Abstract
In the title compound, [Co(CH3COO)2(C6H8N2)2], the CoII 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,
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 ▶).
Supplementary Material
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
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)
.
Acknowledgments
The authors wish to acknowledge Iran University of Science and Technology (IUST) for financial support.
supplementary crystallographic information
Comment
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).
Experimental
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).
Refinement
Hydrogen atoms attached to nitrogen atoms were found in difference Fourier map.H2A and H2B and H4B were refined with distance restraints of N—H 0.845 (18), 0.840 (18) and 0.839 (18), respectively. H atoms attached to carbon atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 Å (CH), with C—H = 0.96 Å (CH3), and Uiso(H) = 1.2,1.5Ueq(C).
Figures
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.
Crystal data
| [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 |
Data collection
| 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
| 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 |
Special details
| 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)
| 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* |
Atomic displacement parameters (Å2)
| 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)
| 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)
| 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.
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5616).
References
- Amani Komaei, S., Van Albada, G. A., Mutikainen, I., Turpeinen, U. & Reedijk, J. (1999). Polyhedron, 18, 1991–1997.
- Arab Ahmadi, R., Safari, N., Khavasi, H. R. & Amani, S. (2011). J. Coord. Chem. 64, 2056–2065.
- Carnevale, D. J., Landee, C. P., Turnbull, M. M., Winn, M. & Xiao, F. (2010). J. Coord. Chem. 63, 2223–2238.
- Castillo, O., Luque, A., Lloret, F. & Román, P. (2001). Inorg. Chem. Commun. 4, 350–353.
- Chen, Z.-F., Liu, B., Liang, H., Hu, R.-X. & Zhou, Z.-Y. (2005). J. Coord. Chem. 28, 561–565.
- Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
- Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.
- Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
- Stoe & Cie (2005). X-AREA, X-RED32 and X-SHAPE Stoe & Cie, Darmstadt, Germany.
- Tadjarodi, A., Bijanzad, K. & Notash, B. (2010). Acta Cryst. E66, m1293–m1294. [DOI] [PMC free article] [PubMed]
- Tadjarodi, A., Bijanzad, K. & Notash, B. (2012). Acta Cryst. E68, m1099. [DOI] [PMC free article] [PubMed]
- Ziegler, C. J., Silverman, A. P. & Lippard, S. J. (2000). J. Biol. Inorg. Chem. 5, 774–783. [DOI] [PubMed]
Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
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


