metal-organic compounds
Dichlorido[N′-(3,5-dichloro-2-hydroxybenzylidene)pyridine-4-carbohydrazide-κN](1,10-phenanthroline-κ2N,N′)cobalt(II) methanol monosolvate
aKey Laboratory of Nonferrous Metal Materials and Processing Technology, Department of Material and Chemical Engineering, Guilin University of Technology, Ministry of Education, Guilin 541004, People's Republic of China, and College of Chemical and Biological Engineering, Guilin University of Technology, Guilin 541004, People's Republic of China
*Correspondence e-mail: lisa4.6@163.com
In the title compound, [CoCl2(C13H9Cl2N3O2)2(C12H8N2)]·CH3OH, the CoII atom is octahedrally coordinated by two N atoms from the pyridyl rings of the tridentate N′-(3,5-dichloro-2-hydroxybenzylidene)pyridine-4-carbohydrazide (H2L) ligand, two N atoms from the 1,10-phenanthroline ligand and two chloride ions. The acylhydrazone groups are not involved into the coordination of the metal ion. In the crystal packing an extended three-dimensional network formed by N—H⋯Cl, N—H⋯O, O—H⋯N, O—H⋯N and O—H⋯Cl hydrogen bonds is observed.
Related literature
For acylhydrazone complexes containing heteroatoms, see: Adams et al. (2000); Kuriakose et al. (2007); Lobana et al. (2006); Mujeebur Rahman et al. (2005). For a related structure, see: Armstrong et al. (2003).
Experimental
Crystal data
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Data collection: SMART (Bruker, 2001); cell SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536809047680/vm2009sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809047680/vm2009Isup2.hkl
An EtOH solution (30 ml) of 3,5-Dichlorosalicylaldehyde (10 mmol) was added dropwise to the EtOH solution (20 ml) of 4-Pyridinecarboxylic acid hydrazide (10 mmol) with stirring at ca 75\ % C for 3 h. The white precipitates was removed by filtration and recrystallized from EtOH solution. Then a mixture of the ligand (0.5 mmol) and cobalt chloride (0.5 mmol) in MeOH (35 ml) was stirred at ca 65\ % C for 45 min to give the red precipitates. Add 10 ml MeOH solution of 1,10-phenanthroline (0.5 mmol) to the mixture and stirred for 1.5 h. The red precipitate decreased gradually. Then the mixture was filtrated and ether evaporated slowly to afford almost quantitatively red crystals of mononuclear complex at ambient temperature after several days.
Data collection: SMART (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).[CoCl2(C13H9Cl2N3O2)2(C12H8N2)]·CH4O | F(000) = 1956 |
Mr = 962.34 | Dx = 1.573 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 3420 reflections |
a = 20.797 (3) Å | θ = 2.3–25.2° |
b = 14.1641 (16) Å | µ = 0.87 mm−1 |
c = 13.7952 (10) Å | T = 298 K |
V = 4063.7 (7) Å3 | Block, red |
Z = 4 | 0.32 × 0.23 × 0.22 mm |
Bruker SMART CCD area-detector diffractometer | 7003 independent reflections |
Radiation source: fine-focus sealed tube | 3870 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −16→24 |
Tmin = 0.768, Tmax = 0.831 | k = −16→15 |
17533 measured reflections | l = −15→16 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.056 | H-atom parameters constrained |
wR(F2) = 0.170 | w = 1/[σ2(Fo2) + (0.0742P)2 + 2.7173P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
7003 reflections | Δρmax = 0.51 e Å−3 |
532 parameters | Δρmin = −0.57 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 3259 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.50 (3) |
[CoCl2(C13H9Cl2N3O2)2(C12H8N2)]·CH4O | V = 4063.7 (7) Å3 |
Mr = 962.34 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 20.797 (3) Å | µ = 0.87 mm−1 |
b = 14.1641 (16) Å | T = 298 K |
c = 13.7952 (10) Å | 0.32 × 0.23 × 0.22 mm |
Bruker SMART CCD area-detector diffractometer | 7003 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3870 reflections with I > 2σ(I) |
Tmin = 0.768, Tmax = 0.831 | Rint = 0.052 |
17533 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | H-atom parameters constrained |
wR(F2) = 0.170 | Δρmax = 0.51 e Å−3 |
S = 1.03 | Δρmin = −0.57 e Å−3 |
7003 reflections | Absolute structure: Flack (1983), 3259 Friedel pairs |
532 parameters | Absolute structure parameter: 0.50 (3) |
1 restraint |
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 | 0.00635 (5) | 0.61639 (7) | 0.39038 (8) | 0.0510 (3) | |
Cl1 | 0.05943 (11) | 0.47788 (16) | 0.32986 (17) | 0.0678 (6) | |
Cl2 | −0.06639 (11) | 0.53739 (18) | 0.50061 (16) | 0.0687 (6) | |
Cl3 | −0.44946 (12) | 0.6158 (2) | −0.3164 (2) | 0.0958 (9) | |
Cl4 | −0.26296 (14) | 0.6306 (2) | −0.57949 (18) | 0.1032 (10) | |
Cl5 | 0.48041 (14) | 0.6604 (3) | 1.0861 (2) | 0.1090 (11) | |
Cl6 | 0.28736 (17) | 0.6082 (2) | 1.3338 (2) | 0.1105 (11) | |
N1 | −0.0618 (3) | 0.6114 (4) | 0.2669 (5) | 0.0461 (16) | |
N2 | −0.1804 (3) | 0.6209 (4) | −0.0562 (5) | 0.0560 (18) | |
H2 | −0.1402 | 0.6179 | −0.0707 | 0.067* | |
N3 | −0.2272 (3) | 0.6245 (4) | −0.1259 (4) | 0.0526 (17) | |
N4 | 0.0816 (3) | 0.6290 (4) | 0.5052 (5) | 0.0532 (17) | |
N5 | 0.2138 (4) | 0.6320 (5) | 0.8120 (5) | 0.066 (2) | |
H5 | 0.1740 | 0.6326 | 0.8289 | 0.079* | |
N6 | 0.2631 (3) | 0.6351 (5) | 0.8798 (5) | 0.0615 (18) | |
N7 | −0.0302 (3) | 0.7527 (5) | 0.4367 (5) | 0.0557 (17) | |
N8 | 0.0619 (3) | 0.7165 (5) | 0.3057 (4) | 0.0503 (17) | |
O1 | −0.2578 (3) | 0.6306 (5) | 0.0585 (4) | 0.0735 (19) | |
O2 | −0.3461 (3) | 0.6239 (4) | −0.1741 (4) | 0.0676 (16) | |
H2A | −0.3156 | 0.6264 | −0.1366 | 0.101* | |
O3 | 0.2871 (3) | 0.6217 (5) | 0.6922 (5) | 0.091 (2) | |
O4 | 0.3802 (3) | 0.6600 (5) | 0.9387 (5) | 0.083 (2) | |
H4 | 0.3502 | 0.6625 | 0.9002 | 0.125* | |
O5 | 0.0976 (4) | 0.6507 (7) | 0.9035 (7) | 0.117 (3) | |
H5A | 0.0871 | 0.5985 | 0.9237 | 0.175* | |
C1 | −0.2012 (4) | 0.6224 (6) | 0.0372 (6) | 0.052 (2) | |
C2 | −0.1235 (4) | 0.6273 (6) | 0.2826 (6) | 0.058 (2) | |
H2B | −0.1371 | 0.6369 | 0.3461 | 0.070* | |
C3 | −0.1693 (4) | 0.6304 (6) | 0.2090 (6) | 0.057 (2) | |
H3 | −0.2124 | 0.6413 | 0.2230 | 0.069* | |
C4 | −0.1489 (3) | 0.6168 (5) | 0.1149 (6) | 0.0421 (18) | |
C5 | −0.0846 (4) | 0.5984 (5) | 0.0988 (6) | 0.050 (2) | |
H5B | −0.0694 | 0.5884 | 0.0362 | 0.060* | |
C6 | −0.0435 (4) | 0.5950 (5) | 0.1764 (6) | 0.0484 (19) | |
H6 | −0.0006 | 0.5804 | 0.1649 | 0.058* | |
C7 | −0.2105 (4) | 0.6256 (6) | −0.2147 (6) | 0.054 (2) | |
H7 | −0.1671 | 0.6253 | −0.2309 | 0.065* | |
C8 | −0.2581 (4) | 0.6271 (6) | −0.2900 (6) | 0.051 (2) | |
C9 | −0.3244 (4) | 0.6246 (6) | −0.2658 (5) | 0.051 (2) | |
C10 | −0.3694 (4) | 0.6209 (5) | −0.3420 (6) | 0.054 (2) | |
C11 | −0.3497 (5) | 0.6219 (6) | −0.4368 (7) | 0.067 (3) | |
H11 | −0.3798 | 0.6195 | −0.4866 | 0.081* | |
C12 | −0.2849 (5) | 0.6264 (6) | −0.4578 (6) | 0.065 (2) | |
C13 | −0.2408 (4) | 0.6280 (6) | −0.3868 (6) | 0.062 (2) | |
H13 | −0.1974 | 0.6297 | −0.4031 | 0.074* | |
C14 | 0.2316 (4) | 0.6278 (6) | 0.7178 (7) | 0.059 (2) | |
C15 | 0.0667 (4) | 0.6362 (6) | 0.5984 (6) | 0.062 (2) | |
H15 | 0.0235 | 0.6397 | 0.6157 | 0.074* | |
C16 | 0.1127 (4) | 0.6387 (7) | 0.6712 (7) | 0.069 (3) | |
H16 | 0.1005 | 0.6465 | 0.7356 | 0.082* | |
C17 | 0.1767 (4) | 0.6297 (6) | 0.6471 (6) | 0.054 (2) | |
C18 | 0.1929 (4) | 0.6216 (6) | 0.5497 (6) | 0.062 (2) | |
H18 | 0.2356 | 0.6160 | 0.5307 | 0.074* | |
C19 | 0.1443 (4) | 0.6221 (6) | 0.4821 (6) | 0.059 (2) | |
H19 | 0.1553 | 0.6174 | 0.4169 | 0.071* | |
C20 | 0.2453 (5) | 0.6247 (6) | 0.9690 (7) | 0.069 (3) | |
H20 | 0.2020 | 0.6160 | 0.9835 | 0.083* | |
C21 | 0.2929 (5) | 0.6265 (6) | 1.0473 (6) | 0.062 (3) | |
C22 | 0.3576 (5) | 0.6424 (6) | 1.0270 (7) | 0.064 (2) | |
C23 | 0.3996 (4) | 0.6434 (6) | 1.1069 (8) | 0.068 (3) | |
C24 | 0.3773 (5) | 0.6304 (6) | 1.2004 (7) | 0.072 (3) | |
H24 | 0.4059 | 0.6305 | 1.2523 | 0.086* | |
C25 | 0.3152 (6) | 0.6180 (6) | 1.2155 (7) | 0.076 (3) | |
C26 | 0.2733 (5) | 0.6152 (6) | 1.1395 (7) | 0.069 (3) | |
H26 | 0.2298 | 0.6051 | 1.1517 | 0.083* | |
C27 | −0.0752 (4) | 0.7704 (7) | 0.5004 (7) | 0.067 (2) | |
H27 | −0.0956 | 0.7193 | 0.5293 | 0.080* | |
C28 | −0.0948 (5) | 0.8606 (7) | 0.5279 (8) | 0.075 (3) | |
H28 | −0.1274 | 0.8693 | 0.5731 | 0.090* | |
C29 | −0.0642 (5) | 0.9364 (9) | 0.4857 (7) | 0.084 (3) | |
H29 | −0.0766 | 0.9976 | 0.5014 | 0.101* | |
C30 | −0.0152 (4) | 0.9214 (7) | 0.4199 (6) | 0.062 (2) | |
C31 | 0.0011 (4) | 0.8272 (5) | 0.3967 (7) | 0.0502 (17) | |
C32 | 0.0493 (4) | 0.8083 (6) | 0.3272 (6) | 0.051 (2) | |
C33 | 0.0833 (5) | 0.8831 (6) | 0.2830 (6) | 0.058 (2) | |
C34 | 0.1290 (4) | 0.8613 (7) | 0.2135 (7) | 0.065 (3) | |
H34 | 0.1528 | 0.9089 | 0.1839 | 0.078* | |
C35 | 0.1386 (4) | 0.7700 (8) | 0.1893 (7) | 0.072 (3) | |
H35 | 0.1679 | 0.7542 | 0.1410 | 0.087* | |
C36 | 0.1037 (4) | 0.6990 (7) | 0.2380 (6) | 0.068 (2) | |
H36 | 0.1110 | 0.6364 | 0.2207 | 0.082* | |
C37 | 0.0213 (5) | 0.9959 (7) | 0.3775 (8) | 0.077 (3) | |
H37 | 0.0130 | 1.0580 | 0.3955 | 0.092* | |
C38 | 0.0686 (5) | 0.9776 (7) | 0.3105 (8) | 0.085 (3) | |
H38 | 0.0912 | 1.0275 | 0.2828 | 0.102* | |
C39 | 0.0539 (9) | 0.7183 (13) | 0.9363 (15) | 0.190 (8) | |
H39A | 0.0433 | 0.7058 | 1.0028 | 0.286* | |
H39B | 0.0156 | 0.7155 | 0.8976 | 0.286* | |
H39C | 0.0727 | 0.7799 | 0.9310 | 0.286* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.0473 (6) | 0.0645 (6) | 0.0411 (5) | 0.0011 (5) | −0.0037 (5) | 0.0018 (6) |
Cl1 | 0.0679 (14) | 0.0748 (14) | 0.0607 (13) | 0.0178 (11) | −0.0068 (11) | −0.0051 (12) |
Cl2 | 0.0650 (14) | 0.0895 (17) | 0.0516 (13) | −0.0075 (12) | 0.0000 (11) | 0.0098 (12) |
Cl3 | 0.0489 (14) | 0.148 (3) | 0.091 (2) | −0.0081 (15) | −0.0042 (14) | 0.0209 (19) |
Cl4 | 0.090 (2) | 0.179 (3) | 0.0411 (15) | 0.0049 (18) | −0.0026 (12) | 0.0099 (17) |
Cl5 | 0.0721 (19) | 0.146 (3) | 0.109 (2) | 0.0119 (18) | −0.0259 (17) | −0.036 (2) |
Cl6 | 0.146 (3) | 0.131 (3) | 0.0541 (16) | 0.0219 (19) | −0.0119 (18) | 0.0011 (18) |
N1 | 0.040 (4) | 0.059 (4) | 0.039 (4) | 0.008 (3) | −0.004 (3) | −0.003 (3) |
N2 | 0.043 (4) | 0.084 (5) | 0.040 (4) | 0.005 (3) | −0.012 (3) | 0.002 (4) |
N3 | 0.049 (4) | 0.073 (4) | 0.035 (4) | 0.006 (3) | −0.008 (3) | −0.003 (3) |
N4 | 0.055 (4) | 0.062 (4) | 0.042 (4) | 0.011 (3) | 0.000 (3) | −0.007 (3) |
N5 | 0.061 (5) | 0.092 (5) | 0.044 (5) | 0.005 (4) | −0.013 (4) | −0.005 (4) |
N6 | 0.068 (5) | 0.071 (5) | 0.046 (5) | 0.014 (3) | −0.020 (4) | −0.003 (4) |
N7 | 0.042 (4) | 0.086 (5) | 0.039 (4) | 0.003 (4) | 0.001 (3) | −0.008 (4) |
N8 | 0.041 (4) | 0.070 (5) | 0.039 (4) | 0.008 (3) | −0.005 (3) | 0.000 (3) |
O1 | 0.050 (4) | 0.116 (6) | 0.055 (4) | 0.016 (4) | −0.002 (3) | −0.015 (4) |
O2 | 0.048 (3) | 0.106 (5) | 0.049 (4) | 0.006 (3) | −0.002 (3) | 0.006 (3) |
O3 | 0.049 (4) | 0.166 (7) | 0.056 (4) | 0.010 (4) | −0.015 (3) | −0.018 (4) |
O4 | 0.069 (4) | 0.110 (5) | 0.070 (5) | 0.019 (4) | −0.010 (4) | −0.010 (4) |
O5 | 0.083 (5) | 0.166 (8) | 0.102 (6) | −0.027 (5) | 0.005 (5) | 0.039 (6) |
C1 | 0.050 (5) | 0.059 (5) | 0.046 (5) | 0.011 (4) | −0.007 (4) | −0.013 (4) |
C2 | 0.058 (5) | 0.086 (6) | 0.031 (4) | 0.015 (5) | 0.009 (4) | 0.001 (4) |
C3 | 0.043 (5) | 0.088 (6) | 0.041 (5) | 0.012 (4) | 0.002 (4) | −0.017 (4) |
C4 | 0.036 (4) | 0.046 (4) | 0.044 (4) | 0.007 (3) | −0.006 (4) | −0.011 (4) |
C5 | 0.050 (5) | 0.059 (5) | 0.041 (5) | 0.004 (4) | −0.001 (4) | −0.001 (4) |
C6 | 0.042 (4) | 0.061 (5) | 0.042 (5) | 0.001 (4) | 0.000 (4) | 0.001 (4) |
C7 | 0.052 (5) | 0.074 (6) | 0.036 (5) | 0.005 (4) | −0.014 (4) | 0.001 (4) |
C8 | 0.051 (5) | 0.063 (6) | 0.038 (5) | 0.006 (4) | −0.003 (4) | 0.002 (4) |
C9 | 0.046 (5) | 0.071 (6) | 0.036 (5) | −0.001 (4) | −0.005 (4) | 0.005 (4) |
C10 | 0.041 (4) | 0.063 (5) | 0.057 (6) | −0.003 (4) | −0.012 (4) | 0.010 (5) |
C11 | 0.061 (6) | 0.099 (8) | 0.042 (5) | −0.009 (5) | −0.016 (5) | 0.001 (5) |
C12 | 0.072 (7) | 0.090 (7) | 0.034 (5) | −0.010 (5) | −0.007 (4) | 0.009 (4) |
C13 | 0.055 (5) | 0.090 (7) | 0.041 (5) | 0.015 (5) | −0.008 (4) | −0.003 (5) |
C14 | 0.052 (6) | 0.073 (6) | 0.052 (6) | 0.002 (5) | −0.017 (4) | 0.000 (4) |
C15 | 0.047 (5) | 0.096 (7) | 0.042 (5) | 0.005 (5) | −0.009 (4) | 0.000 (5) |
C16 | 0.065 (6) | 0.106 (7) | 0.034 (5) | 0.001 (5) | −0.011 (5) | −0.006 (5) |
C17 | 0.046 (5) | 0.064 (5) | 0.051 (5) | 0.003 (4) | −0.009 (4) | −0.010 (4) |
C18 | 0.045 (5) | 0.102 (7) | 0.037 (5) | 0.000 (5) | −0.009 (4) | −0.006 (5) |
C19 | 0.050 (5) | 0.089 (6) | 0.039 (5) | −0.009 (5) | −0.009 (4) | 0.000 (4) |
C20 | 0.067 (6) | 0.083 (7) | 0.058 (6) | 0.013 (5) | −0.016 (5) | −0.006 (5) |
C21 | 0.083 (8) | 0.055 (5) | 0.048 (6) | 0.015 (5) | −0.024 (5) | −0.010 (4) |
C22 | 0.054 (6) | 0.079 (6) | 0.059 (6) | 0.012 (5) | −0.008 (5) | −0.015 (5) |
C23 | 0.053 (6) | 0.070 (6) | 0.080 (7) | 0.012 (5) | −0.017 (5) | −0.018 (5) |
C24 | 0.085 (8) | 0.076 (7) | 0.056 (6) | 0.016 (6) | −0.023 (5) | −0.018 (5) |
C25 | 0.092 (8) | 0.071 (7) | 0.065 (7) | 0.022 (6) | −0.015 (6) | −0.003 (5) |
C26 | 0.086 (7) | 0.064 (6) | 0.057 (6) | 0.020 (5) | −0.020 (5) | −0.010 (5) |
C27 | 0.062 (6) | 0.080 (7) | 0.059 (6) | −0.007 (5) | −0.007 (5) | −0.004 (5) |
C28 | 0.046 (6) | 0.087 (8) | 0.092 (8) | 0.012 (5) | 0.005 (5) | −0.022 (7) |
C29 | 0.083 (7) | 0.103 (9) | 0.066 (7) | 0.047 (7) | −0.018 (6) | −0.034 (6) |
C30 | 0.054 (5) | 0.075 (6) | 0.057 (6) | 0.011 (5) | −0.018 (4) | −0.010 (5) |
C31 | 0.043 (4) | 0.064 (5) | 0.044 (4) | −0.002 (4) | −0.009 (4) | −0.008 (5) |
C32 | 0.045 (5) | 0.067 (5) | 0.040 (5) | −0.002 (4) | −0.013 (4) | −0.001 (4) |
C33 | 0.070 (6) | 0.062 (6) | 0.043 (5) | −0.006 (5) | −0.018 (4) | 0.003 (4) |
C34 | 0.054 (6) | 0.077 (7) | 0.064 (6) | −0.003 (5) | 0.006 (5) | 0.022 (5) |
C35 | 0.053 (5) | 0.099 (8) | 0.064 (6) | 0.000 (5) | 0.007 (5) | 0.017 (6) |
C36 | 0.069 (6) | 0.081 (7) | 0.055 (6) | 0.003 (5) | 0.003 (5) | −0.002 (5) |
C37 | 0.093 (7) | 0.059 (5) | 0.079 (7) | −0.001 (5) | −0.013 (6) | −0.004 (5) |
C38 | 0.106 (9) | 0.069 (7) | 0.081 (8) | 0.000 (6) | −0.018 (7) | 0.002 (6) |
C39 | 0.155 (17) | 0.21 (2) | 0.201 (19) | −0.031 (14) | 0.026 (15) | 0.014 (17) |
Co1—N8 | 2.170 (7) | C10—C11 | 1.370 (12) |
Co1—N7 | 2.170 (7) | C11—C12 | 1.382 (13) |
Co1—N1 | 2.217 (6) | C11—H11 | 0.9300 |
Co1—N4 | 2.235 (7) | C12—C13 | 1.343 (12) |
Co1—Cl1 | 2.401 (2) | C13—H13 | 0.9300 |
Co1—Cl2 | 2.419 (2) | C14—C17 | 1.501 (11) |
Cl3—C10 | 1.704 (8) | C15—C16 | 1.389 (11) |
Cl4—C12 | 1.740 (9) | C15—H15 | 0.9300 |
Cl5—C23 | 1.721 (10) | C16—C17 | 1.378 (11) |
Cl6—C25 | 1.736 (11) | C16—H16 | 0.9300 |
N1—C2 | 1.321 (9) | C17—C18 | 1.390 (11) |
N1—C6 | 1.325 (10) | C18—C19 | 1.376 (11) |
N2—C1 | 1.359 (10) | C18—H18 | 0.9300 |
N2—N3 | 1.368 (8) | C19—H19 | 0.9300 |
N2—H2 | 0.8600 | C20—C21 | 1.465 (12) |
N3—C7 | 1.273 (10) | C20—H20 | 0.9300 |
N4—C15 | 1.327 (10) | C21—C26 | 1.345 (13) |
N4—C19 | 1.344 (10) | C21—C22 | 1.393 (13) |
N5—C14 | 1.351 (11) | C22—C23 | 1.407 (12) |
N5—N6 | 1.389 (9) | C23—C24 | 1.383 (14) |
N5—H5 | 0.8600 | C24—C25 | 1.321 (14) |
N6—C20 | 1.293 (11) | C24—H24 | 0.9300 |
N7—C27 | 1.309 (11) | C25—C26 | 1.365 (13) |
N7—C31 | 1.358 (10) | C26—H26 | 0.9300 |
N8—C36 | 1.301 (10) | C27—C28 | 1.393 (12) |
N8—C32 | 1.360 (10) | C27—H27 | 0.9300 |
O1—C1 | 1.220 (9) | C28—C29 | 1.377 (14) |
O2—C9 | 1.344 (9) | C28—H28 | 0.9300 |
O2—H2A | 0.8200 | C29—C30 | 1.382 (12) |
O3—C14 | 1.209 (10) | C29—H29 | 0.9300 |
O4—C22 | 1.329 (11) | C30—C31 | 1.413 (11) |
O4—H4 | 0.8200 | C30—C37 | 1.426 (12) |
O5—C39 | 1.396 (18) | C31—C32 | 1.412 (11) |
O5—H5A | 0.8200 | C32—C33 | 1.412 (11) |
C1—C4 | 1.528 (11) | C33—C34 | 1.386 (12) |
C2—C3 | 1.392 (11) | C33—C38 | 1.424 (12) |
C2—H2B | 0.9300 | C34—C35 | 1.350 (12) |
C3—C4 | 1.378 (10) | C34—H34 | 0.9300 |
C3—H3 | 0.9300 | C35—C36 | 1.411 (12) |
C4—C5 | 1.382 (10) | C35—H35 | 0.9300 |
C5—C6 | 1.370 (10) | C36—H36 | 0.9300 |
C5—H5B | 0.9300 | C37—C38 | 1.374 (14) |
C6—H6 | 0.9300 | C37—H37 | 0.9300 |
C7—C8 | 1.435 (11) | C38—H38 | 0.9300 |
C7—H7 | 0.9300 | C39—H39A | 0.9600 |
C8—C13 | 1.383 (11) | C39—H39B | 0.9600 |
C8—C9 | 1.418 (11) | C39—H39C | 0.9600 |
C9—C10 | 1.408 (11) | ||
N8—Co1—N7 | 76.3 (3) | N5—C14—C17 | 114.5 (8) |
N8—Co1—N1 | 87.0 (2) | N4—C15—C16 | 122.7 (8) |
N7—Co1—N1 | 91.8 (2) | N4—C15—H15 | 118.6 |
N8—Co1—N4 | 87.5 (2) | C16—C15—H15 | 118.6 |
N7—Co1—N4 | 88.0 (2) | C17—C16—C15 | 119.3 (8) |
N1—Co1—N4 | 174.4 (3) | C17—C16—H16 | 120.3 |
N8—Co1—Cl1 | 95.86 (19) | C15—C16—H16 | 120.3 |
N7—Co1—Cl1 | 171.9 (2) | C16—C17—C18 | 118.3 (7) |
N1—Co1—Cl1 | 90.04 (17) | C16—C17—C14 | 125.4 (8) |
N4—Co1—Cl1 | 89.40 (17) | C18—C17—C14 | 116.3 (8) |
N8—Co1—Cl2 | 166.75 (19) | C19—C18—C17 | 118.5 (8) |
N7—Co1—Cl2 | 90.4 (2) | C19—C18—H18 | 120.7 |
N1—Co1—Cl2 | 93.95 (18) | C17—C18—H18 | 120.7 |
N4—Co1—Cl2 | 91.69 (19) | N4—C19—C18 | 123.5 (8) |
Cl1—Co1—Cl2 | 97.36 (9) | N4—C19—H19 | 118.3 |
C2—N1—C6 | 117.5 (7) | C18—C19—H19 | 118.3 |
C2—N1—Co1 | 119.3 (5) | N6—C20—C21 | 120.4 (9) |
C6—N1—Co1 | 123.1 (5) | N6—C20—H20 | 119.8 |
C1—N2—N3 | 116.1 (7) | C21—C20—H20 | 119.8 |
C1—N2—H2 | 122.0 | C26—C21—C22 | 120.1 (9) |
N3—N2—H2 | 122.0 | C26—C21—C20 | 119.3 (10) |
C7—N3—N2 | 118.9 (7) | C22—C21—C20 | 120.5 (9) |
C15—N4—C19 | 117.6 (7) | O4—C22—C21 | 123.8 (8) |
C15—N4—Co1 | 121.9 (5) | O4—C22—C23 | 119.7 (9) |
C19—N4—Co1 | 120.3 (5) | C21—C22—C23 | 116.4 (9) |
C14—N5—N6 | 116.5 (7) | C24—C23—C22 | 121.4 (9) |
C14—N5—H5 | 121.7 | C24—C23—Cl5 | 120.1 (8) |
N6—N5—H5 | 121.7 | C22—C23—Cl5 | 118.5 (8) |
C20—N6—N5 | 115.2 (8) | C25—C24—C23 | 119.5 (9) |
C27—N7—C31 | 117.8 (8) | C25—C24—H24 | 120.2 |
C27—N7—Co1 | 128.3 (6) | C23—C24—H24 | 120.2 |
C31—N7—Co1 | 113.8 (5) | C24—C25—C26 | 120.5 (11) |
C36—N8—C32 | 117.9 (7) | C24—C25—Cl6 | 119.0 (8) |
C36—N8—Co1 | 128.2 (6) | C26—C25—Cl6 | 120.5 (9) |
C32—N8—Co1 | 113.9 (5) | C21—C26—C25 | 122.0 (11) |
C9—O2—H2A | 109.5 | C21—C26—H26 | 119.0 |
C22—O4—H4 | 109.5 | C25—C26—H26 | 119.0 |
C39—O5—H5A | 109.5 | N7—C27—C28 | 124.7 (9) |
O1—C1—N2 | 122.5 (7) | N7—C27—H27 | 117.7 |
O1—C1—C4 | 121.5 (7) | C28—C27—H27 | 117.7 |
N2—C1—C4 | 116.0 (7) | C29—C28—C27 | 117.7 (9) |
N1—C2—C3 | 123.4 (8) | C29—C28—H28 | 121.2 |
N1—C2—H2B | 118.3 | C27—C28—H28 | 121.2 |
C3—C2—H2B | 118.3 | C28—C29—C30 | 119.9 (9) |
C4—C3—C2 | 118.2 (7) | C28—C29—H29 | 120.0 |
C4—C3—H3 | 120.9 | C30—C29—H29 | 120.0 |
C2—C3—H3 | 120.9 | C29—C30—C31 | 118.1 (9) |
C3—C4—C5 | 118.4 (7) | C29—C30—C37 | 123.3 (10) |
C3—C4—C1 | 115.8 (7) | C31—C30—C37 | 118.5 (8) |
C5—C4—C1 | 125.8 (7) | N7—C31—C32 | 118.0 (7) |
C6—C5—C4 | 119.0 (7) | N7—C31—C30 | 121.8 (8) |
C6—C5—H5B | 120.5 | C32—C31—C30 | 120.2 (8) |
C4—C5—H5B | 120.5 | N8—C32—C31 | 117.7 (7) |
N1—C6—C5 | 123.5 (7) | N8—C32—C33 | 121.8 (8) |
N1—C6—H6 | 118.3 | C31—C32—C33 | 120.4 (8) |
C5—C6—H6 | 118.3 | C34—C33—C32 | 118.4 (9) |
N3—C7—C8 | 120.6 (8) | C34—C33—C38 | 122.8 (9) |
N3—C7—H7 | 119.7 | C32—C33—C38 | 118.9 (9) |
C8—C7—H7 | 119.7 | C35—C34—C33 | 119.1 (9) |
C13—C8—C9 | 118.8 (7) | C35—C34—H34 | 120.5 |
C13—C8—C7 | 121.2 (8) | C33—C34—H34 | 120.5 |
C9—C8—C7 | 120.0 (7) | C34—C35—C36 | 119.3 (9) |
O2—C9—C10 | 118.6 (7) | C34—C35—H35 | 120.3 |
O2—C9—C8 | 123.3 (7) | C36—C35—H35 | 120.3 |
C10—C9—C8 | 118.1 (7) | N8—C36—C35 | 123.4 (9) |
C11—C10—C9 | 120.9 (8) | N8—C36—H36 | 118.3 |
C11—C10—Cl3 | 119.3 (7) | C35—C36—H36 | 118.3 |
C9—C10—Cl3 | 119.8 (7) | C38—C37—C30 | 121.2 (9) |
C10—C11—C12 | 119.5 (8) | C38—C37—H37 | 119.4 |
C10—C11—H11 | 120.3 | C30—C37—H37 | 119.4 |
C12—C11—H11 | 120.3 | C37—C38—C33 | 120.6 (10) |
C13—C12—C11 | 121.0 (8) | C37—C38—H38 | 119.7 |
C13—C12—Cl4 | 121.7 (8) | C33—C38—H38 | 119.7 |
C11—C12—Cl4 | 117.4 (7) | O5—C39—H39A | 109.5 |
C12—C13—C8 | 121.7 (8) | O5—C39—H39B | 109.5 |
C12—C13—H13 | 119.1 | H39A—C39—H39B | 109.5 |
C8—C13—H13 | 119.1 | O5—C39—H39C | 109.5 |
O3—C14—N5 | 123.0 (8) | H39A—C39—H39C | 109.5 |
O3—C14—C17 | 122.4 (8) | H39B—C39—H39C | 109.5 |
N8—Co1—N1—C2 | −126.7 (6) | C9—C8—C13—C12 | −0.1 (14) |
N7—Co1—N1—C2 | −50.5 (6) | C7—C8—C13—C12 | 177.8 (8) |
N4—Co1—N1—C2 | −138 (2) | N6—N5—C14—O3 | 4.1 (14) |
Cl1—Co1—N1—C2 | 137.5 (6) | N6—N5—C14—C17 | −177.0 (7) |
Cl2—Co1—N1—C2 | 40.1 (6) | C19—N4—C15—C16 | 1.3 (13) |
N8—Co1—N1—C6 | 51.9 (6) | Co1—N4—C15—C16 | 176.3 (7) |
N7—Co1—N1—C6 | 128.1 (6) | N4—C15—C16—C17 | −2.7 (14) |
N4—Co1—N1—C6 | 40 (3) | C15—C16—C17—C18 | 2.2 (13) |
Cl1—Co1—N1—C6 | −43.9 (6) | C15—C16—C17—C14 | −177.8 (8) |
Cl2—Co1—N1—C6 | −141.3 (6) | O3—C14—C17—C16 | −178.4 (9) |
C1—N2—N3—C7 | 178.4 (7) | N5—C14—C17—C16 | 2.6 (13) |
N8—Co1—N4—C15 | 136.9 (7) | O3—C14—C17—C18 | 1.6 (13) |
N7—Co1—N4—C15 | 60.5 (7) | N5—C14—C17—C18 | −177.4 (8) |
N1—Co1—N4—C15 | 148 (2) | C16—C17—C18—C19 | −0.6 (13) |
Cl1—Co1—N4—C15 | −127.2 (6) | C14—C17—C18—C19 | 179.4 (8) |
Cl2—Co1—N4—C15 | −29.9 (6) | C15—N4—C19—C18 | 0.4 (13) |
N8—Co1—N4—C19 | −48.3 (6) | Co1—N4—C19—C18 | −174.7 (7) |
N7—Co1—N4—C19 | −124.7 (6) | C17—C18—C19—N4 | −0.7 (14) |
N1—Co1—N4—C19 | −37 (3) | N5—N6—C20—C21 | 179.9 (7) |
Cl1—Co1—N4—C19 | 47.6 (6) | N6—C20—C21—C26 | −179.7 (9) |
Cl2—Co1—N4—C19 | 145.0 (6) | N6—C20—C21—C22 | 2.0 (13) |
C14—N5—N6—C20 | −170.0 (8) | C26—C21—C22—O4 | −175.7 (9) |
N8—Co1—N7—C27 | 179.8 (8) | C20—C21—C22—O4 | 2.5 (14) |
N1—Co1—N7—C27 | 93.3 (7) | C26—C21—C22—C23 | 1.5 (13) |
N4—Co1—N7—C27 | −92.3 (7) | C20—C21—C22—C23 | 179.7 (8) |
Cl1—Co1—N7—C27 | −164.0 (10) | O4—C22—C23—C24 | 176.4 (9) |
Cl2—Co1—N7—C27 | −0.6 (7) | C21—C22—C23—C24 | −0.8 (13) |
N8—Co1—N7—C31 | −3.9 (5) | O4—C22—C23—Cl5 | −4.0 (12) |
N1—Co1—N7—C31 | −90.4 (5) | C21—C22—C23—Cl5 | 178.8 (6) |
N4—Co1—N7—C31 | 84.0 (6) | C22—C23—C24—C25 | −0.8 (14) |
Cl1—Co1—N7—C31 | 12.3 (17) | Cl5—C23—C24—C25 | 179.6 (7) |
Cl2—Co1—N7—C31 | 175.6 (5) | C23—C24—C25—C26 | 1.9 (15) |
N7—Co1—N8—C36 | −175.4 (7) | C23—C24—C25—Cl6 | −176.6 (7) |
N1—Co1—N8—C36 | −82.8 (7) | C22—C21—C26—C25 | −0.5 (13) |
N4—Co1—N8—C36 | 96.1 (7) | C20—C21—C26—C25 | −178.7 (8) |
Cl1—Co1—N8—C36 | 6.9 (7) | C24—C25—C26—C21 | −1.2 (14) |
Cl2—Co1—N8—C36 | −177.2 (6) | Cl6—C25—C26—C21 | 177.2 (7) |
N7—Co1—N8—C32 | 3.5 (5) | C31—N7—C27—C28 | 2.1 (13) |
N1—Co1—N8—C32 | 96.0 (5) | Co1—N7—C27—C28 | 178.3 (7) |
N4—Co1—N8—C32 | −85.1 (5) | N7—C27—C28—C29 | −0.6 (15) |
Cl1—Co1—N8—C32 | −174.2 (5) | C27—C28—C29—C30 | −1.2 (14) |
Cl2—Co1—N8—C32 | 1.6 (11) | C28—C29—C30—C31 | 1.3 (13) |
N3—N2—C1—O1 | −3.2 (11) | C28—C29—C30—C37 | −176.2 (9) |
N3—N2—C1—C4 | 179.1 (6) | C27—N7—C31—C32 | −179.4 (7) |
C6—N1—C2—C3 | −2.0 (12) | Co1—N7—C31—C32 | 3.9 (9) |
Co1—N1—C2—C3 | 176.7 (7) | C27—N7—C31—C30 | −2.0 (12) |
N1—C2—C3—C4 | −0.5 (14) | Co1—N7—C31—C30 | −178.7 (6) |
C2—C3—C4—C5 | 1.7 (13) | C29—C30—C31—N7 | 0.3 (12) |
C2—C3—C4—C1 | −179.2 (7) | C37—C30—C31—N7 | 177.9 (8) |
O1—C1—C4—C3 | −5.7 (12) | C29—C30—C31—C32 | 177.6 (7) |
N2—C1—C4—C3 | 172.0 (8) | C37—C30—C31—C32 | −4.8 (12) |
O1—C1—C4—C5 | 173.3 (8) | C36—N8—C32—C31 | 176.3 (7) |
N2—C1—C4—C5 | −9.0 (11) | Co1—N8—C32—C31 | −2.7 (9) |
C3—C4—C5—C6 | −0.5 (12) | C36—N8—C32—C33 | −4.4 (11) |
C1—C4—C5—C6 | −179.5 (7) | Co1—N8—C32—C33 | 176.6 (6) |
C2—N1—C6—C5 | 3.4 (12) | N7—C31—C32—N8 | −0.9 (11) |
Co1—N1—C6—C5 | −175.3 (6) | C30—C31—C32—N8 | −178.3 (7) |
C4—C5—C6—N1 | −2.1 (12) | N7—C31—C32—C33 | 179.8 (7) |
N2—N3—C7—C8 | 178.5 (7) | C30—C31—C32—C33 | 2.4 (12) |
N3—C7—C8—C13 | −179.8 (9) | N8—C32—C33—C34 | 2.3 (12) |
N3—C7—C8—C9 | −1.9 (12) | C31—C32—C33—C34 | −178.4 (8) |
C13—C8—C9—O2 | −179.8 (8) | N8—C32—C33—C38 | −178.6 (8) |
C7—C8—C9—O2 | 2.3 (12) | C31—C32—C33—C38 | 0.7 (12) |
C13—C8—C9—C10 | 1.5 (12) | C32—C33—C34—C35 | 1.2 (13) |
C7—C8—C9—C10 | −176.5 (7) | C38—C33—C34—C35 | −177.8 (9) |
O2—C9—C10—C11 | 179.7 (8) | C33—C34—C35—C36 | −2.5 (14) |
C8—C9—C10—C11 | −1.5 (12) | C32—N8—C36—C35 | 3.1 (12) |
O2—C9—C10—Cl3 | 0.1 (11) | Co1—N8—C36—C35 | −178.1 (6) |
C8—C9—C10—Cl3 | 178.9 (6) | C34—C35—C36—N8 | 0.3 (14) |
C9—C10—C11—C12 | 0.2 (13) | C29—C30—C37—C38 | −178.3 (9) |
Cl3—C10—C11—C12 | 179.7 (7) | C31—C30—C37—C38 | 4.3 (14) |
C10—C11—C12—C13 | 1.3 (14) | C30—C37—C38—C33 | −1.3 (15) |
C10—C11—C12—Cl4 | −178.3 (7) | C34—C33—C38—C37 | 177.8 (9) |
C11—C12—C13—C8 | −1.3 (15) | C32—C33—C38—C37 | −1.2 (14) |
Cl4—C12—C13—C8 | 178.3 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···Cl1i | 0.86 | 2.56 | 3.280 (7) | 142 |
N5—H5···O5 | 0.86 | 1.91 | 2.739 (11) | 162 |
O2—H2A···N3 | 0.82 | 1.85 | 2.562 (8) | 145 |
O4—H4···N6 | 0.82 | 1.88 | 2.592 (9) | 145 |
O5—H5A···Cl2ii | 0.82 | 2.24 | 3.052 (9) | 171 |
Symmetry codes: (i) −x, −y+1, z−1/2; (ii) −x, −y+1, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [CoCl2(C13H9Cl2N3O2)2(C12H8N2)]·CH4O |
Mr | 962.34 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 298 |
a, b, c (Å) | 20.797 (3), 14.1641 (16), 13.7952 (10) |
V (Å3) | 4063.7 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.87 |
Crystal size (mm) | 0.32 × 0.23 × 0.22 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.768, 0.831 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17533, 7003, 3870 |
Rint | 0.052 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.170, 1.03 |
No. of reflections | 7003 |
No. of parameters | 532 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.51, −0.57 |
Absolute structure | Flack (1983), 3259 Friedel pairs |
Absolute structure parameter | 0.50 (3) |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Co1—N8 | 2.170 (7) | Co1—Cl1 | 2.401 (2) |
Co1—N7 | 2.170 (7) | Co1—Cl2 | 2.419 (2) |
Co1—N1 | 2.217 (6) | N2—N3 | 1.368 (8) |
Co1—N4 | 2.235 (7) | N5—N6 | 1.389 (9) |
N8—Co1—N7 | 76.3 (3) | N1—Co1—Cl1 | 90.04 (17) |
N8—Co1—N1 | 87.0 (2) | N4—Co1—Cl1 | 89.40 (17) |
N7—Co1—N1 | 91.8 (2) | N8—Co1—Cl2 | 166.75 (19) |
N8—Co1—N4 | 87.5 (2) | N7—Co1—Cl2 | 90.4 (2) |
N7—Co1—N4 | 88.0 (2) | N1—Co1—Cl2 | 93.95 (18) |
N1—Co1—N4 | 174.4 (3) | N4—Co1—Cl2 | 91.69 (19) |
N8—Co1—Cl1 | 95.86 (19) | Cl1—Co1—Cl2 | 97.36 (9) |
N7—Co1—Cl1 | 171.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···Cl1i | 0.86 | 2.56 | 3.280 (7) | 142.1 |
N5—H5···O5 | 0.86 | 1.91 | 2.739 (11) | 161.6 |
O2—H2A···N3 | 0.82 | 1.85 | 2.562 (8) | 145.3 |
O4—H4···N6 | 0.82 | 1.88 | 2.592 (9) | 145.4 |
O5—H5A···Cl2ii | 0.82 | 2.24 | 3.052 (9) | 170.9 |
Symmetry codes: (i) −x, −y+1, z−1/2; (ii) −x, −y+1, z+1/2. |
Acknowledgements
We acknowledge financial support by the Key Laboratory of Non-Ferrous Metal Materials and New Processing Technology, Ministry of Education, China.
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In the field of coordination chemistry, continuing interest in the acylhydrazones transition metal complexes stems from their analytical, catalytic chemistry and as models for metalloenzymes. Acylhydrazone ligands can act as bidentate, tridentate or tetradentate ligands depending on the nature of heterocyclic ring substituents attached to the hydrazone unit.
In (I), there is methanol solvate molecule, and the CoII atom is coordinated by two N atoms from pyridyls of H2L and two N atoms from 1,10-phenanthroline and two Cl ions, which form a slightly distorted tetragonal-dipyramid geometry (Fig. 1). From the bond lengths of (I), we can find the N atoms from 1,10-phenanthroline possess stronger coordinating capability compared to the pyridyls. The acylhydrazone of (I) is a kind of polydentate ligand which contains three heteroatoms. However, the acylhydrazone groups are not involved in the coordination. On the other hand, this phenomenon illustrates the pyridyl N atom of H2L has a stronger coordinating capability than the acylhydrazone group. Also in the structure of 2-pyridinecarbaldehyde isonicotinoylhydrazone and manganese chloride at 2:1 mole ratio no coordination of the acylhydrazone groups with the metal ion was observed (Armstrong et al., 2003). The three-dimensional network through N–H···Cl, N–H···O, O–H···N, O–H···N and O–H···Cl hydrogen bonds in the packing of (I) is shown in Figure 2.