metal-organic compounds
Bis(2-amino-3-methylpyridine)dichloridocobalt(II)
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
In the title compound, [CoCl2(C6H8N2)2], the CoII ion is four-coordinated by two pyridine N atoms from the 2-amino-3-methylpyridine ligands and two chloride ions in a distorted tetrahedral geometry. A weak intramolecular N—H⋯Cl interaction occurs. The crystal packing is stabilized by intermolecular N—H⋯Cl and C—H⋯Cl hydrogen-bond interactions.
Related literature
2-Amino-3-methylpyridine (ampy) can potentially coordinate to metal centers through the N atom of the amino group (Chen et al., 2005) or the pyridyl nitrogen atom (Amani Komaei et al., 1999; Ziegler et al., 2000; Castillo et al., 2001). For the structures of [(ampyH)2CoX4] proton-transfer compounds (X = Cl, Br), see: Carnevale et al. (2010). Polar metal–halogen bonds are good hydrogen-bond acceptors, see: Aullón et al. (1998).
Experimental
Crystal data
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Refinement
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Data collection: X-AREA (Stoe & Cie, 2005); cell 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
10.1107/S1600536810036597/jj2058sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536810036597/jj2058Isup2.hkl
A solution of 2-amino-3-methylpyridine (0.1 ml, 1 mmol) in ethanol (10 ml) was added to a solution of CoCl2.6H2O (0.12 g, 0.5 mmol) in water (10 ml) and stirred for 20 min at 50 °C. Slow evaporation of the resulting solution gave a blue precipitate which was then recrystallized from ethanol and acetonitrile (3:1 v/v). After one week, blue crystals of the title compound suitable for X-ray analysis were isolated (yield; 0.1583 g, 91.4% based on Co, decomposition > 168 °C).
All of the H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93Å (CH), with C—H = 0.96Å (CH3), and Uiso(H) = 1.2, 1.49Ueq(C), and with N—H = 0.86Å (NH2) and Uiso(H) = 1.2Ueq(N).
Data collection: X-AREA (Stoe & Cie, 2005); cell
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).[CoCl2(C6H8N2)2] | F(000) = 708.0 |
Mr = 346.12 | Dx = 1.479 Mg m−3 |
Monoclinic, P21/n | Melting point: 441 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 9.3768 (19) Å | Cell parameters from 4174 reflections |
b = 13.841 (3) Å | θ = 2.3–29.2° |
c = 12.175 (2) Å | µ = 1.44 mm−1 |
β = 100.31 (3)° | T = 298 K |
V = 1554.6 (5) Å3 | Block, blue |
Z = 4 | 0.5 × 0.38 × 0.3 mm |
Stoe IPDS II diffractometer | 4174 independent reflections |
Radiation source: fine-focus sealed tube | 2803 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
Detector resolution: 0.15 pixels mm-1 | θmax = 29.2°, θmin = 2.3° |
rotation method scans | h = −12→10 |
Absorption correction: numerical shape of crystal determined optically (X-RED and X-SHAPE; Stoe & Cie, 2005) | k = −18→18 |
Tmin = 0.517, Tmax = 0.642 | l = −16→16 |
11996 measured reflections |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0528P)2 + 0.6654P] where P = (Fo2 + 2Fc2)/3 |
4174 reflections | (Δ/σ)max = 0.001 |
174 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.52 e Å−3 |
[CoCl2(C6H8N2)2] | V = 1554.6 (5) Å3 |
Mr = 346.12 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.3768 (19) Å | µ = 1.44 mm−1 |
b = 13.841 (3) Å | T = 298 K |
c = 12.175 (2) Å | 0.5 × 0.38 × 0.3 mm |
β = 100.31 (3)° |
Stoe IPDS II diffractometer | 4174 independent reflections |
Absorption correction: numerical shape of crystal determined optically (X-RED and X-SHAPE; Stoe & Cie, 2005) | 2803 reflections with I > 2σ(I) |
Tmin = 0.517, Tmax = 0.642 | Rint = 0.055 |
11996 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | 0 restraints |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.47 e Å−3 |
4174 reflections | Δρmin = −0.52 e Å−3 |
174 parameters |
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 | 0.14951 (4) | 0.99824 (3) | 0.31175 (3) | 0.04765 (14) | |
Cl2 | 0.09365 (12) | 1.14810 (7) | 0.35642 (8) | 0.0730 (3) | |
Cl1 | 0.24844 (11) | 0.99925 (9) | 0.15526 (7) | 0.0738 (3) | |
N3 | 0.2899 (3) | 0.93750 (18) | 0.43978 (19) | 0.0450 (6) | |
N1 | −0.0296 (3) | 0.9120 (2) | 0.2839 (2) | 0.0484 (6) | |
C5 | −0.0369 (4) | 0.8380 (3) | 0.3553 (3) | 0.0579 (8) | |
H5 | 0.0376 | 0.8310 | 0.4164 | 0.069* | |
C1 | −0.1395 (3) | 0.9237 (3) | 0.1967 (2) | 0.0509 (7) | |
C7 | 0.3589 (3) | 0.8548 (2) | 0.4302 (3) | 0.0490 (7) | |
C2 | −0.2593 (4) | 0.8599 (3) | 0.1783 (3) | 0.0552 (8) | |
C9 | 0.4738 (4) | 0.8617 (3) | 0.6192 (3) | 0.0641 (9) | |
H9 | 0.5363 | 0.8367 | 0.6805 | 0.077* | |
C11 | 0.3132 (4) | 0.9843 (2) | 0.5399 (3) | 0.0541 (8) | |
H11 | 0.2654 | 1.0423 | 0.5464 | 0.065* | |
C6 | −0.3807 (4) | 0.8754 (4) | 0.0808 (3) | 0.0829 (13) | |
H6A | −0.4567 | 0.8296 | 0.0844 | 0.124* | |
H6B | −0.3449 | 0.8665 | 0.0124 | 0.124* | |
H6C | −0.4179 | 0.9398 | 0.0835 | 0.124* | |
C8 | 0.4538 (4) | 0.8119 (3) | 0.5215 (3) | 0.0546 (8) | |
N2 | −0.1321 (4) | 0.9997 (2) | 0.1281 (3) | 0.0756 (10) | |
H2A | −0.0593 | 1.0385 | 0.1409 | 0.091* | |
H2B | −0.2003 | 1.0093 | 0.0718 | 0.091* | |
C10 | 0.4044 (4) | 0.9485 (3) | 0.6308 (3) | 0.0664 (10) | |
H10 | 0.4195 | 0.9814 | 0.6985 | 0.080* | |
C3 | −0.2594 (4) | 0.7855 (3) | 0.2517 (3) | 0.0680 (10) | |
H3 | −0.3359 | 0.7418 | 0.2410 | 0.082* | |
C4 | −0.1470 (4) | 0.7738 (3) | 0.3422 (3) | 0.0705 (10) | |
H4 | −0.1477 | 0.7232 | 0.3923 | 0.085* | |
N4 | 0.3322 (4) | 0.8108 (3) | 0.3292 (3) | 0.0793 (10) | |
H4A | 0.2730 | 0.8365 | 0.2749 | 0.095* | |
H4B | 0.3745 | 0.7572 | 0.3193 | 0.095* | |
C12 | 0.5285 (5) | 0.7188 (3) | 0.5056 (4) | 0.0809 (12) | |
H12A | 0.5894 | 0.7005 | 0.5744 | 0.121* | |
H12B | 0.5866 | 0.7267 | 0.4488 | 0.121* | |
H12C | 0.4574 | 0.6693 | 0.4833 | 0.121* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.0456 (2) | 0.0545 (2) | 0.0391 (2) | −0.0008 (2) | −0.00267 (15) | 0.00612 (18) |
Cl2 | 0.0862 (7) | 0.0581 (5) | 0.0698 (5) | 0.0198 (5) | 0.0008 (5) | 0.0085 (4) |
Cl1 | 0.0666 (5) | 0.1115 (8) | 0.0421 (4) | −0.0138 (6) | 0.0066 (4) | 0.0074 (5) |
N3 | 0.0440 (13) | 0.0488 (14) | 0.0392 (12) | 0.0019 (11) | −0.0004 (10) | 0.0034 (10) |
N1 | 0.0436 (14) | 0.0585 (15) | 0.0405 (12) | −0.0034 (11) | 0.0005 (10) | 0.0044 (11) |
C5 | 0.0514 (18) | 0.075 (2) | 0.0442 (16) | −0.0008 (17) | 0.0012 (14) | 0.0128 (15) |
C1 | 0.0452 (16) | 0.0637 (19) | 0.0419 (15) | −0.0024 (14) | 0.0024 (13) | 0.0021 (14) |
C7 | 0.0448 (16) | 0.0516 (17) | 0.0499 (16) | −0.0021 (14) | 0.0059 (13) | −0.0013 (14) |
C2 | 0.0454 (16) | 0.076 (2) | 0.0431 (16) | −0.0095 (16) | 0.0038 (13) | 0.0002 (15) |
C9 | 0.058 (2) | 0.078 (2) | 0.0525 (19) | 0.0033 (18) | −0.0009 (16) | 0.0191 (18) |
C11 | 0.0531 (17) | 0.060 (2) | 0.0454 (15) | −0.0001 (15) | −0.0011 (13) | −0.0006 (14) |
C6 | 0.057 (2) | 0.121 (4) | 0.062 (2) | −0.025 (2) | −0.0139 (18) | 0.015 (2) |
C8 | 0.0425 (15) | 0.0540 (18) | 0.066 (2) | −0.0001 (14) | 0.0062 (14) | 0.0155 (16) |
N2 | 0.0690 (19) | 0.082 (2) | 0.0641 (18) | −0.0192 (17) | −0.0205 (15) | 0.0253 (17) |
C10 | 0.070 (2) | 0.084 (3) | 0.0393 (16) | −0.002 (2) | −0.0054 (15) | −0.0015 (17) |
C3 | 0.056 (2) | 0.086 (3) | 0.061 (2) | −0.023 (2) | 0.0079 (16) | 0.0053 (19) |
C4 | 0.059 (2) | 0.085 (3) | 0.065 (2) | −0.015 (2) | 0.0053 (17) | 0.024 (2) |
N4 | 0.093 (2) | 0.075 (2) | 0.0648 (19) | 0.0253 (19) | −0.0001 (17) | −0.0170 (16) |
C12 | 0.074 (3) | 0.067 (2) | 0.102 (3) | 0.019 (2) | 0.016 (2) | 0.019 (2) |
Co1—N3 | 2.034 (2) | C9—H9 | 0.9300 |
Co1—N1 | 2.038 (3) | C11—C10 | 1.365 (5) |
Co1—Cl2 | 2.2303 (11) | C11—H11 | 0.9300 |
Co1—Cl1 | 2.2635 (11) | C6—H6A | 0.9600 |
N3—C7 | 1.330 (4) | C6—H6B | 0.9600 |
N3—C11 | 1.363 (4) | C6—H6C | 0.9600 |
N1—C1 | 1.350 (4) | C8—C12 | 1.495 (6) |
N1—C5 | 1.353 (4) | N2—H2A | 0.8600 |
C5—C4 | 1.349 (5) | N2—H2B | 0.8600 |
C5—H5 | 0.9300 | C10—H10 | 0.9300 |
C1—N2 | 1.352 (4) | C3—C4 | 1.391 (5) |
C1—C2 | 1.415 (5) | C3—H3 | 0.9300 |
C7—N4 | 1.355 (4) | C4—H4 | 0.9300 |
C7—C8 | 1.424 (4) | N4—H4A | 0.8600 |
C2—C3 | 1.363 (5) | N4—H4B | 0.8600 |
C2—C6 | 1.506 (5) | C12—H12A | 0.9600 |
C9—C8 | 1.358 (5) | C12—H12B | 0.9600 |
C9—C10 | 1.385 (6) | C12—H12C | 0.9600 |
N3—Co1—N1 | 106.66 (10) | C2—C6—H6A | 109.5 |
N3—Co1—Cl2 | 110.23 (8) | C2—C6—H6B | 109.5 |
N1—Co1—Cl2 | 111.26 (9) | H6A—C6—H6B | 109.5 |
N3—Co1—Cl1 | 109.94 (8) | C2—C6—H6C | 109.5 |
N1—Co1—Cl1 | 108.24 (8) | H6A—C6—H6C | 109.5 |
Cl2—Co1—Cl1 | 110.42 (5) | H6B—C6—H6C | 109.5 |
C7—N3—C11 | 119.0 (3) | C9—C8—C7 | 116.1 (3) |
C7—N3—Co1 | 123.1 (2) | C9—C8—C12 | 123.8 (3) |
C11—N3—Co1 | 117.8 (2) | C7—C8—C12 | 120.0 (3) |
C1—N1—C5 | 118.5 (3) | C1—N2—H2A | 120.0 |
C1—N1—Co1 | 123.4 (2) | C1—N2—H2B | 120.0 |
C5—N1—Co1 | 118.1 (2) | H2A—N2—H2B | 120.0 |
C4—C5—N1 | 123.2 (3) | C11—C10—C9 | 118.0 (3) |
C4—C5—H5 | 118.4 | C11—C10—H10 | 121.0 |
N1—C5—H5 | 118.4 | C9—C10—H10 | 121.0 |
N1—C1—N2 | 117.6 (3) | C2—C3—C4 | 121.1 (3) |
N1—C1—C2 | 121.4 (3) | C2—C3—H3 | 119.4 |
N2—C1—C2 | 121.0 (3) | C4—C3—H3 | 119.4 |
N3—C7—N4 | 117.0 (3) | C5—C4—C3 | 118.2 (3) |
N3—C7—C8 | 122.4 (3) | C5—C4—H4 | 120.9 |
N4—C7—C8 | 120.6 (3) | C3—C4—H4 | 120.9 |
C3—C2—C1 | 117.5 (3) | C7—N4—H4A | 120.0 |
C3—C2—C6 | 122.3 (3) | C7—N4—H4B | 120.0 |
C1—C2—C6 | 120.2 (3) | H4A—N4—H4B | 120.0 |
C8—C9—C10 | 122.4 (3) | C8—C12—H12A | 109.5 |
C8—C9—H9 | 118.8 | C8—C12—H12B | 109.5 |
C10—C9—H9 | 118.8 | H12A—C12—H12B | 109.5 |
N3—C11—C10 | 122.0 (3) | C8—C12—H12C | 109.5 |
N3—C11—H11 | 119.0 | H12A—C12—H12C | 109.5 |
C10—C11—H11 | 119.0 | H12B—C12—H12C | 109.5 |
N1—Co1—N3—C7 | 69.9 (3) | C11—N3—C7—C8 | 1.6 (5) |
Cl2—Co1—N3—C7 | −169.2 (2) | Co1—N3—C7—C8 | −178.2 (2) |
Cl1—Co1—N3—C7 | −47.3 (3) | N1—C1—C2—C3 | −0.4 (5) |
N1—Co1—N3—C11 | −109.9 (2) | N2—C1—C2—C3 | −179.4 (4) |
Cl2—Co1—N3—C11 | 11.0 (3) | N1—C1—C2—C6 | 179.5 (4) |
Cl1—Co1—N3—C11 | 133.0 (2) | N2—C1—C2—C6 | 0.5 (6) |
N3—Co1—N1—C1 | −172.4 (3) | C7—N3—C11—C10 | −0.4 (5) |
Cl2—Co1—N1—C1 | 67.4 (3) | Co1—N3—C11—C10 | 179.3 (3) |
Cl1—Co1—N1—C1 | −54.1 (3) | C10—C9—C8—C7 | 1.1 (5) |
N3—Co1—N1—C5 | 6.1 (3) | C10—C9—C8—C12 | 179.1 (4) |
Cl2—Co1—N1—C5 | −114.1 (2) | N3—C7—C8—C9 | −1.9 (5) |
Cl1—Co1—N1—C5 | 124.4 (2) | N4—C7—C8—C9 | 179.8 (4) |
C1—N1—C5—C4 | 1.6 (5) | N3—C7—C8—C12 | −180.0 (3) |
Co1—N1—C5—C4 | −176.9 (3) | N4—C7—C8—C12 | 1.8 (5) |
C5—N1—C1—N2 | 178.2 (3) | N3—C11—C10—C9 | −0.3 (6) |
Co1—N1—C1—N2 | −3.3 (4) | C8—C9—C10—C11 | −0.1 (6) |
C5—N1—C1—C2 | −0.9 (5) | C1—C2—C3—C4 | 1.1 (6) |
Co1—N1—C1—C2 | 177.6 (2) | C6—C2—C3—C4 | −178.9 (4) |
C11—N3—C7—N4 | 179.9 (3) | N1—C5—C4—C3 | −1.0 (6) |
Co1—N3—C7—N4 | 0.1 (4) | C2—C3—C4—C5 | −0.4 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···Cl1i | 0.86 | 2.72 | 3.427 (4) | 140 |
N4—H4A···Cl1 | 0.86 | 2.67 | 3.363 (4) | 138 |
N4—H4B···Cl2ii | 0.86 | 2.68 | 3.350 (4) | 136 |
C3—H3···Cl2iii | 0.93 | 2.81 | 3.701 (4) | 161 |
Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x−1/2, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [CoCl2(C6H8N2)2] |
Mr | 346.12 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 9.3768 (19), 13.841 (3), 12.175 (2) |
β (°) | 100.31 (3) |
V (Å3) | 1554.6 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.44 |
Crystal size (mm) | 0.5 × 0.38 × 0.3 |
Data collection | |
Diffractometer | Stoe IPDS II diffractometer |
Absorption correction | Numerical shape of crystal determined optically (X-RED and X-SHAPE; Stoe & Cie, 2005) |
Tmin, Tmax | 0.517, 0.642 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11996, 4174, 2803 |
Rint | 0.055 |
(sin θ/λ)max (Å−1) | 0.686 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.132, 1.07 |
No. of reflections | 4174 |
No. of parameters | 174 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.47, −0.52 |
Computer programs: X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
Co1—N3 | 2.034 (2) | Co1—Cl2 | 2.2303 (11) |
Co1—N1 | 2.038 (3) | Co1—Cl1 | 2.2635 (11) |
N3—Co1—N1 | 106.66 (10) | N3—Co1—Cl1 | 109.94 (8) |
N3—Co1—Cl2 | 110.23 (8) | N1—Co1—Cl1 | 108.24 (8) |
N1—Co1—Cl2 | 111.26 (9) | Cl2—Co1—Cl1 | 110.42 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···Cl1i | 0.86 | 2.72 | 3.427 (4) | 140 |
N4—H4A···Cl1 | 0.86 | 2.67 | 3.363 (4) | 138 |
N4—H4B···Cl2ii | 0.86 | 2.68 | 3.350 (4) | 136 |
C3—H3···Cl2iii | 0.93 | 2.81 | 3.701 (4) | 161 |
Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x−1/2, y−1/2, −z+1/2. |
Acknowledgements
The authors wish to acknowledge Iran University of Science and Technology (IUST) for financial support.
References
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2-amino-3-methylpyridine (ampy) is a common ligand and potentially can coordinate to metal centers through the N atom of amino group (Chen et al., 2005) or the pyridyl nitrogen atom (Amani Komaei et al., 1999; Ziegler et al., 2000; Castillo et al., 2001). Recently, the structure of [(ampyH)2CoX4] proton transfer compounds (X=Cl, Br) have been reported (Carnevale et al., 2010). Polar metal-halogen bonds are good hydrogen bond acceptors (Aullón et al., 1998). We report herein the synthesis and molecular structure of the title compound, [Co(ampy)2Cl2]. The compound is mononuclear with the cobalt (II) ion coordinated by two pyridyl nitrogen atoms from two ampy ligands and two chloride ions in a distorted tetrahedral geometry (Fig. 1). The Co—N and Co—Cl bond lengths and angles are within normal ranges (Table 1). The dihedral angle formed between the least squares planes of two pyridine rings is 69.5 (5)°. Crystal packing is stabilized by weak intramolecular N–H···Cl and intermolecular N—H···Cl, C—H···Cl hydrogen bond interactions (Table 2). Cl1 forms a bifurcated acceptor bond with H4A and H2B from nearby neighbors (Fig. 2).