Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807061880/sj2429sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807061880/sj2429Isup2.hkl |
CCDC reference: 672769
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C)= 0.003 Å
- R factor = 0.030
- wR factor = 0.083
- Data-to-parameter ratio = 16.9
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
For general background, see: Au-Yeung & Chan (2004); Lewiński et al. (2005); Liu et al. (2006); Robin & Fromm (2006); Salmon et al. (2005); Vicente & Arcas (2005); Xu et al. (2005). For related structures, see: Ni et al. (2005); Iyere et al. (2004); Peng & Hou (2006); Zhang, Yue et al. (2005); Zhou et al. (2004). For related literature, see: Zhang et al. (2006).
3-Methoxysalicylaldehyde (0.2 mmol, 30.5 mg), cyclopropylamine (0.2 mmol, 11.5 mg), and cobalt(II) acetate tetrahydrate (0.1 mmol, 12.5 mg) were stirred at 318 K in methanol (20 ml) for 30 min. The filtrate was kept in air for twelve days depositing brown block-like crystals of (I).
All H-atoms bound to carbon were refined using a riding model with d(C—H) = 0.93–0.98 Å, and with Uiso = 1.2Ueq(C) and 1.5Ueq(methyl C).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL (Bruker, 2000); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).
Fig. 1. The molecular structure of (I), showing the atom-numbering scheme and 30% probability displacement ellipsoids. Unlabelled atoms are at the symmetry position -x, y, 1/2 - z. |
[Co(C11H12NO2)2] | F(000) = 916 |
Mr = 439.36 | Dx = 1.475 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 5017 reflections |
a = 20.249 (2) Å | θ = 2.4–28.1° |
b = 9.2011 (11) Å | µ = 0.90 mm−1 |
c = 13.1621 (16) Å | T = 298 K |
β = 126.193 (1)° | Block, brown |
V = 1979.1 (4) Å3 | 0.22 × 0.20 × 0.17 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 2254 independent reflections |
Radiation source: fine-focus sealed tube | 2078 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ω scans | θmax = 27.5°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −26→26 |
Tmin = 0.827, Tmax = 0.862 | k = −11→11 |
8175 measured reflections | l = −16→17 |
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)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.083 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0486P)2 + 0.7933P] where P = (Fo2 + 2Fc2)/3 |
2254 reflections | (Δ/σ)max < 0.001 |
133 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
[Co(C11H12NO2)2] | V = 1979.1 (4) Å3 |
Mr = 439.36 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 20.249 (2) Å | µ = 0.90 mm−1 |
b = 9.2011 (11) Å | T = 298 K |
c = 13.1621 (16) Å | 0.22 × 0.20 × 0.17 mm |
β = 126.193 (1)° |
Bruker SMART APEX CCD area-detector diffractometer | 2254 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 2078 reflections with I > 2σ(I) |
Tmin = 0.827, Tmax = 0.862 | Rint = 0.022 |
8175 measured reflections |
R[F2 > 2σ(F2)] = 0.030 | 0 restraints |
wR(F2) = 0.083 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.20 e Å−3 |
2254 reflections | Δρmin = −0.38 e Å−3 |
133 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 | 0.0000 | 0.71997 (3) | 0.2500 | 0.03157 (11) | |
O1 | 0.08279 (7) | 0.62869 (12) | 0.24704 (10) | 0.0369 (2) | |
O2 | 0.18014 (8) | 0.43298 (15) | 0.25833 (13) | 0.0550 (3) | |
N1 | −0.04711 (8) | 0.83432 (14) | 0.09181 (12) | 0.0331 (3) | |
C1 | 0.03581 (10) | 0.70545 (16) | 0.04006 (15) | 0.0334 (3) | |
C2 | 0.08396 (9) | 0.61938 (16) | 0.14909 (14) | 0.0317 (3) | |
C3 | 0.13761 (9) | 0.51622 (18) | 0.15175 (16) | 0.0385 (3) | |
C4 | 0.14302 (11) | 0.5045 (2) | 0.05247 (18) | 0.0471 (4) | |
H4 | 0.1786 | 0.4370 | 0.0564 | 0.056* | |
C5 | 0.09592 (12) | 0.5922 (2) | −0.05353 (18) | 0.0502 (5) | |
H5 | 0.1004 | 0.5840 | −0.1196 | 0.060* | |
C6 | 0.04346 (11) | 0.6897 (2) | −0.05995 (17) | 0.0441 (4) | |
H6 | 0.0118 | 0.7476 | −0.1313 | 0.053* | |
C7 | −0.02386 (10) | 0.80863 (17) | 0.02062 (15) | 0.0354 (3) | |
H7 | −0.0490 | 0.8640 | −0.0524 | 0.043* | |
C8 | −0.11140 (10) | 0.94043 (19) | 0.04572 (17) | 0.0437 (4) | |
H8 | −0.1237 | 0.9997 | −0.0254 | 0.052* | |
C9 | −0.12263 (12) | 1.0133 (2) | 0.1354 (2) | 0.0559 (5) | |
H9A | −0.0857 | 0.9869 | 0.2236 | 0.067* | |
H9B | −0.1398 | 1.1142 | 0.1197 | 0.067* | |
C10 | −0.18265 (11) | 0.9026 (2) | 0.0465 (2) | 0.0530 (5) | |
H10A | −0.2363 | 0.9362 | −0.0234 | 0.064* | |
H10B | −0.1822 | 0.8088 | 0.0805 | 0.064* | |
C11 | 0.23366 (14) | 0.3262 (3) | 0.2667 (2) | 0.0714 (7) | |
H11A | 0.2030 | 0.2592 | 0.1978 | 0.107* | |
H11B | 0.2595 | 0.2746 | 0.3448 | 0.107* | |
H11C | 0.2747 | 0.3725 | 0.2630 | 0.107* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.03802 (18) | 0.03337 (18) | 0.03506 (17) | 0.000 | 0.02805 (14) | 0.000 |
O1 | 0.0430 (6) | 0.0423 (6) | 0.0363 (6) | 0.0069 (5) | 0.0294 (5) | 0.0025 (4) |
O2 | 0.0552 (8) | 0.0550 (8) | 0.0609 (8) | 0.0187 (6) | 0.0376 (7) | 0.0023 (6) |
N1 | 0.0347 (6) | 0.0325 (6) | 0.0381 (6) | −0.0013 (5) | 0.0247 (6) | 0.0020 (5) |
C1 | 0.0379 (8) | 0.0366 (8) | 0.0352 (7) | −0.0103 (6) | 0.0269 (7) | −0.0070 (6) |
C2 | 0.0343 (7) | 0.0325 (7) | 0.0381 (7) | −0.0086 (6) | 0.0267 (6) | −0.0085 (6) |
C3 | 0.0371 (8) | 0.0377 (8) | 0.0485 (9) | −0.0051 (6) | 0.0295 (7) | −0.0101 (7) |
C4 | 0.0491 (9) | 0.0467 (9) | 0.0670 (11) | −0.0124 (8) | 0.0462 (9) | −0.0230 (8) |
C5 | 0.0647 (11) | 0.0569 (11) | 0.0550 (10) | −0.0191 (9) | 0.0497 (10) | −0.0207 (9) |
C6 | 0.0539 (10) | 0.0521 (10) | 0.0397 (9) | −0.0137 (8) | 0.0350 (8) | −0.0091 (7) |
C7 | 0.0393 (8) | 0.0369 (8) | 0.0339 (7) | −0.0061 (6) | 0.0237 (7) | 0.0016 (6) |
C8 | 0.0452 (9) | 0.0430 (9) | 0.0501 (9) | 0.0095 (7) | 0.0320 (8) | 0.0129 (7) |
C9 | 0.0592 (11) | 0.0492 (10) | 0.0672 (12) | 0.0154 (9) | 0.0417 (10) | 0.0035 (9) |
C10 | 0.0393 (9) | 0.0599 (11) | 0.0634 (11) | 0.0079 (8) | 0.0323 (9) | 0.0100 (9) |
C11 | 0.0540 (12) | 0.0672 (14) | 0.0746 (15) | 0.0223 (11) | 0.0278 (11) | −0.0132 (12) |
Co1—O1i | 1.8958 (10) | C5—C6 | 1.354 (3) |
Co1—O1 | 1.8958 (10) | C5—H5 | 0.9300 |
Co1—N1i | 2.0016 (13) | C6—H6 | 0.9300 |
Co1—N1 | 2.0016 (13) | C7—H7 | 0.9300 |
O1—C2 | 1.3063 (17) | C8—C9 | 1.487 (3) |
O2—C3 | 1.367 (2) | C8—C10 | 1.490 (2) |
O2—C11 | 1.418 (2) | C8—H8 | 0.9800 |
N1—C7 | 1.295 (2) | C9—C10 | 1.485 (3) |
N1—C8 | 1.443 (2) | C9—H9A | 0.9700 |
C1—C2 | 1.409 (2) | C9—H9B | 0.9700 |
C1—C6 | 1.421 (2) | C10—H10A | 0.9700 |
C1—C7 | 1.436 (2) | C10—H10B | 0.9700 |
C2—C3 | 1.427 (2) | C11—H11A | 0.9600 |
C3—C4 | 1.379 (2) | C11—H11B | 0.9600 |
C4—C5 | 1.392 (3) | C11—H11C | 0.9600 |
C4—H4 | 0.9300 | ||
O1i—Co1—O1 | 127.41 (7) | C1—C6—H6 | 119.3 |
O1i—Co1—N1i | 95.48 (5) | N1—C7—C1 | 128.25 (15) |
O1—Co1—N1i | 111.73 (5) | N1—C7—H7 | 115.9 |
O1i—Co1—N1 | 111.73 (5) | C1—C7—H7 | 115.9 |
O1—Co1—N1 | 95.48 (5) | N1—C8—C9 | 119.61 (15) |
N1i—Co1—N1 | 116.57 (8) | N1—C8—C10 | 118.42 (15) |
C2—O1—Co1 | 125.52 (10) | C9—C8—C10 | 59.83 (13) |
C3—O2—C11 | 117.19 (17) | N1—C8—H8 | 115.8 |
C7—N1—C8 | 116.26 (14) | C9—C8—H8 | 115.8 |
C7—N1—Co1 | 120.21 (11) | C10—C8—H8 | 115.8 |
C8—N1—Co1 | 123.39 (10) | C10—C9—C8 | 60.17 (13) |
C2—C1—C6 | 119.86 (15) | C10—C9—H9A | 117.8 |
C2—C1—C7 | 123.83 (14) | C8—C9—H9A | 117.8 |
C6—C1—C7 | 116.29 (16) | C10—C9—H9B | 117.8 |
O1—C2—C1 | 124.30 (13) | C8—C9—H9B | 117.8 |
O1—C2—C3 | 118.46 (14) | H9A—C9—H9B | 114.9 |
C1—C2—C3 | 117.24 (13) | C9—C10—C8 | 60.00 (13) |
O2—C3—C4 | 125.05 (15) | C9—C10—H10A | 117.8 |
O2—C3—C2 | 114.00 (14) | C8—C10—H10A | 117.8 |
C4—C3—C2 | 120.95 (16) | C9—C10—H10B | 117.8 |
C3—C4—C5 | 120.91 (16) | C8—C10—H10B | 117.8 |
C3—C4—H4 | 119.5 | H10A—C10—H10B | 114.9 |
C5—C4—H4 | 119.5 | O2—C11—H11A | 109.5 |
C6—C5—C4 | 119.66 (15) | O2—C11—H11B | 109.5 |
C6—C5—H5 | 120.2 | H11A—C11—H11B | 109.5 |
C4—C5—H5 | 120.2 | O2—C11—H11C | 109.5 |
C5—C6—C1 | 121.35 (18) | H11A—C11—H11C | 109.5 |
C5—C6—H6 | 119.3 | H11B—C11—H11C | 109.5 |
Symmetry code: (i) −x, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Co(C11H12NO2)2] |
Mr | 439.36 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 298 |
a, b, c (Å) | 20.249 (2), 9.2011 (11), 13.1621 (16) |
β (°) | 126.193 (1) |
V (Å3) | 1979.1 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.90 |
Crystal size (mm) | 0.22 × 0.20 × 0.17 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.827, 0.862 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8175, 2254, 2078 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.030, 0.083, 1.09 |
No. of reflections | 2254 |
No. of parameters | 133 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.38 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Bruker, 2000).
Co1—O1 | 1.8958 (10) | Co1—N1 | 2.0016 (13) |
O1i—Co1—O1 | 127.41 (7) | O1—Co1—N1 | 95.48 (5) |
O1i—Co1—N1 | 111.73 (5) | N1i—Co1—N1 | 116.57 (8) |
Symmetry code: (i) −x, y, −z+1/2. |
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The design of O/N-donor multidentate ligands, their metallosupramolecular chemistry and the study of their physical properties have been of considerable recent interest (Robin & Fromm, 2006; Vicente & Arcas, 2005; Au-Yeung & Chan, 2004). A major goal in modern coordination chemistry is to synthesize molecules with a predefined geometry. Condensation of aromatic carbaldehydes with primary amines offers an easy and inexpensive way of forming a variety of polydentate Schiff base ligands, leading to the formation of a variety of complexes (Lewiński et al., 2005; Salmon et al., 2005; Xu et al., 2005; Liu et al., 2006). We report here the synthesis and structure of the title mononuclear cobalt(II) complex (I), Fig. 1, Table 1.
The CoII atom in (I), lying on a twofold rotation axis, is four-coordinated by two imine N and two phenolate O atoms from two Schiff base ligand, forming a distorted tetrahedral coordination geometry. The metal-ligand bond lengths are comparable to the values in other similar cobalt(II) complexes (Zhou et al., 2004; Iyere et al., 2004; Zhang et al., 2006; Yue et al., 2005; Peng & Hou, 2006).