—C5—C14—N1180.000 (2)C14—N1—Co1—Cl1i112.18 (4)
C4—C5—C14—C13180.000 (2)C11—N2—Co1—N1180.000 (1)
C6—C5—C14—C130.000 (2)C13—N2—Co1—N10.000 (1)
N2—C13—C14—N10.000 (2)C11—N2—Co1—Cl169.07 (5)
C8—C13—C14—N1180.000 (1)C13—N2—Co1—Cl1110.93 (5)
N2—C13—C14—C5180.000 (2)C11—N2—Co1—Cl1i69.07 (5)
C8—C13—C14—C50.000 (2)C13—N2—Co1—Cl1i110.93 (5)
C3—C2—N1—C140.000 (2)
Symmetry code: (i) x, y+3/2, z.

Experimental details

Crystal data
Chemical formula[CoCl2(C14H12N2)]
Mr338.09
Crystal system, space groupOrthorhombic, Pnma
Temperature (K)298
a, b, c (Å)11.2434 (12), 7.441 (1), 17.690 (3)
V3)1480.0 (4)
Z4
Radiation typeMo Kα
µ (mm1)1.51
Crystal size (mm)0.50 × 0.22 × 0.20
Data collection
DiffractometerStoe IPDS2
diffractometer
Absorption correctionNumerical
(X-SHAPE and X-RED; Stoe & Cie, 2002)
Tmin, Tmax0.681, 0.749
No. of measured, independent and
observed [I > 2σ(I)] reflections
9742, 2124, 1871
Rint0.067
(sin θ/λ)max1)0.688
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.139, 1.20
No. of reflections2124
No. of parameters114
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.51, 0.55

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top
N1—Co12.046 (3)Cl1—Co12.2030 (9)
N2—Co12.046 (3)
 

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