(Acetato-κ2O,O′)(acetato-κO)bis(2-amino-3-methyl­pyridine-κN1)cobalt(II)

Tadjarodi, A.; Bijanzad, K.; Notash, B.

doi:10.1107/S1600536812038664

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Pages m1260-m1261

https://doi.org/10.1107/S1600536812038664

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(Acetato-κ²O,O′)(acetato-κO)bis(2-amino-3-methylpyridine-κN¹)cobalt(II)

Azadeh Tadjarodi,^a ^* Keyvan Bijanzad ^a and Behrouz Notash ^b

^aDepartment of Chemistry, Iran University of Science and Technology, Tehran 16846-13114, Iran, and ^bDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran
^*Correspondence e-mail: tajarodi@iust.ac.ir

(Received 1 September 2012; accepted 9 September 2012; online 15 September 2012)

In the title compound, [Co(CH₃COO)₂(C₆H₈N₂)₂], the Co^II ion is five-coordinated by two pyridine N atoms from two 2-amino-3-methylpyridine 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 intramolecular and intermolecular N—H⋯O hydrogen-bonding interactions.

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_r = 393.31
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.051
wR(F²) = 0.096
S = 0.92
4996 reflections
242 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.19 e Å⁻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) -x+1, -y+2, -z+2; (ii) -x+2, -y+2, -z+1.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812038664/xu5616sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812038664/xu5616Isup2.hkl

checkCIF report

Comment top

2-Amino-3-methylpyridine (ampy) coordinates to metals mostly through the nitrogen atom of the pyridyl group (Arab Ahmadi et al., 2011; Tadjarodi et al., 2012 and 2010; Castillo et al., 2001; Ziegler et al., 2000; Amani Komaei et al., 1999) but it can also coordinate via the nitrogen atom of the amino group (Chen et al., 2005). In recent years, several structures of proton-transfer compounds, [(ampyH)₂CoX₄] (X = Cl, Br) have been reported by 2-Amino-3-methylpyridine (Carnevale et al. 2010).

Herein, we report the synthesis and structural determination of the title compound, [Co(ampy)₂(CH₃COO)₂]. The coordination sphere of the mononuclear complex includes three oxygen atoms from two acetate ions and two pyridyl nitrogen atoms from two ampy ligands thus constructing a distorted trigonal bipyramidal geometry (Fig. 1). In the structure of [Co(ampy)₂(CH₃COO)₂], several intramolecular and intermolecular N–H···O hydrogen bond interactions formed between the amino group of the ligand and the acetate oxygen atoms which can stabilize the crystal structure (Fig. 2 & Table 1).

Related literature top

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 top

A solution of 2-amino-3-methylpyridine (1 mmol) in ethanol was added to an aqueous solution of Co(CH₃COO)₂.4H₂O (0.5 mmol) and stirred for 20 min at 50 °C. Slow evaporation of the resulting solution gave violet plate shaped crystals of the title compound suitable for X-ray analysis (decomposition >300 °C).

Structure description top

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).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); 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).

Figures top

	Fig. 1. The molecular structure of [Co(ampy)₂(CH₃COO)₂] with displacement ellipsoids drawn at 30% probability level.
	Fig. 2. The packing diagram of the title compound showing hydrogen bonding as blue dashed lines.

(Acetato-κ²O,O')(acetato-κO)bis(2-amino-3- methylpyridine-κN¹)cobalt(II) top

Crystal data top

[Co(C₂H₃O₂)₂(C₆H₈N₂)₂]	Z = 2
M_r = 393.31	F(000) = 410
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0361P)²] where P = (F_o² + 2F_c²)/3
4996 reflections	(Δ/σ)_max = 0.001
242 parameters	Δρ_max = 0.35 e Å⁻³
3 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

[Co(C₂H₃O₂)₂(C₆H₈N₂)₂]	γ = 72.42 (3)°
M_r = 393.31	V = 930.1 (4) Å³
Triclinic, P1	Z = 2
a = 8.1685 (16) Å	Mo Kα radiation
b = 10.452 (2) Å	µ = 0.95 mm⁻¹
c = 12.231 (2) Å	T = 298 K
α = 69.58 (3)°	0.27 × 0.23 × 0.13 mm
β = 79.94 (3)°

Data collection top

Stoe IPDS 2T diffractometer	4996 independent reflections
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005)	2756 reflections with I > 2σ(I)
T_min = 0.785, T_max = 0.886	R_int = 0.062
11215 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	3 restraints
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 0.92	Δρ_max = 0.35 e Å⁻³
4996 reflections	Δρ_min = −0.19 e Å⁻³
242 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+2, −z+2; (ii) −x+2, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	[Co(C₂H₃O₂)₂(C₆H₈N₂)₂]
M_r	393.31
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.1685 (16), 10.452 (2), 12.231 (2)
α, β, γ (°)	69.58 (3), 79.94 (3), 72.42 (3)
V (Å³)	930.1 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.95
Crystal size (mm)	0.27 × 0.23 × 0.13

Data collection
Diffractometer	Stoe IPDS 2T
Absorption correction	Numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005)
T_min, T_max	0.785, 0.886
No. of measured, independent and observed [I > 2σ(I)] reflections	11215, 4996, 2756
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.687

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.096, 0.92
No. of reflections	4996
No. of parameters	242
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.19

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4	0.845 (18)	2.17 (2)	2.965 (3)	157 (3)
N2—H2B···O2ⁱ	0.840 (18)	2.156 (19)	2.978 (3)	166 (3)
N4—H4A···O1	0.83 (3)	2.10 (3)	2.859 (3)	153 (3)
N4—H4B···O3ⁱⁱ	0.839 (18)	2.06 (2)	2.881 (3)	164 (3)

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

Acknowledgements

The authors wish to acknowledge Iran University of Science and Technology (IUST) for financial support.

References

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