metal-organic compounds
Aquachlorido{6,6′-dimethoxy-2,2′-[ethane-1,2-diylbis(nitrilomethanylylidene)]diphenolato-κ2O1,N,N′,O1′}cobalt(III) dimethylformamide monosolvate
aCollege of Chemistry and Chemical Engineering, Key Laboratory of Eco-Environment-Related Polymer Materials of the Ministry of Education, Key Laboratory of Polymer Materials of Gansu Province, Key Laboratory of Bioelectrochemistry and Environmental Analysis of Gansu, Northwest Normal University, Lanzhou 730070, People's Republic of China
*Correspondence e-mail: jcliu8@nwnu.edu.cn
In the title compound, [Co(C18H18N2O4)Cl(H2O)]·C3H7NO, the CoIII ion is six-coordinated by a tetradentate 6,6′-dimethoxy-2,2′-[ethane-1,2-diylbis(nitrilomethanylylidene)]diphenolate ligand, with a chloride ion and an aqua ligand in the apical positions. The compound crystallized as a dimethylformamide (DMF) monosolvate. In the crystal, complex molecules are linked via O—Hwater⋯O hydrogen bonds to form a dimer-like arrangement. These dimers are linked via a C—H⋯Cl interaction, and the DMF molecule is linked to the complex molecule by C—H⋯O interactions.
Related literature
For related literature on metal complexes of et al. (1994); Hulme et al. (1997); Li et al. (2008); Wang et al. (1979); Xing (2009). For transition metal complexes of derived from o-vanillin, with antibacterial activity, see: Liu et al. (1990); Viswanathamurthi et al. (2000); Yeap et al. (2003). For the of the ligand, see: Xia et al. (2006). For the of the monohydrate form of the title complex, see: Xing (2009).
see: AurangzebExperimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2008); cell SAINT (Bruker, 2008); 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/S1600536812011324/su2386sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812011324/su2386Isup2.hkl
A colourless solution of 6,6'-dimethoxy-2,2'-[ethane-1,2-diylbis(nitrilomethanylylidene)]diphenol (54.5 mg,0.2 mmol) in DMF (3 ml) was slowly added to a solution of CoCl2 (64 mg, 0.2 mmol) in CH3CN(15 ml), forming a dark red solution that was stirred for 30 min at room temperature. Slow evaporation of the solvent at room temperature gave red block-like crystals of the title compound, suitable for X-ray analysis. The crystals were collected by filtration, washed with cold acetonitrile, and dried under vacuum (yield 77%).
The water H atoms were located in an difference electron-density map and allowed to ride on the O atom with O-H = 0.96 Å. The C-bound H-atoms were included in calculated positions and treated as riding atoms: C-H = 0.93, 0.97 and 0.96 Å for CH, CH2, and CH3 H-atoms, respectively, with Uiso(H) = k × Ueq(O,C), where k = 1.5 for OH and CH3 H-atoms, and k = 1.2 for other H-atoms.
Polydentate Schiff base ligands and their metal complexes have been studied for decades (Aurangzeb et al., 1994, Hulme et al., 1997; Li et al., 2008; Wang et al., 1979; Xing, 2009). Transition metal complexes of
derived from o-vanillin have attracted more attention during past years due to their antibacterial activity (Liu et al., 1990; Viswanathamurthi et al., 2000; Yeap et al., 2003). Herein, we report on the synthesis and of the title cobalt(III) complex.The molecular structure of the title compound is illustrated in Fig. 1. The CoIII ion is coordinated to two N and two O atoms of the tetradentate 6,6'-dimethoxy-2,2'-[ethane-1,2-diylbis(nitrilomethanylylidene)]diphenolate ligand, a Cl- ion and one water molecule. The compound crystallized with a molecule of dimethylformamide, used as solvent. The
of the ligand has been reported previously (Xia et al., 2006), as has the monohydrate form of the title complex (Xing, 2009). The Cl5—Co1—O5 bond angle is 178.77 (7)° suggesting that the CoIII ion has a slightly distorted octahedral environment, with atoms N1, N2, O1 and O2 occupying the equatorial positions, while atoms Cl5 and O5water occupy the axial positions.In the crystal, complex molecules are linked via O-Hwater···O hydrogen bonds to form a dimer-like arrangement. These dimers are linked via a C-H···Cl interaction, and the DMF molecule is linked to the complex molecule by C-H···O interactions (Table 1).
For related literature on metal complexes of
see: Aurangzeb et al. (1994); Hulme et al. (1997); Li et al. (2008); Wang et al. (1979); Xing (2009). For transition metal complexes of derived from o-vanillin, with antibacterial activity, see: Liu et al. (1990); Viswanathamurthi et al. (2000); Yeap et al. (2003). For the of the ligand, see: Xia et al. (2006). For the of the monohydrate form of the title complex, see: Xing (2009).Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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).Fig. 1. A view of the molecular structure of the title complex, with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. |
[Co(C18H18N2O4)Cl(H2O)]·C3H7NO | F(000) = 1064 |
Mr = 511.84 | Dx = 1.478 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2594 reflections |
a = 13.1384 (13) Å | θ = 2.3–22.5° |
b = 13.3144 (19) Å | µ = 0.90 mm−1 |
c = 14.0120 (9) Å | T = 293 K |
β = 110.198 (6)° | Block, red |
V = 2300.4 (4) Å3 | 0.24 × 0.22 × 0.20 mm |
Z = 4 |
Bruker APEXII CCD diffractometer | 4034 independent reflections |
Radiation source: fine-focus sealed tube | 2827 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.087 |
φ and ω scans | θmax = 25.0°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −15→15 |
Tmin = 0.812, Tmax = 0.840 | k = −15→14 |
12275 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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.140 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0689P)2] where P = (Fo2 + 2Fc2)/3 |
4034 reflections | (Δ/σ)max = 0.001 |
293 parameters | Δρmax = 0.70 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
[Co(C18H18N2O4)Cl(H2O)]·C3H7NO | V = 2300.4 (4) Å3 |
Mr = 511.84 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.1384 (13) Å | µ = 0.90 mm−1 |
b = 13.3144 (19) Å | T = 293 K |
c = 14.0120 (9) Å | 0.24 × 0.22 × 0.20 mm |
β = 110.198 (6)° |
Bruker APEXII CCD diffractometer | 4034 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 2827 reflections with I > 2σ(I) |
Tmin = 0.812, Tmax = 0.840 | Rint = 0.087 |
12275 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | 0 restraints |
wR(F2) = 0.140 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.70 e Å−3 |
4034 reflections | Δρmin = −0.39 e Å−3 |
293 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles |
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 | 0.90848 (4) | 0.14998 (3) | 0.92275 (3) | 0.0496 (2) | |
Cl5 | 0.92093 (9) | 0.30523 (7) | 0.98338 (7) | 0.0715 (4) | |
O1 | 0.90866 (18) | 0.09840 (17) | 1.04805 (16) | 0.0522 (8) | |
O2 | 1.06060 (18) | 0.13508 (17) | 0.97448 (17) | 0.0539 (8) | |
O3 | 0.94754 (18) | 0.02362 (19) | 1.22469 (16) | 0.0611 (9) | |
O4 | 1.26159 (19) | 0.1281 (2) | 1.08943 (19) | 0.0673 (10) | |
O5 | 0.89466 (17) | 0.01086 (16) | 0.86955 (15) | 0.0533 (8) | |
N1 | 0.9079 (2) | 0.1957 (2) | 0.7953 (2) | 0.0535 (10) | |
N2 | 0.7567 (2) | 0.1638 (2) | 0.8674 (2) | 0.0569 (10) | |
C1 | 1.1284 (3) | 0.1773 (2) | 0.9372 (3) | 0.0515 (11) | |
C2 | 1.2396 (3) | 0.1745 (3) | 0.9968 (3) | 0.0606 (14) | |
C3 | 1.3174 (3) | 0.2134 (3) | 0.9619 (3) | 0.0751 (17) | |
C4 | 1.2861 (4) | 0.2591 (4) | 0.8665 (4) | 0.0822 (17) | |
C5 | 1.1799 (4) | 0.2652 (3) | 0.8074 (3) | 0.0737 (17) | |
C6 | 1.0988 (3) | 0.2252 (3) | 0.8418 (3) | 0.0578 (12) | |
C7 | 0.9889 (3) | 0.2273 (3) | 0.7741 (3) | 0.0594 (14) | |
C8 | 0.7993 (3) | 0.1895 (3) | 0.7181 (3) | 0.0698 (16) | |
C9 | 0.7199 (3) | 0.2143 (3) | 0.7682 (3) | 0.0743 (16) | |
C10 | 0.6880 (3) | 0.1424 (3) | 0.9111 (3) | 0.0586 (12) | |
C11 | 0.7150 (3) | 0.1020 (3) | 1.0106 (3) | 0.0541 (12) | |
C12 | 0.6303 (3) | 0.0808 (3) | 1.0478 (3) | 0.0663 (14) | |
C13 | 0.6511 (3) | 0.0418 (3) | 1.1417 (3) | 0.0727 (17) | |
C14 | 0.7565 (3) | 0.0214 (3) | 1.2036 (3) | 0.0665 (16) | |
C15 | 0.8411 (3) | 0.0409 (3) | 1.1708 (2) | 0.0543 (11) | |
C16 | 0.8231 (3) | 0.0820 (2) | 1.0729 (2) | 0.0499 (11) | |
C17 | 0.9757 (3) | −0.0122 (3) | 1.3268 (2) | 0.0700 (16) | |
C18 | 1.3706 (3) | 0.1101 (4) | 1.1502 (3) | 0.0778 (17) | |
O6 | 0.5199 (4) | 0.9040 (5) | 0.2962 (4) | 0.192 (3) | |
N3 | 0.6662 (5) | 0.9626 (6) | 0.4178 (4) | 0.134 (3) | |
C19 | 0.7766 (5) | 0.9485 (6) | 0.4778 (4) | 0.168 (4) | |
C20 | 0.6114 (8) | 1.0463 (11) | 0.4401 (8) | 0.236 (8) | |
C21 | 0.6116 (6) | 0.9002 (6) | 0.3479 (5) | 0.141 (3) | |
H3 | 1.39040 | 0.20920 | 1.00180 | 0.0900* | |
H4 | 1.33860 | 0.28570 | 0.84310 | 0.0980* | |
H5 | 1.16020 | 0.29590 | 0.74400 | 0.0890* | |
H5A | 0.87980 | −0.03370 | 0.91700 | 0.0800* | |
H5B | 0.96130 | −0.00860 | 0.86080 | 0.0800* | |
H7 | 0.97560 | 0.25380 | 0.70950 | 0.0710* | |
H8A | 0.78620 | 0.12230 | 0.68970 | 0.0840* | |
H8B | 0.79280 | 0.23660 | 0.66340 | 0.0840* | |
H9A | 0.71680 | 0.28640 | 0.77700 | 0.0890* | |
H9B | 0.64820 | 0.19090 | 0.72730 | 0.0890* | |
H10 | 0.61510 | 0.15420 | 0.87490 | 0.0700* | |
H12 | 0.55890 | 0.09390 | 1.00710 | 0.0790* | |
H13 | 0.59420 | 0.02860 | 1.16480 | 0.0870* | |
H14 | 0.76990 | −0.00570 | 1.26800 | 0.0800* | |
H17A | 0.95880 | 0.03830 | 1.36800 | 0.0840* | |
H17B | 1.05190 | −0.02680 | 1.35360 | 0.0840* | |
H17C | 0.93540 | −0.07210 | 1.32750 | 0.0840* | |
H18A | 1.40490 | 0.07070 | 1.11250 | 0.0940* | |
H18B | 1.37300 | 0.07430 | 1.21040 | 0.0940* | |
H18C | 1.40800 | 0.17290 | 1.16890 | 0.0940* | |
H19A | 0.80250 | 0.88730 | 0.45800 | 0.2020* | |
H19B | 0.78360 | 0.94460 | 0.54820 | 0.2020* | |
H19C | 0.81850 | 1.00400 | 0.46800 | 0.2020* | |
H20A | 0.53720 | 1.04620 | 0.39530 | 0.3540* | |
H20B | 0.64610 | 1.10710 | 0.43080 | 0.3540* | |
H20C | 0.61390 | 1.04200 | 0.50920 | 0.3540* | |
H21 | 0.65020 | 0.84530 | 0.33730 | 0.1690* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.0578 (3) | 0.0354 (3) | 0.0523 (3) | 0.0018 (2) | 0.0148 (2) | 0.0031 (2) |
Cl5 | 0.0952 (8) | 0.0478 (5) | 0.0697 (6) | 0.0027 (5) | 0.0262 (5) | −0.0019 (4) |
O1 | 0.0540 (13) | 0.0457 (14) | 0.0556 (13) | 0.0024 (11) | 0.0173 (11) | 0.0083 (10) |
O2 | 0.0593 (14) | 0.0420 (13) | 0.0586 (14) | −0.0011 (11) | 0.0179 (11) | 0.0085 (10) |
O3 | 0.0649 (16) | 0.0616 (16) | 0.0533 (14) | 0.0079 (13) | 0.0158 (12) | 0.0069 (11) |
O4 | 0.0587 (16) | 0.0688 (18) | 0.0702 (16) | 0.0024 (13) | 0.0171 (13) | 0.0054 (13) |
O5 | 0.0599 (14) | 0.0371 (12) | 0.0615 (13) | −0.0006 (11) | 0.0192 (11) | 0.0021 (10) |
N1 | 0.0674 (19) | 0.0372 (16) | 0.0520 (16) | −0.0020 (14) | 0.0157 (15) | 0.0019 (12) |
N2 | 0.0667 (19) | 0.0432 (17) | 0.0551 (17) | 0.0056 (14) | 0.0136 (16) | 0.0072 (13) |
C1 | 0.064 (2) | 0.0339 (18) | 0.060 (2) | −0.0031 (16) | 0.0259 (19) | −0.0050 (15) |
C2 | 0.069 (3) | 0.050 (2) | 0.067 (2) | −0.0035 (19) | 0.029 (2) | −0.0060 (17) |
C3 | 0.072 (3) | 0.070 (3) | 0.087 (3) | −0.008 (2) | 0.032 (2) | −0.006 (2) |
C4 | 0.083 (3) | 0.082 (3) | 0.095 (3) | −0.016 (3) | 0.048 (3) | −0.003 (3) |
C5 | 0.097 (3) | 0.059 (3) | 0.074 (3) | −0.012 (2) | 0.041 (3) | 0.0032 (19) |
C6 | 0.070 (2) | 0.044 (2) | 0.062 (2) | −0.0035 (18) | 0.026 (2) | −0.0028 (16) |
C7 | 0.086 (3) | 0.041 (2) | 0.052 (2) | 0.0026 (19) | 0.025 (2) | 0.0048 (15) |
C8 | 0.082 (3) | 0.066 (3) | 0.052 (2) | −0.002 (2) | 0.011 (2) | 0.0086 (17) |
C9 | 0.069 (3) | 0.074 (3) | 0.067 (2) | 0.006 (2) | 0.007 (2) | 0.017 (2) |
C10 | 0.055 (2) | 0.046 (2) | 0.066 (2) | 0.0043 (17) | 0.0098 (19) | 0.0027 (16) |
C11 | 0.056 (2) | 0.044 (2) | 0.059 (2) | 0.0013 (17) | 0.0158 (17) | −0.0028 (15) |
C12 | 0.056 (2) | 0.069 (3) | 0.072 (2) | 0.0048 (19) | 0.0197 (19) | −0.002 (2) |
C13 | 0.070 (3) | 0.080 (3) | 0.075 (3) | 0.001 (2) | 0.034 (2) | −0.001 (2) |
C14 | 0.077 (3) | 0.066 (3) | 0.060 (2) | 0.002 (2) | 0.028 (2) | 0.0043 (18) |
C15 | 0.064 (2) | 0.0418 (19) | 0.056 (2) | 0.0031 (17) | 0.0192 (18) | −0.0021 (15) |
C16 | 0.060 (2) | 0.0353 (18) | 0.056 (2) | 0.0043 (16) | 0.0222 (17) | −0.0025 (14) |
C17 | 0.083 (3) | 0.067 (3) | 0.054 (2) | 0.010 (2) | 0.016 (2) | 0.0007 (18) |
C18 | 0.061 (3) | 0.076 (3) | 0.086 (3) | 0.004 (2) | 0.012 (2) | −0.002 (2) |
O6 | 0.128 (4) | 0.242 (7) | 0.143 (4) | −0.093 (4) | −0.033 (3) | 0.061 (4) |
N3 | 0.121 (4) | 0.159 (6) | 0.096 (3) | −0.056 (4) | 0.005 (3) | 0.032 (3) |
C19 | 0.148 (6) | 0.189 (8) | 0.115 (4) | −0.095 (6) | −0.021 (4) | 0.057 (5) |
C20 | 0.215 (11) | 0.292 (18) | 0.224 (11) | −0.008 (10) | 0.105 (8) | −0.032 (11) |
C21 | 0.138 (6) | 0.134 (6) | 0.103 (4) | −0.075 (5) | −0.019 (4) | 0.041 (4) |
Co1—Cl5 | 2.2193 (11) | C11—C12 | 1.411 (6) |
Co1—O1 | 1.885 (2) | C11—C16 | 1.412 (5) |
Co1—O2 | 1.887 (3) | C12—C13 | 1.352 (6) |
Co1—O5 | 1.982 (2) | C13—C14 | 1.384 (6) |
Co1—N1 | 1.884 (3) | C14—C15 | 1.366 (6) |
Co1—N2 | 1.883 (3) | C15—C16 | 1.419 (4) |
O1—C16 | 1.305 (5) | C3—H3 | 0.9300 |
O2—C1 | 1.305 (5) | C4—H4 | 0.9300 |
O3—C15 | 1.360 (4) | C5—H5 | 0.9300 |
O3—C17 | 1.430 (4) | C7—H7 | 0.9300 |
O4—C2 | 1.375 (5) | C8—H8B | 0.9700 |
O4—C18 | 1.411 (5) | C8—H8A | 0.9700 |
O5—H5A | 0.9600 | C9—H9B | 0.9700 |
O5—H5B | 0.9600 | C9—H9A | 0.9700 |
O6—C21 | 1.173 (9) | C10—H10 | 0.9300 |
N1—C7 | 1.271 (5) | C12—H12 | 0.9300 |
N1—C8 | 1.465 (5) | C13—H13 | 0.9300 |
N2—C10 | 1.286 (5) | C14—H14 | 0.9300 |
N2—C9 | 1.468 (5) | C17—H17A | 0.9600 |
N3—C19 | 1.416 (9) | C17—H17B | 0.9600 |
N3—C20 | 1.419 (15) | C17—H17C | 0.9600 |
N3—C21 | 1.296 (10) | C18—H18B | 0.9600 |
C1—C6 | 1.409 (5) | C18—H18C | 0.9600 |
C1—C2 | 1.411 (6) | C18—H18A | 0.9600 |
C2—C3 | 1.378 (6) | C19—H19A | 0.9600 |
C3—C4 | 1.395 (7) | C19—H19B | 0.9600 |
C4—C5 | 1.357 (7) | C19—H19C | 0.9600 |
C5—C6 | 1.416 (7) | C20—H20A | 0.9600 |
C6—C7 | 1.428 (6) | C20—H20B | 0.9600 |
C8—C9 | 1.482 (6) | C20—H20C | 0.9600 |
C10—C11 | 1.420 (6) | C21—H21 | 0.9300 |
Cl5—Co1—O1 | 90.38 (7) | C11—C16—C15 | 117.8 (4) |
Cl5—Co1—O2 | 91.29 (8) | O1—C16—C15 | 116.8 (3) |
Cl5—Co1—O5 | 178.77 (8) | O1—C16—C11 | 125.4 (3) |
Cl5—Co1—N1 | 92.15 (9) | C2—C3—H3 | 120.00 |
Cl5—Co1—N2 | 89.67 (9) | C4—C3—H3 | 120.00 |
O1—Co1—O2 | 86.75 (10) | C5—C4—H4 | 120.00 |
O1—Co1—O5 | 88.87 (9) | C3—C4—H4 | 120.00 |
O1—Co1—N1 | 177.47 (11) | C4—C5—H5 | 120.00 |
O1—Co1—N2 | 94.58 (11) | C6—C5—H5 | 120.00 |
O2—Co1—O5 | 89.63 (10) | N1—C7—H7 | 118.00 |
O2—Co1—N1 | 93.16 (11) | C6—C7—H7 | 117.00 |
O2—Co1—N2 | 178.35 (11) | C9—C8—H8B | 110.00 |
O5—Co1—N1 | 88.60 (10) | H8A—C8—H8B | 108.00 |
O5—Co1—N2 | 89.42 (11) | C9—C8—H8A | 110.00 |
N1—Co1—N2 | 85.46 (12) | N1—C8—H8A | 110.00 |
Co1—O1—C16 | 125.8 (2) | N1—C8—H8B | 110.00 |
Co1—O2—C1 | 125.4 (2) | N2—C9—H9A | 110.00 |
C15—O3—C17 | 118.2 (3) | N2—C9—H9B | 110.00 |
C2—O4—C18 | 119.0 (3) | C8—C9—H9A | 110.00 |
Co1—O5—H5A | 109.00 | C8—C9—H9B | 110.00 |
Co1—O5—H5B | 109.00 | H9A—C9—H9B | 109.00 |
H5A—O5—H5B | 110.00 | C11—C10—H10 | 117.00 |
Co1—N1—C7 | 126.8 (3) | N2—C10—H10 | 118.00 |
Co1—N1—C8 | 111.5 (2) | C11—C12—H12 | 120.00 |
C7—N1—C8 | 121.8 (3) | C13—C12—H12 | 119.00 |
C9—N2—C10 | 119.8 (3) | C12—C13—H13 | 120.00 |
Co1—N2—C10 | 126.9 (3) | C14—C13—H13 | 120.00 |
Co1—N2—C9 | 113.0 (2) | C15—C14—H14 | 120.00 |
C19—N3—C21 | 123.4 (7) | C13—C14—H14 | 120.00 |
C20—N3—C21 | 118.7 (8) | O3—C17—H17B | 109.00 |
C19—N3—C20 | 117.9 (7) | H17A—C17—H17C | 109.00 |
C2—C1—C6 | 117.6 (4) | O3—C17—H17C | 110.00 |
O2—C1—C2 | 117.5 (3) | H17A—C17—H17B | 109.00 |
O2—C1—C6 | 124.9 (4) | O3—C17—H17A | 110.00 |
O4—C2—C1 | 114.1 (3) | H17B—C17—H17C | 109.00 |
O4—C2—C3 | 124.4 (4) | O4—C18—H18C | 110.00 |
C1—C2—C3 | 121.6 (4) | H18A—C18—H18C | 109.00 |
C2—C3—C4 | 119.7 (4) | H18B—C18—H18C | 110.00 |
C3—C4—C5 | 120.8 (5) | H18A—C18—H18B | 109.00 |
C4—C5—C6 | 120.4 (4) | O4—C18—H18A | 109.00 |
C5—C6—C7 | 118.3 (4) | O4—C18—H18B | 109.00 |
C1—C6—C5 | 120.0 (4) | O6—C21—N3 | 128.4 (8) |
C1—C6—C7 | 121.6 (4) | N3—C19—H19A | 109.00 |
N1—C7—C6 | 125.1 (4) | N3—C19—H19B | 109.00 |
N1—C8—C9 | 107.6 (3) | N3—C19—H19C | 110.00 |
N2—C9—C8 | 106.9 (3) | H19A—C19—H19B | 109.00 |
N2—C10—C11 | 125.0 (4) | H19A—C19—H19C | 110.00 |
C12—C11—C16 | 119.2 (3) | H19B—C19—H19C | 109.00 |
C10—C11—C16 | 122.4 (4) | N3—C20—H20A | 109.00 |
C10—C11—C12 | 118.5 (4) | N3—C20—H20B | 109.00 |
C11—C12—C13 | 121.1 (4) | N3—C20—H20C | 109.00 |
C12—C13—C14 | 120.5 (4) | H20A—C20—H20B | 110.00 |
C13—C14—C15 | 120.4 (4) | H20A—C20—H20C | 109.00 |
O3—C15—C14 | 125.5 (3) | H20B—C20—H20C | 110.00 |
C14—C15—C16 | 121.0 (3) | O6—C21—H21 | 116.00 |
O3—C15—C16 | 113.5 (3) | N3—C21—H21 | 116.00 |
Cl5—Co1—O1—C16 | 90.4 (2) | Co1—N2—C10—C11 | −1.2 (6) |
O2—Co1—O1—C16 | −178.3 (2) | C10—N2—C9—C8 | −155.7 (3) |
O5—Co1—O1—C16 | −88.6 (2) | C19—N3—C21—O6 | 178.1 (8) |
N2—Co1—O1—C16 | 0.7 (2) | C20—N3—C21—O6 | 2.1 (13) |
Cl5—Co1—O2—C1 | −73.5 (2) | O2—C1—C6—C5 | −177.6 (3) |
O1—Co1—O2—C1 | −163.8 (3) | C2—C1—C6—C7 | 176.8 (4) |
O5—Co1—O2—C1 | 107.3 (3) | O2—C1—C2—O4 | −1.3 (5) |
N1—Co1—O2—C1 | 18.7 (3) | O2—C1—C6—C7 | −3.0 (6) |
Cl5—Co1—N1—C7 | 75.7 (3) | O2—C1—C2—C3 | 177.3 (3) |
Cl5—Co1—N1—C8 | −105.3 (2) | C2—C1—C6—C5 | 2.2 (5) |
O2—Co1—N1—C7 | −15.8 (3) | C6—C1—C2—C3 | −2.6 (5) |
O2—Co1—N1—C8 | 163.3 (2) | C6—C1—C2—O4 | 178.9 (3) |
O5—Co1—N1—C7 | −105.3 (3) | C1—C2—C3—C4 | 1.7 (6) |
O5—Co1—N1—C8 | 73.7 (2) | O4—C2—C3—C4 | −180.0 (4) |
N2—Co1—N1—C7 | 165.2 (3) | C2—C3—C4—C5 | −0.4 (7) |
N2—Co1—N1—C8 | −15.8 (2) | C3—C4—C5—C6 | 0.1 (7) |
Cl5—Co1—N2—C9 | 83.4 (2) | C4—C5—C6—C7 | −175.8 (4) |
Cl5—Co1—N2—C10 | −89.9 (3) | C4—C5—C6—C1 | −1.0 (6) |
O1—Co1—N2—C9 | 173.8 (2) | C5—C6—C7—N1 | −178.8 (4) |
O1—Co1—N2—C10 | 0.5 (3) | C1—C6—C7—N1 | 6.6 (6) |
O5—Co1—N2—C9 | −97.4 (2) | N1—C8—C9—N2 | −41.8 (4) |
O5—Co1—N2—C10 | 89.3 (3) | N2—C10—C11—C16 | 0.7 (6) |
N1—Co1—N2—C9 | −8.8 (2) | N2—C10—C11—C12 | −179.0 (4) |
N1—Co1—N2—C10 | 177.9 (3) | C10—C11—C12—C13 | 179.7 (4) |
Co1—O1—C16—C11 | −1.3 (4) | C16—C11—C12—C13 | 0.0 (6) |
Co1—O1—C16—C15 | 178.8 (2) | C12—C11—C16—C15 | 0.1 (5) |
Co1—O2—C1—C2 | 167.5 (2) | C12—C11—C16—O1 | −179.7 (3) |
Co1—O2—C1—C6 | −12.7 (5) | C10—C11—C16—O1 | 0.6 (5) |
C17—O3—C15—C16 | 176.4 (3) | C10—C11—C16—C15 | −179.5 (3) |
C17—O3—C15—C14 | −4.1 (5) | C11—C12—C13—C14 | −0.2 (6) |
C18—O4—C2—C3 | −6.1 (6) | C12—C13—C14—C15 | 0.3 (6) |
C18—O4—C2—C1 | 172.4 (3) | C13—C14—C15—C16 | −0.2 (6) |
Co1—N1—C8—C9 | 36.3 (3) | C13—C14—C15—O3 | −179.7 (4) |
C7—N1—C8—C9 | −144.6 (4) | O3—C15—C16—C11 | 179.6 (3) |
Co1—N1—C7—C6 | 6.2 (6) | C14—C15—C16—O1 | 179.8 (3) |
C8—N1—C7—C6 | −172.7 (4) | C14—C15—C16—C11 | 0.0 (5) |
Co1—N2—C9—C8 | 30.5 (4) | O3—C15—C16—O1 | −0.6 (4) |
C9—N2—C10—C11 | −174.1 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···O2i | 0.96 | 1.98 | 2.830 (3) | 146 |
O5—H5A···O4i | 0.96 | 2.22 | 2.964 (4) | 134 |
O5—H5B···O1i | 0.96 | 2.11 | 2.840 (3) | 131 |
O5—H5B···O3i | 0.96 | 1.97 | 2.854 (3) | 151 |
C9—H9B···O6ii | 0.97 | 2.47 | 3.355 (7) | 152 |
C10—H10···O6ii | 0.93 | 2.56 | 3.287 (7) | 135 |
C17—H17A···Cl5iii | 0.96 | 2.79 | 3.744 (4) | 175 |
Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+1, −y+1, −z+1; (iii) x, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Co(C18H18N2O4)Cl(H2O)]·C3H7NO |
Mr | 511.84 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 13.1384 (13), 13.3144 (19), 14.0120 (9) |
β (°) | 110.198 (6) |
V (Å3) | 2300.4 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.90 |
Crystal size (mm) | 0.24 × 0.22 × 0.20 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2003) |
Tmin, Tmax | 0.812, 0.840 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12275, 4034, 2827 |
Rint | 0.087 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.140, 1.01 |
No. of reflections | 4034 |
No. of parameters | 293 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.70, −0.39 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···O2i | 0.96 | 1.98 | 2.830 (3) | 146 |
O5—H5A···O4i | 0.96 | 2.22 | 2.964 (4) | 134 |
O5—H5B···O1i | 0.96 | 2.11 | 2.840 (3) | 131 |
O5—H5B···O3i | 0.96 | 1.97 | 2.854 (3) | 151 |
C9—H9B···O6ii | 0.97 | 2.47 | 3.355 (7) | 152 |
C10—H10···O6ii | 0.93 | 2.56 | 3.287 (7) | 135 |
C17—H17A···Cl5iii | 0.96 | 2.79 | 3.744 (4) | 175 |
Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+1, −y+1, −z+1; (iii) x, −y+1/2, z+1/2. |
Acknowledgements
The authors thank the National Natural Science Foundation of China (grant No. 20871099) and the Natural Science Foundation of Gansu Province (grant No. 0710RJZA113) for financial support. The authors also thank the Key Laboratory of Eco-Environment-Related Polymer Materials (Northwest Normal University), Ministry of Education, for financial support.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Polydentate Schiff base ligands and their metal complexes have been studied for decades (Aurangzeb et al., 1994, Hulme et al., 1997; Li et al., 2008; Wang et al., 1979; Xing, 2009). Transition metal complexes of Schiff bases derived from o-vanillin have attracted more attention during past years due to their antibacterial activity (Liu et al., 1990; Viswanathamurthi et al., 2000; Yeap et al., 2003). Herein, we report on the synthesis and crystal structure of the title cobalt(III) complex.
The molecular structure of the title compound is illustrated in Fig. 1. The CoIII ion is coordinated to two N and two O atoms of the tetradentate 6,6'-dimethoxy-2,2'-[ethane-1,2-diylbis(nitrilomethanylylidene)]diphenolate ligand, a Cl- ion and one water molecule. The compound crystallized with a molecule of dimethylformamide, used as solvent. The crystal structure of the ligand has been reported previously (Xia et al., 2006), as has the monohydrate form of the title complex (Xing, 2009). The Cl5—Co1—O5 bond angle is 178.77 (7)° suggesting that the CoIII ion has a slightly distorted octahedral environment, with atoms N1, N2, O1 and O2 occupying the equatorial positions, while atoms Cl5 and O5water occupy the axial positions.
In the crystal, complex molecules are linked via O-Hwater···O hydrogen bonds to form a dimer-like arrangement. These dimers are linked via a C-H···Cl interaction, and the DMF molecule is linked to the complex molecule by C-H···O interactions (Table 1).