metal-organic compounds
Dichloridobis[5-nitro-1-trimethylsilylmethyl-1H-benzimidazole-κN3]cobalt(II) N,N-dimethylformamide solvate
aDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, bDepartment of Physics, Faculty of Arts and Sciences, Harran University, 63300 Şanlıurfa, Turkey, cDepartment of Chemistry, Faculty of Arts and Sciences, Ínönü University, 44280 Malatya, Turkey, and dDepartment of Physics, University of Sargodha, Sargodha, Pakistan
*Correspondence e-mail: akkurt@erciyes.edu.tr
The title compound, [CoCl2(C11H15N3O2Si)2]·C3H7NO, was synthesized from 5-nitro-1-trimethylsilylmethyl-1H-benzimidazole and cobalt(II) chloride in dimethylformamide. The CoII atom is coordinated in a distorted tetrahedral environment by two Cl atoms and two N atoms. In the there are a number of C—H⋯Cl and C—H⋯O hydrogen-bonding interactions between symmetry-related molecules.
Related literature
For the structures and properties of benzimidazole compounds and their metal complexes, see: Akkurt et al. (2005); Castro et al. (2002); Küçükbay et al. (1996, 2004, 2009); Liu et al. (2004); Lukevics et al. (2001); Pınar et al. (2006); Pan & Xu (2004); Türktekin et al. (2004); Tavman et al. (2005); Özdemir et al. (2005); Çetinkaya et al. (1996).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.
Supporting information
10.1107/S1600536810003922/bt5186sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536810003922/bt5186Isup2.hkl
1-(Trimethylsilylmethyl)-5-nitrobenzimidazole used in this work as a starting compounds were prepared from reaction of 5(6)-methylbenzimidazole, (chloromethyl)trimethylsilane and KOH under reflux in EtOH.
A solution of 1-(trimethylsilylmethyl)-5-nitrobenzimidazole (2.0 g, 8.02 mmol) and cobalt(II) chloride (0.52 g, 4.01 mmol) in DMF (4 ml) was heated under reflux for 2 h. The mixture was then cooled to room temperature, after which the solvent was then removed from the filtrate in vacuo. The precipitate was then crystallized from EtOH / DMF(2:1). Yield : 2.30 g, 91%; m.p.: 473-474 K. Analysis calculated for C22H30N6O4Si2CoCl2.HCON(CH3)2 : C 42.80, H 5.32, N 13.97%. Found: C 42.79, H 5.31, N 13.92%. IR : ν(C=N): 1523 cm-1. 1H-NMR (DMSO-d6): δ = 7.97 ppm (s, 2H, N=CH—N), 6.39 (m, 6H, Ar—H), 4.25 (m, 4H, CH2Si), -0.27 (s, 18H, Si (CH3)3).
All H atoms were placed at calculated positions and treated as riding atoms, with C—H = 0.95–0.99 Å, and Uiso(H) = 1.2 or 1.5Ueq(C).
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).Fig. 1. The title molecule showing the atom-labelling scheme. The probability level for the anisotropic displacement parameters is at 50%. | |
Fig. 2. View of the packing diagram of the title compound in the unit cell. Hydrogen bonds are indicated as dashed lines. |
[CoCl2(C11H15N3O2Si)2]·C3H7NO | Z = 2 |
Mr = 701.63 | F(000) = 730 |
Triclinic, P1 | Dx = 1.428 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.8982 (4) Å | Cell parameters from 4864 reflections |
b = 11.6936 (5) Å | θ = 5.4–51.0° |
c = 15.9293 (6) Å | µ = 0.81 mm−1 |
α = 106.041 (2)° | T = 100 K |
β = 107.408 (2)° | Plate, blue |
γ = 99.040 (3)° | 0.20 × 0.12 × 0.08 mm |
V = 1631.97 (12) Å3 |
Brruker APEXII QUAZAR diffractometer | 8851 independent reflections |
Radiation source: ImuS | 5342 reflections with I > 2σ(I) |
Multilayer monochromator | Rint = 0.059 |
ω and ϕ scans | θmax = 29.4°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −13→13 |
Tmin = 0.890, Tmax = 0.937 | k = −16→16 |
30895 measured reflections | l = −21→21 |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0506P)2 + 0.0752P] where P = (Fo2 + 2Fc2)/3 |
8851 reflections | (Δ/σ)max = 0.001 |
387 parameters | Δρmax = 0.90 e Å−3 |
0 restraints | Δρmin = −0.48 e Å−3 |
[CoCl2(C11H15N3O2Si)2]·C3H7NO | γ = 99.040 (3)° |
Mr = 701.63 | V = 1631.97 (12) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.8982 (4) Å | Mo Kα radiation |
b = 11.6936 (5) Å | µ = 0.81 mm−1 |
c = 15.9293 (6) Å | T = 100 K |
α = 106.041 (2)° | 0.20 × 0.12 × 0.08 mm |
β = 107.408 (2)° |
Brruker APEXII QUAZAR diffractometer | 8851 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 5342 reflections with I > 2σ(I) |
Tmin = 0.890, Tmax = 0.937 | Rint = 0.059 |
30895 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.90 e Å−3 |
8851 reflections | Δρmin = −0.48 e Å−3 |
387 parameters |
Experimental. Data were collected on an APEX II QUAZAR diffractometer equipped with a brilliant, high intense IµS (microfocus source) with multilayer mirrors for monochromation and collimation. |
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 on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | 0.38557 (4) | 0.69835 (4) | 0.77352 (3) | 0.0194 (1) | |
Cl1 | 0.23442 (8) | 0.51641 (7) | 0.74255 (6) | 0.0299 (2) | |
Cl2 | 0.28764 (9) | 0.80333 (7) | 0.68299 (5) | 0.0305 (3) | |
Si1 | 0.80522 (9) | 0.66034 (8) | 0.52977 (6) | 0.0220 (3) | |
Si2 | 0.76085 (9) | 0.79463 (8) | 1.19186 (6) | 0.0242 (3) | |
O1 | 0.6900 (3) | 0.3815 (2) | 0.93714 (16) | 0.0374 (8) | |
O2 | 0.9030 (3) | 0.3653 (2) | 0.93302 (19) | 0.0490 (10) | |
O3 | −0.0582 (2) | 0.8517 (2) | 0.90291 (16) | 0.0357 (8) | |
O4 | −0.0395 (2) | 0.8620 (2) | 1.04422 (17) | 0.0393 (8) | |
N1 | 0.5723 (3) | 0.6770 (2) | 0.75277 (16) | 0.0202 (8) | |
N2 | 0.7576 (3) | 0.7092 (2) | 0.70128 (16) | 0.0210 (8) | |
N3 | 0.7937 (3) | 0.4046 (2) | 0.91233 (19) | 0.0310 (9) | |
N4 | 0.4540 (2) | 0.7981 (2) | 0.91071 (16) | 0.0183 (7) | |
N5 | 0.6010 (2) | 0.8884 (2) | 1.06061 (15) | 0.0172 (7) | |
N6 | 0.0135 (3) | 0.8609 (2) | 0.98339 (19) | 0.0264 (8) | |
C1 | 0.6695 (3) | 0.6074 (3) | 0.78068 (19) | 0.0206 (9) | |
C2 | 0.6672 (3) | 0.5322 (3) | 0.8338 (2) | 0.0239 (9) | |
C3 | 0.7870 (3) | 0.4827 (3) | 0.8532 (2) | 0.0240 (10) | |
C4 | 0.9025 (3) | 0.5029 (3) | 0.8219 (2) | 0.0262 (10) | |
C5 | 0.9033 (3) | 0.5751 (3) | 0.7674 (2) | 0.0249 (10) | |
C6 | 0.7850 (3) | 0.6276 (3) | 0.74777 (19) | 0.0209 (9) | |
C7 | 0.6315 (3) | 0.7364 (3) | 0.70664 (19) | 0.0211 (9) | |
C8 | 0.8477 (3) | 0.7615 (3) | 0.6555 (2) | 0.0233 (9) | |
C9 | 0.8366 (4) | 0.5082 (3) | 0.5292 (2) | 0.0316 (11) | |
C10 | 0.9278 (3) | 0.7459 (3) | 0.4868 (2) | 0.0286 (10) | |
C11 | 0.6093 (3) | 0.6419 (3) | 0.4624 (2) | 0.0301 (11) | |
C12 | 0.3698 (3) | 0.8356 (3) | 0.96419 (19) | 0.0173 (9) | |
C13 | 0.2206 (3) | 0.8261 (3) | 0.9372 (2) | 0.0190 (9) | |
C14 | 0.1713 (3) | 0.8717 (3) | 1.0084 (2) | 0.0215 (9) | |
C15 | 0.2602 (3) | 0.9252 (3) | 1.1030 (2) | 0.0221 (9) | |
C16 | 0.4089 (3) | 0.9373 (3) | 1.1298 (2) | 0.0206 (9) | |
C17 | 0.4614 (3) | 0.8913 (3) | 1.05910 (19) | 0.0167 (8) | |
C18 | 0.5901 (3) | 0.8324 (3) | 0.97189 (19) | 0.0176 (8) | |
C19 | 0.7347 (3) | 0.9258 (3) | 1.14482 (19) | 0.0204 (9) | |
C20 | 0.6391 (3) | 0.7803 (3) | 1.2593 (2) | 0.0302 (11) | |
C21 | 0.9569 (4) | 0.8365 (4) | 1.2669 (3) | 0.0517 (16) | |
C22 | 0.7128 (4) | 0.6516 (3) | 1.0898 (2) | 0.0424 (14) | |
O5 | 0.3510 (3) | 1.0259 (2) | 0.34832 (19) | 0.0470 (10) | |
N7 | 0.3118 (3) | 0.8861 (2) | 0.41855 (17) | 0.0256 (8) | |
C23 | 0.3349 (4) | 0.9199 (4) | 0.3519 (3) | 0.0478 (16) | |
C24 | 0.2906 (4) | 0.9746 (4) | 0.4965 (3) | 0.0484 (14) | |
C25 | 0.2834 (4) | 0.7605 (3) | 0.4171 (3) | 0.0472 (14) | |
H2 | 0.58920 | 0.51540 | 0.85550 | 0.0290* | |
H4 | 0.98130 | 0.46640 | 0.83840 | 0.0310* | |
H5 | 0.98000 | 0.58890 | 0.74420 | 0.0300* | |
H7 | 0.58970 | 0.79200 | 0.68020 | 0.0250* | |
H8A | 0.95250 | 0.77410 | 0.69220 | 0.0280* | |
H8B | 0.83170 | 0.84310 | 0.65610 | 0.0280* | |
H9A | 0.81830 | 0.45610 | 0.46500 | 0.0470* | |
H9B | 0.76970 | 0.46860 | 0.55370 | 0.0470* | |
H9C | 0.93820 | 0.51920 | 0.56880 | 0.0470* | |
H10A | 1.03020 | 0.76020 | 0.52660 | 0.0430* | |
H10B | 0.90560 | 0.82520 | 0.48890 | 0.0430* | |
H10C | 0.91240 | 0.69750 | 0.42220 | 0.0430* | |
H11A | 0.59310 | 0.72290 | 0.46410 | 0.0450* | |
H11B | 0.54730 | 0.60370 | 0.49030 | 0.0450* | |
H11C | 0.58410 | 0.58930 | 0.39730 | 0.0450* | |
H13 | 0.15650 | 0.79030 | 0.87350 | 0.0230* | |
H15 | 0.21820 | 0.95320 | 1.14870 | 0.0270* | |
H16 | 0.47250 | 0.97530 | 1.19340 | 0.0250* | |
H18 | 0.67190 | 0.81890 | 0.95490 | 0.0210* | |
H19A | 0.72860 | 0.99600 | 1.19400 | 0.0250* | |
H19B | 0.82100 | 0.95400 | 1.12940 | 0.0250* | |
H20A | 0.65820 | 0.71800 | 1.28850 | 0.0450* | |
H20B | 0.53650 | 0.75540 | 1.21700 | 0.0450* | |
H20C | 0.65840 | 0.85980 | 1.30800 | 0.0450* | |
H21A | 0.97770 | 0.76980 | 1.29050 | 0.0780* | |
H21B | 0.97900 | 0.91240 | 1.31980 | 0.0780* | |
H21C | 1.01770 | 0.84960 | 1.23020 | 0.0780* | |
H22A | 0.77640 | 0.66230 | 1.05430 | 0.0640* | |
H22B | 0.61020 | 0.63470 | 1.04940 | 0.0640* | |
H22C | 0.72650 | 0.58240 | 1.11190 | 0.0640* | |
H23 | 0.33990 | 0.85760 | 0.30080 | 0.0580* | |
H24A | 0.33100 | 1.05880 | 0.50050 | 0.0720* | |
H24B | 0.34120 | 0.96270 | 0.55530 | 0.0720* | |
H24C | 0.18560 | 0.96110 | 0.48560 | 0.0720* | |
H25A | 0.18070 | 0.73140 | 0.40970 | 0.0710* | |
H25B | 0.34760 | 0.75680 | 0.47610 | 0.0710* | |
H25C | 0.30270 | 0.70800 | 0.36470 | 0.0710* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.0190 (2) | 0.0224 (2) | 0.0177 (2) | 0.0079 (2) | 0.0067 (2) | 0.0069 (2) |
Cl1 | 0.0287 (4) | 0.0262 (4) | 0.0359 (4) | 0.0061 (3) | 0.0135 (4) | 0.0110 (4) |
Cl2 | 0.0374 (5) | 0.0281 (4) | 0.0214 (4) | 0.0142 (4) | 0.0023 (3) | 0.0075 (3) |
Si1 | 0.0215 (5) | 0.0251 (5) | 0.0226 (4) | 0.0078 (4) | 0.0107 (4) | 0.0090 (4) |
Si2 | 0.0231 (5) | 0.0326 (5) | 0.0214 (4) | 0.0123 (4) | 0.0080 (4) | 0.0135 (4) |
O1 | 0.0466 (15) | 0.0345 (14) | 0.0415 (14) | 0.0148 (12) | 0.0206 (12) | 0.0211 (12) |
O2 | 0.0418 (15) | 0.0509 (17) | 0.0700 (19) | 0.0243 (13) | 0.0154 (14) | 0.0429 (15) |
O3 | 0.0227 (12) | 0.0408 (15) | 0.0360 (14) | 0.0129 (11) | 0.0039 (11) | 0.0066 (12) |
O4 | 0.0273 (13) | 0.0520 (16) | 0.0509 (15) | 0.0176 (12) | 0.0260 (12) | 0.0193 (13) |
N1 | 0.0220 (13) | 0.0228 (14) | 0.0194 (13) | 0.0090 (11) | 0.0087 (11) | 0.0094 (11) |
N2 | 0.0212 (13) | 0.0264 (14) | 0.0209 (13) | 0.0091 (11) | 0.0118 (11) | 0.0102 (11) |
N3 | 0.0365 (17) | 0.0254 (15) | 0.0351 (16) | 0.0097 (13) | 0.0128 (14) | 0.0157 (13) |
N4 | 0.0162 (13) | 0.0227 (13) | 0.0195 (12) | 0.0071 (11) | 0.0082 (10) | 0.0097 (11) |
N5 | 0.0160 (12) | 0.0194 (13) | 0.0182 (12) | 0.0076 (10) | 0.0055 (10) | 0.0086 (10) |
N6 | 0.0215 (14) | 0.0193 (14) | 0.0369 (16) | 0.0071 (11) | 0.0116 (13) | 0.0054 (12) |
C1 | 0.0240 (16) | 0.0192 (16) | 0.0168 (15) | 0.0085 (13) | 0.0056 (13) | 0.0040 (12) |
C2 | 0.0283 (17) | 0.0217 (16) | 0.0220 (16) | 0.0045 (14) | 0.0102 (14) | 0.0078 (13) |
C3 | 0.0320 (18) | 0.0171 (16) | 0.0220 (16) | 0.0087 (14) | 0.0049 (14) | 0.0094 (13) |
C4 | 0.0234 (17) | 0.0263 (17) | 0.0272 (17) | 0.0097 (14) | 0.0057 (14) | 0.0085 (14) |
C5 | 0.0205 (16) | 0.0278 (18) | 0.0256 (16) | 0.0079 (14) | 0.0082 (13) | 0.0071 (14) |
C6 | 0.0200 (16) | 0.0227 (16) | 0.0199 (15) | 0.0073 (13) | 0.0060 (13) | 0.0075 (13) |
C7 | 0.0236 (16) | 0.0269 (17) | 0.0176 (15) | 0.0119 (14) | 0.0102 (13) | 0.0089 (13) |
C8 | 0.0241 (16) | 0.0250 (17) | 0.0259 (16) | 0.0063 (14) | 0.0148 (14) | 0.0102 (14) |
C9 | 0.043 (2) | 0.0286 (19) | 0.0313 (18) | 0.0171 (16) | 0.0195 (16) | 0.0115 (15) |
C10 | 0.0207 (16) | 0.038 (2) | 0.0291 (17) | 0.0065 (15) | 0.0111 (14) | 0.0130 (15) |
C11 | 0.0245 (17) | 0.034 (2) | 0.0329 (18) | 0.0062 (15) | 0.0098 (15) | 0.0144 (16) |
C12 | 0.0171 (15) | 0.0176 (15) | 0.0203 (15) | 0.0058 (12) | 0.0072 (12) | 0.0099 (12) |
C13 | 0.0186 (15) | 0.0161 (15) | 0.0221 (15) | 0.0048 (12) | 0.0034 (12) | 0.0103 (12) |
C14 | 0.0169 (15) | 0.0194 (16) | 0.0334 (17) | 0.0078 (13) | 0.0117 (13) | 0.0125 (14) |
C15 | 0.0254 (16) | 0.0208 (16) | 0.0259 (16) | 0.0078 (13) | 0.0153 (14) | 0.0092 (13) |
C16 | 0.0241 (16) | 0.0216 (16) | 0.0185 (15) | 0.0088 (13) | 0.0094 (13) | 0.0072 (13) |
C17 | 0.0174 (15) | 0.0156 (15) | 0.0200 (14) | 0.0062 (12) | 0.0072 (12) | 0.0088 (12) |
C18 | 0.0200 (15) | 0.0193 (15) | 0.0191 (14) | 0.0084 (13) | 0.0112 (13) | 0.0085 (12) |
C19 | 0.0175 (15) | 0.0226 (16) | 0.0192 (15) | 0.0053 (13) | 0.0053 (12) | 0.0056 (13) |
C20 | 0.0287 (18) | 0.038 (2) | 0.0277 (17) | 0.0101 (16) | 0.0114 (14) | 0.0151 (16) |
C21 | 0.026 (2) | 0.088 (3) | 0.058 (3) | 0.020 (2) | 0.0110 (19) | 0.052 (3) |
C22 | 0.074 (3) | 0.036 (2) | 0.038 (2) | 0.030 (2) | 0.032 (2) | 0.0223 (18) |
O5 | 0.0476 (16) | 0.0460 (16) | 0.0694 (19) | 0.0174 (13) | 0.0287 (14) | 0.0420 (15) |
N7 | 0.0230 (14) | 0.0266 (15) | 0.0286 (14) | 0.0060 (12) | 0.0061 (12) | 0.0153 (12) |
C23 | 0.039 (2) | 0.062 (3) | 0.055 (3) | 0.018 (2) | 0.020 (2) | 0.033 (2) |
C24 | 0.056 (3) | 0.044 (2) | 0.041 (2) | 0.012 (2) | 0.018 (2) | 0.0085 (19) |
C25 | 0.045 (2) | 0.045 (2) | 0.065 (3) | 0.0190 (19) | 0.021 (2) | 0.034 (2) |
Co1—Cl1 | 2.2330 (10) | C14—C15 | 1.396 (4) |
Co1—Cl2 | 2.2455 (9) | C15—C16 | 1.376 (4) |
Co1—N1 | 2.013 (3) | C16—C17 | 1.390 (4) |
Co1—N4 | 2.013 (2) | C2—H2 | 0.9500 |
Si1—C8 | 1.902 (3) | C4—H4 | 0.9500 |
Si1—C9 | 1.852 (4) | C5—H5 | 0.9500 |
Si1—C10 | 1.854 (3) | C7—H7 | 0.9500 |
Si1—C11 | 1.859 (3) | C8—H8B | 0.9900 |
Si2—C19 | 1.904 (4) | C8—H8A | 0.9900 |
Si2—C20 | 1.856 (3) | C9—H9A | 0.9800 |
Si2—C21 | 1.851 (4) | C9—H9B | 0.9800 |
Si2—C22 | 1.858 (3) | C9—H9C | 0.9800 |
O1—N3 | 1.224 (4) | C10—H10A | 0.9800 |
O2—N3 | 1.232 (4) | C10—H10B | 0.9800 |
O3—N6 | 1.231 (4) | C10—H10C | 0.9800 |
O4—N6 | 1.230 (4) | C11—H11B | 0.9800 |
O5—C23 | 1.244 (5) | C11—H11C | 0.9800 |
N1—C1 | 1.406 (4) | C11—H11A | 0.9800 |
N1—C7 | 1.333 (4) | C13—H13 | 0.9500 |
N2—C7 | 1.356 (4) | C15—H15 | 0.9500 |
N2—C8 | 1.472 (4) | C16—H16 | 0.9500 |
N2—C6 | 1.373 (4) | C18—H18 | 0.9500 |
N3—C3 | 1.477 (4) | C19—H19B | 0.9900 |
N4—C12 | 1.395 (4) | C19—H19A | 0.9900 |
N4—C18 | 1.324 (4) | C20—H20A | 0.9800 |
N5—C18 | 1.346 (4) | C20—H20B | 0.9800 |
N5—C19 | 1.474 (4) | C20—H20C | 0.9800 |
N5—C17 | 1.381 (4) | C21—H21A | 0.9800 |
N6—C14 | 1.467 (4) | C21—H21B | 0.9800 |
N7—C25 | 1.444 (5) | C21—H21C | 0.9800 |
N7—C23 | 1.298 (5) | C22—H22B | 0.9800 |
N7—C24 | 1.473 (5) | C22—H22C | 0.9800 |
C1—C6 | 1.407 (4) | C22—H22A | 0.9800 |
C1—C2 | 1.381 (5) | C23—H23 | 0.9500 |
C2—C3 | 1.390 (5) | C24—H24A | 0.9800 |
C3—C4 | 1.390 (4) | C24—H24B | 0.9800 |
C4—C5 | 1.369 (5) | C24—H24C | 0.9800 |
C5—C6 | 1.400 (5) | C25—H25A | 0.9800 |
C12—C13 | 1.386 (4) | C25—H25B | 0.9800 |
C12—C17 | 1.408 (4) | C25—H25C | 0.9800 |
C13—C14 | 1.374 (4) | ||
Co1···H2 | 3.4200 | C22···O1 | 3.338 (4) |
Co1···H13 | 3.2900 | C22···C18 | 3.333 (5) |
Cl1···N4 | 3.484 (3) | C23···C21xi | 3.446 (6) |
Cl1···C5i | 3.564 (3) | C23···C24viii | 3.557 (6) |
Cl2···N1 | 3.420 (3) | C24···C23viii | 3.557 (6) |
Cl2···C7 | 3.546 (3) | C25···C9iii | 3.597 (5) |
Cl1···H5i | 2.7900 | C5···H13v | 2.9300 |
Cl1···H22Cii | 2.8200 | C5···H8A | 2.9400 |
Cl1···H10Ciii | 2.8600 | C5···H9B | 3.0600 |
Cl1···H20Aii | 3.0600 | C6···H9B | 3.0800 |
Cl2···H7 | 3.0300 | C8···H5 | 3.0100 |
Cl2···H10Ai | 2.8400 | C9···H9Cxii | 3.0900 |
Cl2···H9Aiii | 3.0700 | C9···H5 | 3.0900 |
Cl2···H16iv | 2.9400 | C13···H19Biv | 3.0800 |
Cl2···H19Aiv | 2.6700 | C16···H20B | 3.0800 |
Si2···O4v | 3.657 (2) | C16···H19A | 2.9200 |
O1···C22 | 3.338 (4) | C18···H22B | 2.9100 |
O1···C12ii | 3.399 (4) | C19···H16 | 3.0200 |
O1···C17ii | 3.329 (4) | C23···H24Bviii | 3.0000 |
O2···C14ii | 3.208 (4) | C23···H21Cxi | 2.9900 |
O2···O4ii | 3.223 (4) | C24···H20Civ | 3.0200 |
O2···O2vi | 3.178 (4) | C25···H11A | 3.0600 |
O2···C15ii | 3.335 (4) | C25···H9Biii | 2.8400 |
O3···C5i | 3.245 (4) | H2···O1 | 2.4500 |
O3···C1i | 3.253 (4) | H2···Co1 | 3.4200 |
O3···O4vii | 3.129 (3) | H4···O2 | 2.3800 |
O3···N2i | 3.000 (3) | H5···H13v | 2.5900 |
O3···C7i | 3.413 (4) | H5···H9C | 2.5700 |
O3···C6i | 2.869 (4) | H5···Cl1v | 2.7900 |
O3···N6vii | 3.234 (4) | H5···C8 | 3.0100 |
O4···O3vii | 3.129 (3) | H5···C9 | 3.0900 |
O4···Si2i | 3.657 (2) | H5···H8A | 2.5500 |
O4···O2ii | 3.223 (4) | H7···Cl2 | 3.0300 |
O4···C19i | 3.182 (4) | H7···H8B | 2.5400 |
O5···C8viii | 3.406 (4) | H7···O5viii | 2.3200 |
O5···C7viii | 3.132 (4) | H8A···C5 | 2.9400 |
O1···H2 | 2.4500 | H8A···H5 | 2.5500 |
O1···H20Bii | 2.6500 | H8B···H7 | 2.5400 |
O2···H4 | 2.3800 | H8B···O5viii | 2.5400 |
O3···H13 | 2.4800 | H9A···Cl2iii | 3.0700 |
O4···H18i | 2.6800 | H9B···C5 | 3.0600 |
O4···H19Bi | 2.3800 | H9B···C6 | 3.0800 |
O4···H15 | 2.4600 | H9B···C25iii | 2.8400 |
O4···H22Ai | 2.8000 | H9B···H25Biii | 2.5600 |
O4···H21Ci | 2.8900 | H9C···H5 | 2.5700 |
O5···H8Bviii | 2.5400 | H9C···C9xii | 3.0900 |
O5···H7viii | 2.3200 | H10A···Cl2v | 2.8400 |
O5···H24A | 2.4200 | H10C···Cl1iii | 2.8600 |
O5···H15ix | 2.8700 | H11A···H24Aviii | 2.4000 |
N1···N4 | 3.166 (3) | H11A···C25 | 3.0600 |
N1···Cl2 | 3.420 (3) | H11A···H25B | 2.5800 |
N1···N2 | 2.243 (4) | H11B···H11Biii | 2.5900 |
N1···C18 | 3.397 (4) | H13···C5i | 2.9300 |
N2···O3v | 3.000 (3) | H13···Co1 | 3.2900 |
N2···N1 | 2.243 (4) | H13···O3 | 2.4800 |
N4···N5 | 2.231 (3) | H13···H5i | 2.5900 |
N4···Cl1 | 3.484 (3) | H15···O5xiii | 2.8700 |
N4···N1 | 3.166 (3) | H15···O4 | 2.4600 |
N5···N4 | 2.231 (3) | H16···Cl2iv | 2.9400 |
N5···C12iv | 3.337 (4) | H16···C19 | 3.0200 |
N6···O3vii | 3.234 (4) | H16···H19A | 2.5100 |
N6···N6vii | 3.216 (4) | H18···O4v | 2.6800 |
N5···H22B | 2.9400 | H19A···H16 | 2.5100 |
C1···O3v | 3.253 (4) | H19A···C16 | 2.9200 |
C5···C9 | 3.485 (4) | H19A···Cl2iv | 2.6700 |
C5···Cl1v | 3.564 (3) | H19B···O4v | 2.3800 |
C5···O3v | 3.245 (4) | H19B···C13iv | 3.0800 |
C6···C9 | 3.596 (4) | H20A···Cl1ii | 3.0600 |
C6···O3v | 2.869 (4) | H20B···C16 | 3.0800 |
C7···O5viii | 3.132 (4) | H20B···O1ii | 2.6500 |
C7···O3v | 3.413 (4) | H20C···C24iv | 3.0200 |
C8···O5viii | 3.406 (4) | H20C···H24Biv | 2.5600 |
C9···C6 | 3.596 (4) | H21A···H25Ax | 2.5100 |
C9···C25iii | 3.597 (5) | H21C···O4v | 2.8900 |
C9···C5 | 3.485 (4) | H21C···C23x | 2.9900 |
C12···O1ii | 3.399 (4) | H22A···O4v | 2.8000 |
C12···N5iv | 3.337 (4) | H22B···N5 | 2.9400 |
C12···C17iv | 3.532 (5) | H22B···C18 | 2.9100 |
C13···C19iv | 3.515 (5) | H22C···Cl1ii | 2.8200 |
C14···O2ii | 3.208 (4) | H23···H25C | 2.2900 |
C15···O2ii | 3.335 (4) | H24A···O5 | 2.4200 |
C16···C18iv | 3.506 (5) | H24A···H11Aviii | 2.4000 |
C17···C18iv | 3.492 (5) | H24B···H25B | 2.4100 |
C17···O1ii | 3.329 (4) | H24B···C23viii | 3.0000 |
C17···C12iv | 3.532 (5) | H24B···H20Civ | 2.5600 |
C18···C22 | 3.333 (5) | H25A···H21Axi | 2.5100 |
C18···C16iv | 3.506 (5) | H25B···H11A | 2.5800 |
C18···C17iv | 3.492 (5) | H25B···H24B | 2.4100 |
C19···C13iv | 3.515 (5) | H25B···H9Biii | 2.5600 |
C19···O4v | 3.182 (4) | H25C···H23 | 2.2900 |
C21···C23x | 3.446 (6) | ||
Cl1—Co1—Cl2 | 112.94 (4) | C4—C5—H5 | 122.00 |
Cl1—Co1—N1 | 111.06 (8) | N1—C7—H7 | 124.00 |
Cl1—Co1—N4 | 110.18 (7) | N2—C7—H7 | 123.00 |
Cl2—Co1—N1 | 106.74 (7) | Si1—C8—H8A | 109.00 |
Cl2—Co1—N4 | 111.81 (7) | H8A—C8—H8B | 108.00 |
N1—Co1—N4 | 103.67 (9) | Si1—C8—H8B | 109.00 |
C8—Si1—C9 | 108.71 (15) | N2—C8—H8A | 109.00 |
C8—Si1—C10 | 105.46 (15) | N2—C8—H8B | 109.00 |
C8—Si1—C11 | 107.76 (14) | Si1—C9—H9A | 110.00 |
C9—Si1—C10 | 113.60 (17) | Si1—C9—H9B | 109.00 |
C9—Si1—C11 | 109.95 (17) | Si1—C9—H9C | 110.00 |
C10—Si1—C11 | 111.09 (15) | H9B—C9—H9C | 109.00 |
C19—Si2—C20 | 108.88 (15) | H9A—C9—H9B | 109.00 |
C19—Si2—C21 | 106.02 (18) | H9A—C9—H9C | 110.00 |
C19—Si2—C22 | 107.56 (14) | Si1—C10—H10B | 109.00 |
C20—Si2—C21 | 111.80 (17) | H10A—C10—H10C | 109.00 |
C20—Si2—C22 | 110.98 (17) | Si1—C10—H10C | 109.00 |
C21—Si2—C22 | 111.36 (19) | H10A—C10—H10B | 110.00 |
Co1—N1—C1 | 132.6 (2) | Si1—C10—H10A | 109.00 |
Co1—N1—C7 | 122.7 (2) | H10B—C10—H10C | 109.00 |
C1—N1—C7 | 104.7 (3) | Si1—C11—H11C | 109.00 |
C6—N2—C7 | 107.3 (3) | H11A—C11—H11C | 110.00 |
C6—N2—C8 | 127.5 (3) | H11B—C11—H11C | 109.00 |
C7—N2—C8 | 125.2 (3) | H11A—C11—H11B | 109.00 |
O1—N3—O2 | 123.7 (3) | Si1—C11—H11A | 109.00 |
O1—N3—C3 | 118.3 (3) | Si1—C11—H11B | 109.00 |
O2—N3—C3 | 118.0 (3) | C14—C13—H13 | 122.00 |
Co1—N4—C12 | 128.49 (18) | C12—C13—H13 | 122.00 |
Co1—N4—C18 | 126.50 (19) | C14—C15—H15 | 120.00 |
C12—N4—C18 | 104.7 (2) | C16—C15—H15 | 120.00 |
C17—N5—C18 | 107.4 (2) | C17—C16—H16 | 122.00 |
C17—N5—C19 | 126.3 (2) | C15—C16—H16 | 122.00 |
C18—N5—C19 | 125.9 (2) | N4—C18—H18 | 123.00 |
O3—N6—O4 | 123.7 (3) | N5—C18—H18 | 123.00 |
O3—N6—C14 | 118.2 (3) | Si2—C19—H19A | 109.00 |
O4—N6—C14 | 118.1 (3) | H19A—C19—H19B | 108.00 |
C24—N7—C25 | 114.4 (3) | Si2—C19—H19B | 109.00 |
C23—N7—C24 | 120.3 (3) | N5—C19—H19A | 109.00 |
C23—N7—C25 | 124.7 (3) | N5—C19—H19B | 109.00 |
N1—C1—C6 | 108.8 (3) | Si2—C20—H20A | 109.00 |
N1—C1—C2 | 130.4 (3) | Si2—C20—H20B | 109.00 |
C2—C1—C6 | 120.8 (3) | Si2—C20—H20C | 109.00 |
C1—C2—C3 | 115.2 (3) | H20B—C20—H20C | 110.00 |
N3—C3—C2 | 118.0 (3) | H20A—C20—H20B | 109.00 |
N3—C3—C4 | 117.5 (3) | H20A—C20—H20C | 109.00 |
C2—C3—C4 | 124.6 (3) | Si2—C21—H21B | 109.00 |
C3—C4—C5 | 120.3 (3) | H21A—C21—H21C | 110.00 |
C4—C5—C6 | 116.4 (3) | Si2—C21—H21C | 109.00 |
N2—C6—C1 | 106.2 (3) | H21A—C21—H21B | 109.00 |
N2—C6—C5 | 131.0 (3) | Si2—C21—H21A | 109.00 |
C1—C6—C5 | 122.7 (3) | H21B—C21—H21C | 109.00 |
N1—C7—N2 | 113.0 (3) | Si2—C22—H22C | 109.00 |
Si1—C8—N2 | 113.4 (2) | H22A—C22—H22C | 109.00 |
C13—C12—C17 | 120.4 (3) | H22B—C22—H22C | 110.00 |
N4—C12—C17 | 109.3 (3) | H22A—C22—H22B | 109.00 |
N4—C12—C13 | 130.3 (3) | Si2—C22—H22A | 109.00 |
C12—C13—C14 | 115.7 (3) | Si2—C22—H22B | 109.00 |
N6—C14—C13 | 117.6 (3) | O5—C23—N7 | 126.4 (4) |
N6—C14—C15 | 117.7 (3) | O5—C23—H23 | 117.00 |
C13—C14—C15 | 124.7 (3) | N7—C23—H23 | 117.00 |
C14—C15—C16 | 119.8 (3) | N7—C24—H24A | 109.00 |
C15—C16—C17 | 116.7 (3) | N7—C24—H24B | 109.00 |
N5—C17—C12 | 105.2 (2) | N7—C24—H24C | 109.00 |
N5—C17—C16 | 132.0 (3) | H24A—C24—H24B | 109.00 |
C12—C17—C16 | 122.8 (3) | H24A—C24—H24C | 110.00 |
N4—C18—N5 | 113.3 (3) | H24B—C24—H24C | 109.00 |
Si2—C19—N5 | 112.1 (2) | N7—C25—H25A | 109.00 |
C1—C2—H2 | 122.00 | N7—C25—H25B | 109.00 |
C3—C2—H2 | 122.00 | N7—C25—H25C | 110.00 |
C3—C4—H4 | 120.00 | H25A—C25—H25B | 109.00 |
C5—C4—H4 | 120.00 | H25A—C25—H25C | 109.00 |
C6—C5—H5 | 122.00 | H25B—C25—H25C | 109.00 |
Cl1—Co1—N1—C1 | −47.5 (3) | Co1—N4—C18—N5 | −174.0 (2) |
Cl2—Co1—N1—C1 | −171.0 (2) | C17—N5—C19—Si2 | 86.6 (3) |
N4—Co1—N1—C1 | 70.8 (3) | C18—N5—C17—C12 | −1.0 (4) |
Cl1—Co1—N1—C7 | 134.4 (2) | C19—N5—C18—N4 | 173.7 (3) |
Cl2—Co1—N1—C7 | 10.9 (2) | C19—N5—C17—C12 | −174.2 (3) |
N4—Co1—N1—C7 | −107.3 (2) | C17—N5—C18—N4 | 0.4 (4) |
Cl1—Co1—N4—C12 | −58.2 (3) | C18—N5—C19—Si2 | −85.4 (3) |
Cl2—Co1—N4—C12 | 68.3 (3) | C19—N5—C17—C16 | 6.6 (6) |
N1—Co1—N4—C12 | −177.1 (3) | C18—N5—C17—C16 | 179.8 (4) |
Cl1—Co1—N4—C18 | 114.8 (3) | O3—N6—C14—C15 | 157.4 (3) |
Cl2—Co1—N4—C18 | −118.7 (3) | O4—N6—C14—C15 | −22.3 (4) |
N1—Co1—N4—C18 | −4.1 (3) | O3—N6—C14—C13 | −23.9 (4) |
C11—Si1—C8—N2 | 60.1 (3) | O4—N6—C14—C13 | 156.4 (3) |
C10—Si1—C8—N2 | 178.8 (2) | C24—N7—C23—O5 | 4.9 (6) |
C9—Si1—C8—N2 | −59.0 (3) | C25—N7—C23—O5 | 175.4 (4) |
C22—Si2—C19—N5 | 41.2 (3) | C2—C1—C6—C5 | −0.8 (5) |
C20—Si2—C19—N5 | −79.2 (2) | N1—C1—C6—N2 | 0.5 (3) |
C21—Si2—C19—N5 | 160.4 (2) | C6—C1—C2—C3 | 1.6 (4) |
C7—N1—C1—C6 | −0.9 (3) | C2—C1—C6—N2 | −177.7 (3) |
Co1—N1—C1—C6 | −179.3 (2) | N1—C1—C6—C5 | 177.3 (3) |
C1—N1—C7—N2 | 1.0 (3) | N1—C1—C2—C3 | −176.1 (3) |
C7—N1—C1—C2 | 177.0 (3) | C1—C2—C3—C4 | −1.0 (5) |
Co1—N1—C7—N2 | 179.59 (18) | C1—C2—C3—N3 | 178.1 (3) |
Co1—N1—C1—C2 | −1.4 (5) | C2—C3—C4—C5 | −0.5 (5) |
C7—N2—C6—C1 | 0.2 (3) | N3—C3—C4—C5 | −179.6 (3) |
C8—N2—C7—N1 | −179.4 (3) | C3—C4—C5—C6 | 1.3 (5) |
C6—N2—C7—N1 | −0.8 (3) | C4—C5—C6—C1 | −0.7 (5) |
C7—N2—C8—Si1 | −95.2 (3) | C4—C5—C6—N2 | 175.3 (3) |
C8—N2—C6—C5 | 2.3 (5) | C17—C12—C13—C14 | −1.2 (5) |
C8—N2—C6—C1 | 178.8 (3) | C13—C12—C17—C16 | 1.0 (6) |
C7—N2—C6—C5 | −176.4 (3) | N4—C12—C17—N5 | 1.2 (4) |
C6—N2—C8—Si1 | 86.4 (3) | N4—C12—C17—C16 | −179.5 (3) |
O1—N3—C3—C2 | 4.0 (4) | N4—C12—C13—C14 | 179.4 (3) |
O2—N3—C3—C2 | −176.8 (3) | C13—C12—C17—N5 | −178.4 (3) |
O1—N3—C3—C4 | −176.9 (3) | C12—C13—C14—N6 | −178.5 (3) |
O2—N3—C3—C4 | 2.3 (4) | C12—C13—C14—C15 | 0.0 (6) |
C12—N4—C18—N5 | 0.3 (4) | N6—C14—C15—C16 | −180.0 (3) |
C18—N4—C12—C17 | −1.0 (4) | C13—C14—C15—C16 | 1.4 (6) |
Co1—N4—C12—C17 | 173.2 (2) | C14—C15—C16—C17 | −1.6 (5) |
Co1—N4—C12—C13 | −7.3 (5) | C15—C16—C17—N5 | 179.6 (4) |
C18—N4—C12—C13 | 178.6 (4) | C15—C16—C17—C12 | 0.5 (5) |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+2; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y+2, −z+2; (v) x+1, y, z; (vi) −x+2, −y+1, −z+2; (vii) −x, −y+2, −z+2; (viii) −x+1, −y+2, −z+1; (ix) x, y, z−1; (x) x+1, y, z+1; (xi) x−1, y, z−1; (xii) −x+2, −y+1, −z+1; (xiii) x, y, z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···Cl1v | 0.95 | 2.79 | 3.564 (3) | 140 |
C7—H7···O5viii | 0.95 | 2.32 | 3.132 (4) | 143 |
C8—H8B···O5viii | 0.99 | 2.54 | 3.406 (4) | 145 |
C19—H19A···Cl2iv | 0.99 | 2.67 | 3.659 (3) | 175 |
C19—H19B···O4v | 0.99 | 2.38 | 3.182 (4) | 137 |
C22—H22C···Cl1ii | 0.98 | 2.82 | 3.695 (3) | 149 |
C24—H24A···O5 | 0.98 | 2.42 | 2.793 (5) | 102 |
Symmetry codes: (ii) −x+1, −y+1, −z+2; (iv) −x+1, −y+2, −z+2; (v) x+1, y, z; (viii) −x+1, −y+2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [CoCl2(C11H15N3O2Si)2]·C3H7NO |
Mr | 701.63 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 9.8982 (4), 11.6936 (5), 15.9293 (6) |
α, β, γ (°) | 106.041 (2), 107.408 (2), 99.040 (3) |
V (Å3) | 1631.97 (12) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.81 |
Crystal size (mm) | 0.20 × 0.12 × 0.08 |
Data collection | |
Diffractometer | Brruker APEXII QUAZAR diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.890, 0.937 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 30895, 8851, 5342 |
Rint | 0.059 |
(sin θ/λ)max (Å−1) | 0.691 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.123, 1.02 |
No. of reflections | 8851 |
No. of parameters | 387 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.90, −0.48 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···Cl1i | 0.95 | 2.79 | 3.564 (3) | 140 |
C7—H7···O5ii | 0.95 | 2.32 | 3.132 (4) | 143 |
C8—H8B···O5ii | 0.99 | 2.54 | 3.406 (4) | 145 |
C19—H19A···Cl2iii | 0.99 | 2.67 | 3.659 (3) | 175 |
C19—H19B···O4i | 0.99 | 2.38 | 3.182 (4) | 137 |
C22—H22C···Cl1iv | 0.98 | 2.82 | 3.695 (3) | 149 |
C24—H24A···O5 | 0.98 | 2.42 | 2.793 (5) | 102 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+2, −z+1; (iii) −x+1, −y+2, −z+2; (iv) −x+1, −y+1, −z+2. |
Acknowledgements
We thank Dr Holger Ott (Bruker AXS GmbH, Karlsruhe, Germany) for the data collection. HK & NŞ also thank İnönü University Research Fund (BAPB-2008–60) for financial support of this study.
References
Akkurt, M., Karaca, S., Küçükbay, H., Orhan, E. & Büyükgüngör, O. (2005). Acta Cryst. E61, m41–m43. Web of Science CSD CrossRef IUCr Journals Google Scholar
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Castro, J., Pérez Lourido, P., Sousa-Pedrares, A., Labisbal, E., Piso, J. & García-Vázquez, J. A. (2002). Acta Cryst. C58, m319–m322. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Çetinkaya, B., Çetinkaya, E., Küçükbay, H. & Durmaz, R. (1996). Arzneim. Forsch. Drug Res. 46, 1154–1158. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Küçükbay, H., Çetinkaya, B., Guesmi, S. & Dixneuf, P. H. (1996). Organometallics, 15, 2434–2439. CrossRef CAS Web of Science Google Scholar
Küçükbay, H., Durmaz, R., Okuyucu, N., Günal, S. & Kazaz, C. (2004). Arzneim. Forsch. Drug Res. 54, 64–68. Google Scholar
Küçükbay, H., Durmaz, R., Şireci, N. & Günal, S. (2009). Asian J. Chem. 21, 6181–6189. Google Scholar
Liu, J.-W., Gao, S., Huo, L.-H. & Ng, S. W. (2004). Acta Cryst. E60, m501–m503. Web of Science CSD CrossRef IUCr Journals Google Scholar
Lukevics, E., Arsenyan, P., Shestakova, I., Domracheva, I., Nesterova, A. & Pudova, O. (2001). Eur. J. Med. Chem. 36, 507–515. Web of Science CrossRef PubMed CAS Google Scholar
Özdemir, İ., Demir, S. & Çetinkaya, B. (2005). Tetrahedron, 61, 9791–9798. Google Scholar
Pan, T.-T. & Xu, D.-J. (2004). Acta Cryst. E60, m56–m58. CSD CrossRef IUCr Journals Google Scholar
Pınar, Ş., Akkurt, M., Küçükbay, H., Orhan, E. & Büyükgüngör, O. (2006). Acta Cryst. E62, m1663–m1665. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tavman, A., Birteksöz, S. & Ötük, G. (2005). Folia Mirobio. 50, 467-472. Web of Science CrossRef CAS Google Scholar
Türktekin, S., Akkurt, M., Orhan, E., Küçükbay, F. Z., Küçükbay, H. & Büyükgüngör, O. (2004). Acta Cryst. E60, m1220–m1222. CSD CrossRef IUCr Journals Google Scholar
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.
Benzimidazole compounds and their metal complexes have been extensively investigated for their versatile properties such as biological activities (Küçükbay et al., 2004; Çetinkaya et al., 1996; Küçükbay et al., 2009; Tavman et al., 2005) and catalytic activities of their metal complexes in many organic syntheses (Küçükbay et al.,1996, Özdemir et al., 2005). Contrary to an extensive chemistry about substituted alkyl derivatives of benzimidazole, there are a limited number of studies of alkylsilyl substituted benzimidazoles (Lukevics et al., 2001). Alkylsilyl substituted benzimidazole derivatives exhibit important in vitro cytotoxicactivity. The insertion of the silicon atom into the N-alkyl chain in benzimidazoles increases the cytotoxic activity. For example,1-(3-trimethylsilylpropyl)benzimidazole inhibits carcinoma S-180 tumour growth in dose 1 mg kg-1 by 62 % (on ICR mice) (Lukevics et al., 2001). The objective of the present study was to synthesize a trimethylsilylmethyl and NO2 substituted benzimidazole CoII complex for the first time and compare it to those of related benzimidazole derivatives (Türktekin et al., 2004; Pınar et al., 2006; Akkurt et al., 2005) reported previously.
In the title molecule (Fig. 1), the CoII atom is coordinated in a distorted tetrahedral environment by two Cl atoms and two N atoms. The bond lengths involving the Co atoms are Co1—N1 = 2.013 (3), Co1—N4 = 2.013 (2), Co1—Cl1 = 2.2330 (10) and Co1—Cl2 = 2.2455 (9) Å, while the angles around the Co atom are Cl1— Co1— Cl2 = 112.94 (4), Cl1— Co1— N1 = 111.06 (8), Cl1— Co1— N4 = 110.18 (7), Cl2— Co1— N1 = 106.74 (7), Cl2— Co1— N4 = 111.81 (7) and N1— Co1— N4 = 103.67 (9)°. The average Co—N bond length of 2.013 (3)Å is almost equal to the value of 2.008 (2)Å in dichlorobis[1-(2-ethoxyethyl)-1H-benzimidazole-κN3]cobalt(II) (Türktekin et al., 2004) and 2.032 (2) Å inbis[1-(but-2-enyl)-5-nitro-1H-benzimidazole-κN3]dichlorocobalt(II) (Pınar et al., 2006).
The Co—Cl bond lengths [2.2330 (10) and 2.2455 (9) Å] are comparable to the values of 2.2525 (8)Å inquinolinium trichloro(quinoline-N)cobaltate(II) (Pan & Xu, 2004) and 2.236 (1) Å in dichlorobis(1-propylimidazolidine-2-thione-κS)cobalt(II) (Castro et al., 2002) and 2.2680 (8) in bis[1-(but-2-enyl)-5-nitro-1H-benzimidazole-κN3]dichlorocobalt(II)(Pınar et al., 2006), but shorter than the value of 2.391 (1)Å observed in aquachlorobis(1,10-phenanthroline)cobalt(II)chloride dimethyl formamide solvate (Liu et al., 2004).
The two benzimidazole ring systems N1/N2/C1–C7 and N4/N5/C12–C18 are almost planar, with maximum deviations of -0.037 (3) for C6 and -0.016 (2) for N4, respectively. The dihedral angle between them is 64.54 (10)°. The angles around the Si atoms with a distorted tetrahedral geometry rang from 106.02 (18)° to 113.60 (17)°.
The crystal structure of the title compound is stabilized by C—H···Cl and C—H···O hydrogen-bonding interactions (Fig. 2 and Table 1).