Dichlorido(2,9-dimethyl-1,10-phenanthroline-κN,N')cobalt(II).

In the title compound, [CoCl(2)(C(14)H(12)N(2))], the Co(II) atom is four-coordinated in a distorted tetra-hedral 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 inter-actions 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 ▶).

Experimental

Crystal data

[CoCl2(C14H12N2)]

M = 338.09

Orthorhombic,

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 ▶).

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

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

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

[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

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

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

	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)

	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

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)

Table 1

Selected bond lengths (Å)

N1—Co1	2.046 (3)
N2—Co1	2.046 (3)
Cl1—Co1	2.2030 (9)