(Acetato-κ(2)O,O')(acetato-κO)bis(2-amino-3-methyl-pyridine-κN(1))cobalt(II).

In the title compound, [Co(CH(3)COO)(2)(C(6)H(8)N(2))(2)], the Co(II) ion is five-coordinated by two pyridine N atoms from two 2-amino-3-methyl-pyridine ligands, two O atoms from one acetate ion and one O atom from another acetate ion in a distorted trigonal-bipyramidal geometry. The pyridine rings are nearly perpendicular to each other [dihedral angle = 84.49 (16)°]. The crystal packing is stabilized by intra-molecular and inter-molecular N-H⋯O hydrogen-bonding inter-actions.

Related literature

For related coordination compounds of 2-amino-3-methyl­pyridine, see: Arab Ahmadi et al. (2011 ▶); Tadjarodi et al. (2010 ▶, 2012 ▶); Castillo et al. (2001 ▶); Ziegler et al. (2000 ▶); Amani Komaei et al. (1999 ▶); Chen et al. (2005 ▶). For proton-transfer compounds of 2-amino-3-methyl­pyridine, see: Carnevale et al. (2010 ▶).

Experimental

Crystal data

[Co(C2H3O2)2(C6H8N2)2]

M = 393.31

Triclinic,

a = 8.1685 (16) Å

b = 10.452 (2) Å

c = 12.231 (2) Å

α = 69.58 (3)°

β = 79.94 (3)°

γ = 72.42 (3)°

V = 930.1 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.95 mm−1

T = 298 K

0.27 × 0.23 × 0.13 mm

Data collection

Stoe IPDS 2T diffractometer

Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005 ▶) T min = 0.785, T max = 0.886

11215 measured reflections

4996 independent reflections

2756 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.096

S = 0.92

4996 reflections

242 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.19 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812038664/xu5616sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038664/xu5616Isup2.hkl

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

[Co(C2H3O2)2(C6H8N2)2]	Z = 2
Mr = 393.31	F(000) = 410
Triclinic, P1	Dx = 1.404 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1685 (16) Å	Cell parameters from 4996 reflections
b = 10.452 (2) Å	θ = 2.2–29.2°
c = 12.231 (2) Å	µ = 0.95 mm−1
α = 69.58 (3)°	T = 298 K
β = 79.94 (3)°	Plate, violet
γ = 72.42 (3)°	0.27 × 0.23 × 0.13 mm
V = 930.1 (4) Å3

Stoe IPDS 2T diffractometer	4996 independent reflections
Radiation source: fine-focus sealed tube	2756 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.062
rotation method scans	θmax = 29.2°, θmin = 2.2°
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005)	h = −11→11
Tmin = 0.785, Tmax = 0.886	k = −14→14
11215 measured reflections	l = −16→16

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 0.92	w = 1/[σ2(Fo2) + (0.0361P)2] where P = (Fo2 + 2Fc2)/3
4996 reflections	(Δ/σ)max = 0.001
242 parameters	Δρmax = 0.35 e Å−3
3 restraints	Δρmin = −0.19 e Å−3

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.

	x	y	z	Uiso*/Ueq
Co1	0.71818 (5)	0.93397 (4)	0.77010 (3)	0.04555 (13)
O1	0.6158 (3)	1.0480 (2)	0.62129 (18)	0.0698 (6)
O2	0.4417 (3)	1.2043 (3)	0.6980 (2)	0.0879 (8)
O3	0.9471 (3)	1.0418 (2)	0.70296 (17)	0.0653 (6)
O4	0.8186 (2)	0.9932 (2)	0.87698 (16)	0.0593 (5)
N1	0.5289 (3)	0.8404 (3)	0.8723 (2)	0.0516 (6)
N2	0.6160 (3)	0.8098 (3)	1.0513 (2)	0.0569 (6)
N3	0.8801 (3)	0.7557 (2)	0.73364 (18)	0.0431 (5)
N4	0.9101 (4)	0.8685 (3)	0.5353 (2)	0.0638 (7)
C1	0.5153 (3)	0.7826 (3)	0.9897 (2)	0.0458 (6)
C2	0.4051 (4)	0.6933 (3)	1.0468 (3)	0.0570 (8)
C3	0.3999 (5)	0.6244 (4)	1.1759 (3)	0.0808 (11)
H3A	0.3216	0.5655	1.1991	0.121*
H3B	0.3618	0.6957	1.2141	0.121*
H3C	0.5130	0.5676	1.1978	0.121*
C4	0.3094 (4)	0.6719 (4)	0.9766 (3)	0.0737 (10)
H4	0.2364	0.6131	1.0110	0.088*
C5	0.3170 (4)	0.7344 (4)	0.8568 (3)	0.0813 (11)
H5	0.2486	0.7206	0.8108	0.098*
C6	0.4280 (4)	0.8170 (4)	0.8083 (3)	0.0684 (9)
H6	0.4350	0.8593	0.7276	0.082*
C7	0.9548 (3)	0.7526 (3)	0.6262 (2)	0.0435 (6)
C8	1.0746 (4)	0.6286 (3)	0.6109 (3)	0.0540 (7)
C9	1.1499 (5)	0.6286 (4)	0.4888 (3)	0.0899 (12)
H9A	1.2360	0.5413	0.4930	0.135*
H9B	1.2013	0.7063	0.4530	0.135*
H9C	1.0602	0.6381	0.4430	0.135*
C10	1.1139 (4)	0.5139 (3)	0.7075 (3)	0.0636 (8)
H10	1.1933	0.4319	0.6997	0.076*
C11	1.0377 (4)	0.5169 (3)	0.8177 (3)	0.0607 (8)
H11	1.0649	0.4385	0.8837	0.073*
C12	0.9222 (4)	0.6381 (3)	0.8255 (2)	0.0521 (7)
H12	0.8689	0.6400	0.8988	0.063*
C13	0.5012 (4)	1.1626 (3)	0.6146 (3)	0.0553 (7)
C14	0.4425 (6)	1.2476 (5)	0.4946 (4)	0.1086 (15)
H14A	0.3280	1.3066	0.5011	0.163*
H14B	0.4430	1.1849	0.4528	0.163*
H14C	0.5191	1.3057	0.4530	0.163*
C15	0.9323 (4)	1.0452 (3)	0.8040 (2)	0.0492 (7)
C16	1.0438 (4)	1.1079 (4)	0.8434 (3)	0.0724 (10)
H16A	1.1267	1.0337	0.8925	0.109*
H16B	0.9738	1.1690	0.8865	0.109*
H16C	1.1027	1.1615	0.7763	0.109*
H2A	0.666 (4)	0.874 (3)	1.016 (3)	0.087*
H4A	0.842 (4)	0.941 (4)	0.545 (3)	0.087*
H2B	0.587 (4)	0.798 (4)	1.1228 (17)	0.087*
H4B	0.960 (4)	0.877 (4)	0.4681 (19)	0.087*

	U11	U22	U33	U12	U13	U23
Co1	0.0517 (2)	0.0480 (2)	0.0384 (2)	−0.01574 (17)	0.00583 (15)	−0.01758 (17)
O1	0.0657 (14)	0.0686 (15)	0.0551 (14)	0.0066 (12)	−0.0049 (10)	−0.0157 (12)
O2	0.1122 (19)	0.0934 (19)	0.0651 (16)	−0.0283 (15)	0.0210 (13)	−0.0454 (15)
O3	0.0945 (15)	0.0705 (15)	0.0374 (12)	−0.0391 (12)	0.0109 (10)	−0.0177 (10)
O4	0.0669 (13)	0.0814 (15)	0.0415 (11)	−0.0407 (11)	0.0106 (9)	−0.0227 (11)
N1	0.0485 (13)	0.0653 (16)	0.0505 (15)	−0.0228 (12)	0.0103 (10)	−0.0300 (13)
N2	0.0629 (16)	0.0674 (18)	0.0432 (15)	−0.0304 (13)	0.0048 (12)	−0.0134 (14)
N3	0.0491 (13)	0.0397 (13)	0.0371 (13)	−0.0156 (10)	0.0050 (10)	−0.0088 (11)
N4	0.090 (2)	0.0453 (16)	0.0374 (15)	−0.0059 (14)	0.0174 (13)	−0.0117 (13)
C1	0.0416 (14)	0.0437 (16)	0.0521 (17)	−0.0121 (12)	0.0104 (12)	−0.0209 (14)
C2	0.0567 (17)	0.0534 (19)	0.062 (2)	−0.0219 (14)	0.0157 (15)	−0.0234 (16)
C3	0.088 (3)	0.077 (3)	0.076 (3)	−0.046 (2)	0.013 (2)	−0.012 (2)
C4	0.073 (2)	0.076 (2)	0.089 (3)	−0.0447 (19)	0.0195 (19)	−0.037 (2)
C5	0.078 (2)	0.112 (3)	0.086 (3)	−0.056 (2)	0.0105 (19)	−0.052 (3)
C6	0.070 (2)	0.096 (3)	0.058 (2)	−0.0366 (19)	0.0070 (16)	−0.039 (2)
C7	0.0474 (15)	0.0409 (16)	0.0431 (16)	−0.0148 (12)	0.0059 (12)	−0.0161 (14)
C8	0.0600 (18)	0.0420 (17)	0.0564 (19)	−0.0130 (14)	0.0082 (14)	−0.0174 (15)
C9	0.116 (3)	0.061 (2)	0.072 (2)	−0.004 (2)	0.030 (2)	−0.030 (2)
C10	0.0599 (19)	0.0438 (18)	0.079 (2)	−0.0070 (15)	0.0005 (17)	−0.0184 (18)
C11	0.0646 (19)	0.0485 (19)	0.057 (2)	−0.0119 (15)	−0.0061 (15)	−0.0034 (15)
C12	0.0559 (17)	0.0555 (19)	0.0431 (17)	−0.0218 (15)	0.0030 (13)	−0.0103 (15)
C13	0.0556 (18)	0.062 (2)	0.0513 (18)	−0.0127 (16)	−0.0026 (14)	−0.0246 (16)
C14	0.135 (4)	0.091 (3)	0.082 (3)	0.021 (3)	−0.048 (3)	−0.030 (2)
C15	0.0570 (17)	0.0450 (17)	0.0443 (17)	−0.0170 (14)	0.0021 (13)	−0.0124 (13)
C16	0.073 (2)	0.093 (3)	0.068 (2)	−0.045 (2)	0.0090 (17)	−0.032 (2)

Co1—O1	1.962 (2)	C4—C5	1.380 (5)
Co1—O3	2.352 (2)	C4—H4	0.9300
Co1—O4	2.0028 (18)	C5—C6	1.359 (4)
Co1—N1	2.072 (2)	C5—H5	0.9300
Co1—N3	2.074 (2)	C6—H6	0.9300
O1—C13	1.265 (4)	C7—C8	1.419 (4)
O2—C13	1.215 (3)	C8—C10	1.360 (4)
O3—C15	1.233 (3)	C8—C9	1.512 (4)
O4—C15	1.277 (3)	C9—H9A	0.9600
N1—C1	1.349 (3)	C9—H9B	0.9600
N1—C6	1.353 (3)	C9—H9C	0.9600
N2—C1	1.354 (4)	C10—C11	1.389 (4)
N2—H2A	0.845 (18)	C10—H10	0.9300
N2—H2B	0.840 (18)	C11—C12	1.354 (4)
N3—C12	1.345 (4)	C11—H11	0.9300
N3—C7	1.355 (3)	C12—H12	0.9300
N4—C7	1.331 (4)	C13—C14	1.501 (5)
N4—H4A	0.83 (3)	C14—H14A	0.9600
N4—H4B	0.839 (18)	C14—H14B	0.9600
C1—C2	1.414 (4)	C14—H14C	0.9600
C2—C4	1.367 (4)	C15—C16	1.492 (4)
C2—C3	1.489 (4)	C16—H16A	0.9600
C3—H3A	0.9600	C16—H16B	0.9600
C3—H3B	0.9600	C16—H16C	0.9600
C3—H3C	0.9600
O1—Co1—O4	129.30 (10)	N1—C6—C5	122.9 (3)
O1—Co1—N1	104.36 (10)	N1—C6—H6	118.5
O4—Co1—N1	105.67 (8)	C5—C6—H6	118.5
O1—Co1—N3	103.15 (9)	N4—C7—N3	118.0 (2)
O4—Co1—N3	112.27 (9)	N4—C7—C8	121.0 (2)
N1—Co1—N3	97.38 (9)	N3—C7—C8	121.0 (3)
O1—Co1—O3	88.36 (9)	C10—C8—C7	117.8 (3)
O4—Co1—O3	58.90 (7)	C10—C8—C9	123.1 (3)
N1—Co1—O3	164.49 (7)	C7—C8—C9	119.1 (3)
N3—Co1—O3	88.12 (8)	C8—C9—H9A	109.5
C13—O1—Co1	119.87 (19)	C8—C9—H9B	109.5
C15—O3—Co1	83.56 (16)	H9A—C9—H9B	109.5
C15—O4—Co1	98.54 (16)	C8—C9—H9C	109.5
C1—N1—C6	118.6 (2)	H9A—C9—H9C	109.5
C1—N1—Co1	127.67 (17)	H9B—C9—H9C	109.5
C6—N1—Co1	112.7 (2)	C8—C10—C11	121.3 (3)
C1—N2—H2A	118 (2)	C8—C10—H10	119.4
C1—N2—H2B	118 (2)	C11—C10—H10	119.4
H2A—N2—H2B	116 (3)	C12—C11—C10	117.7 (3)
C12—N3—C7	118.3 (2)	C12—C11—H11	121.2
C12—N3—Co1	116.71 (17)	C10—C11—H11	121.2
C7—N3—Co1	124.82 (18)	N3—C12—C11	123.9 (3)
C7—N4—H4A	120 (3)	N3—C12—H12	118.0
C7—N4—H4B	123 (3)	C11—C12—H12	118.0
H4A—N4—H4B	116 (4)	O2—C13—O1	123.5 (3)
N1—C1—N2	117.2 (2)	O2—C13—C14	121.0 (3)
N1—C1—C2	121.9 (2)	O1—C13—C14	115.5 (3)
N2—C1—C2	120.9 (3)	C13—C14—H14A	109.5
C4—C2—C1	116.4 (3)	C13—C14—H14B	109.5
C4—C2—C3	122.9 (3)	H14A—C14—H14B	109.5
C1—C2—C3	120.8 (3)	C13—C14—H14C	109.5
C2—C3—H3A	109.5	H14A—C14—H14C	109.5
C2—C3—H3B	109.5	H14B—C14—H14C	109.5
H3A—C3—H3B	109.5	O3—C15—O4	119.0 (2)
C2—C3—H3C	109.5	O3—C15—C16	121.8 (3)
H3A—C3—H3C	109.5	O4—C15—C16	119.2 (2)
H3B—C3—H3C	109.5	C15—C16—H16A	109.5
C2—C4—C5	122.5 (3)	C15—C16—H16B	109.5
C2—C4—H4	118.7	H16A—C16—H16B	109.5
C5—C4—H4	118.7	C15—C16—H16C	109.5
C6—C5—C4	117.6 (3)	H16A—C16—H16C	109.5
C6—C5—H5	121.2	H16B—C16—H16C	109.5
C4—C5—H5	121.2
O4—Co1—O1—C13	−50.1 (3)	Co1—N1—C1—C2	−164.79 (19)
N1—Co1—O1—C13	74.6 (2)	N1—C1—C2—C4	−1.8 (4)
N3—Co1—O1—C13	175.9 (2)	N2—C1—C2—C4	−179.6 (3)
O3—Co1—O1—C13	−96.4 (2)	N1—C1—C2—C3	176.5 (3)
O1—Co1—O3—C15	138.61 (18)	N2—C1—C2—C3	−1.3 (4)
O4—Co1—O3—C15	−0.62 (17)	C1—C2—C4—C5	−0.6 (5)
N1—Co1—O3—C15	−6.9 (4)	C3—C2—C4—C5	−179.0 (3)
N3—Co1—O3—C15	−118.18 (18)	C2—C4—C5—C6	1.7 (6)
O1—Co1—O4—C15	−56.9 (2)	C1—N1—C6—C5	−1.9 (5)
N1—Co1—O4—C15	178.84 (17)	Co1—N1—C6—C5	167.7 (3)
N3—Co1—O4—C15	73.83 (19)	C4—C5—C6—N1	−0.4 (5)
O3—Co1—O4—C15	0.60 (16)	C12—N3—C7—N4	178.7 (2)
O1—Co1—N1—C1	−161.2 (2)	Co1—N3—C7—N4	−6.2 (3)
O4—Co1—N1—C1	−22.5 (2)	C12—N3—C7—C8	−0.1 (4)
N3—Co1—N1—C1	93.1 (2)	Co1—N3—C7—C8	174.98 (19)
O3—Co1—N1—C1	−16.9 (5)	N4—C7—C8—C10	−179.8 (3)
O1—Co1—N1—C6	30.3 (2)	N3—C7—C8—C10	−1.0 (4)
O4—Co1—N1—C6	169.0 (2)	N4—C7—C8—C9	−0.9 (4)
N3—Co1—N1—C6	−75.3 (2)	N3—C7—C8—C9	177.9 (3)
O3—Co1—N1—C6	174.6 (3)	C7—C8—C10—C11	0.9 (4)
O1—Co1—N3—C12	−157.47 (18)	C9—C8—C10—C11	−177.9 (3)
O4—Co1—N3—C12	59.53 (19)	C8—C10—C11—C12	0.2 (4)
N1—Co1—N3—C12	−50.79 (19)	C7—N3—C12—C11	1.3 (4)
O3—Co1—N3—C12	114.65 (18)	Co1—N3—C12—C11	−174.1 (2)
O1—Co1—N3—C7	27.4 (2)	C10—C11—C12—N3	−1.4 (4)
O4—Co1—N3—C7	−115.6 (2)	Co1—O1—C13—O2	−4.2 (4)
N1—Co1—N3—C7	134.1 (2)	Co1—O1—C13—C14	175.0 (3)
O3—Co1—N3—C7	−60.5 (2)	Co1—O3—C15—O4	0.9 (3)
C6—N1—C1—N2	−179.0 (3)	Co1—O3—C15—C16	−179.2 (3)
Co1—N1—C1—N2	13.1 (4)	Co1—O4—C15—O3	−1.1 (3)
C6—N1—C1—C2	3.1 (4)	Co1—O4—C15—C16	179.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4	0.85 (2)	2.17 (2)	2.965 (3)	157 (3)
N2—H2B···O2i	0.84 (2)	2.16 (2)	2.978 (3)	166 (3)
N4—H4A···O1	0.83 (3)	2.10 (3)	2.859 (3)	153 (3)
N4—H4B···O3ii	0.84 (2)	2.06 (2)	2.881 (3)	164 (3)

Table 1

Selected bond lengths (Å)

Co1—O1	1.962 (2)
Co1—O3	2.352 (2)
Co1—O4	2.0028 (18)
Co1—N1	2.072 (2)
Co1—N3	2.074 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O4	0.85 (2)	2.17 (2)	2.965 (3)	157 (3)
N2—H2B⋯O2i	0.84 (2)	2.16 (2)	2.978 (3)	166 (3)
N4—H4A⋯O1	0.83 (3)	2.10 (3)	2.859 (3)	153 (3)
N4—H4B⋯O3ii	0.84 (2)	2.06 (2)	2.881 (3)	164 (3)

Symmetry codes: (i) ; (ii) .