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In the title compound, [Co(C11H12NO2)2], the CoII atom, lying on a twofold rotation axis, is four-coordinated by two imine N and two phenolate O atoms from two Schiff base ligands in a distorted tetra­hedral coordination gometry. The two Schiff base ligands are nearly perpendicular to each other, with a dihedral angle of 87.1 (2)° between their mean planes.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807061880/sj2429sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807061880/sj2429Isup2.hkl
Contains datablock I

CCDC reference: 672769

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C)= 0.003 Å
  • R factor = 0.030
  • wR factor = 0.083
  • Data-to-parameter ratio = 16.9

checkCIF/PLATON results

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Comment top

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).

Related literature top

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).

Experimental top

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).

Refinement top

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).

Computing details top

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).

Figures top
[Figure 1] 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.
Bis[2-(cyclopropyliminomethyl)-6-methoxyphenolato]cobalt(II) top
Crystal data top
[Co(C11H12NO2)2]F(000) = 916
Mr = 439.36Dx = 1.475 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 5017 reflections
a = 20.249 (2) Åθ = 2.4–28.1°
b = 9.2011 (11) ŵ = 0.90 mm1
c = 13.1621 (16) ÅT = 298 K
β = 126.193 (1)°Block, brown
V = 1979.1 (4) Å30.22 × 0.20 × 0.17 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2254 independent reflections
Radiation source: fine-focus sealed tube2078 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ω scansθmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 2626
Tmin = 0.827, Tmax = 0.862k = 1111
8175 measured reflectionsl = 1617
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083H-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 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.38 e Å3
Crystal data top
[Co(C11H12NO2)2]V = 1979.1 (4) Å3
Mr = 439.36Z = 4
Monoclinic, C2/cMo Kα radiation
a = 20.249 (2) ŵ = 0.90 mm1
b = 9.2011 (11) ÅT = 298 K
c = 13.1621 (16) Å0.22 × 0.20 × 0.17 mm
β = 126.193 (1)°
Data collection top
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 = 0.862Rint = 0.022
8175 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.083H-atom parameters constrained
S = 1.09Δρmax = 0.20 e Å3
2254 reflectionsΔρmin = 0.38 e Å3
133 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Co10.00000.71997 (3)0.25000.03157 (11)
O10.08279 (7)0.62869 (12)0.24704 (10)0.0369 (2)
O20.18014 (8)0.43298 (15)0.25833 (13)0.0550 (3)
N10.04711 (8)0.83432 (14)0.09181 (12)0.0331 (3)
C10.03581 (10)0.70545 (16)0.04006 (15)0.0334 (3)
C20.08396 (9)0.61938 (16)0.14909 (14)0.0317 (3)
C30.13761 (9)0.51622 (18)0.15175 (16)0.0385 (3)
C40.14302 (11)0.5045 (2)0.05247 (18)0.0471 (4)
H40.17860.43700.05640.056*
C50.09592 (12)0.5922 (2)0.05353 (18)0.0502 (5)
H50.10040.58400.11960.060*
C60.04346 (11)0.6897 (2)0.05995 (17)0.0441 (4)
H60.01180.74760.13130.053*
C70.02386 (10)0.80863 (17)0.02062 (15)0.0354 (3)
H70.04900.86400.05240.043*
C80.11140 (10)0.94043 (19)0.04572 (17)0.0437 (4)
H80.12370.99970.02540.052*
C90.12263 (12)1.0133 (2)0.1354 (2)0.0559 (5)
H9A0.08570.98690.22360.067*
H9B0.13981.11420.11970.067*
C100.18265 (11)0.9026 (2)0.0465 (2)0.0530 (5)
H10A0.23630.93620.02340.064*
H10B0.18220.80880.08050.064*
C110.23366 (14)0.3262 (3)0.2667 (2)0.0714 (7)
H11A0.20300.25920.19780.107*
H11B0.25950.27460.34480.107*
H11C0.27470.37250.26300.107*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.03802 (18)0.03337 (18)0.03506 (17)0.0000.02805 (14)0.000
O10.0430 (6)0.0423 (6)0.0363 (6)0.0069 (5)0.0294 (5)0.0025 (4)
O20.0552 (8)0.0550 (8)0.0609 (8)0.0187 (6)0.0376 (7)0.0023 (6)
N10.0347 (6)0.0325 (6)0.0381 (6)0.0013 (5)0.0247 (6)0.0020 (5)
C10.0379 (8)0.0366 (8)0.0352 (7)0.0103 (6)0.0269 (7)0.0070 (6)
C20.0343 (7)0.0325 (7)0.0381 (7)0.0086 (6)0.0267 (6)0.0085 (6)
C30.0371 (8)0.0377 (8)0.0485 (9)0.0051 (6)0.0295 (7)0.0101 (7)
C40.0491 (9)0.0467 (9)0.0670 (11)0.0124 (8)0.0462 (9)0.0230 (8)
C50.0647 (11)0.0569 (11)0.0550 (10)0.0191 (9)0.0497 (10)0.0207 (9)
C60.0539 (10)0.0521 (10)0.0397 (9)0.0137 (8)0.0350 (8)0.0091 (7)
C70.0393 (8)0.0369 (8)0.0339 (7)0.0061 (6)0.0237 (7)0.0016 (6)
C80.0452 (9)0.0430 (9)0.0501 (9)0.0095 (7)0.0320 (8)0.0129 (7)
C90.0592 (11)0.0492 (10)0.0672 (12)0.0154 (9)0.0417 (10)0.0035 (9)
C100.0393 (9)0.0599 (11)0.0634 (11)0.0079 (8)0.0323 (9)0.0100 (9)
C110.0540 (12)0.0672 (14)0.0746 (15)0.0223 (11)0.0278 (11)0.0132 (12)
Geometric parameters (Å, º) top
Co1—O1i1.8958 (10)C5—C61.354 (3)
Co1—O11.8958 (10)C5—H50.9300
Co1—N1i2.0016 (13)C6—H60.9300
Co1—N12.0016 (13)C7—H70.9300
O1—C21.3063 (17)C8—C91.487 (3)
O2—C31.367 (2)C8—C101.490 (2)
O2—C111.418 (2)C8—H80.9800
N1—C71.295 (2)C9—C101.485 (3)
N1—C81.443 (2)C9—H9A0.9700
C1—C21.409 (2)C9—H9B0.9700
C1—C61.421 (2)C10—H10A0.9700
C1—C71.436 (2)C10—H10B0.9700
C2—C31.427 (2)C11—H11A0.9600
C3—C41.379 (2)C11—H11B0.9600
C4—C51.392 (3)C11—H11C0.9600
C4—H40.9300
O1i—Co1—O1127.41 (7)C1—C6—H6119.3
O1i—Co1—N1i95.48 (5)N1—C7—C1128.25 (15)
O1—Co1—N1i111.73 (5)N1—C7—H7115.9
O1i—Co1—N1111.73 (5)C1—C7—H7115.9
O1—Co1—N195.48 (5)N1—C8—C9119.61 (15)
N1i—Co1—N1116.57 (8)N1—C8—C10118.42 (15)
C2—O1—Co1125.52 (10)C9—C8—C1059.83 (13)
C3—O2—C11117.19 (17)N1—C8—H8115.8
C7—N1—C8116.26 (14)C9—C8—H8115.8
C7—N1—Co1120.21 (11)C10—C8—H8115.8
C8—N1—Co1123.39 (10)C10—C9—C860.17 (13)
C2—C1—C6119.86 (15)C10—C9—H9A117.8
C2—C1—C7123.83 (14)C8—C9—H9A117.8
C6—C1—C7116.29 (16)C10—C9—H9B117.8
O1—C2—C1124.30 (13)C8—C9—H9B117.8
O1—C2—C3118.46 (14)H9A—C9—H9B114.9
C1—C2—C3117.24 (13)C9—C10—C860.00 (13)
O2—C3—C4125.05 (15)C9—C10—H10A117.8
O2—C3—C2114.00 (14)C8—C10—H10A117.8
C4—C3—C2120.95 (16)C9—C10—H10B117.8
C3—C4—C5120.91 (16)C8—C10—H10B117.8
C3—C4—H4119.5H10A—C10—H10B114.9
C5—C4—H4119.5O2—C11—H11A109.5
C6—C5—C4119.66 (15)O2—C11—H11B109.5
C6—C5—H5120.2H11A—C11—H11B109.5
C4—C5—H5120.2O2—C11—H11C109.5
C5—C6—C1121.35 (18)H11A—C11—H11C109.5
C5—C6—H6119.3H11B—C11—H11C109.5
Symmetry code: (i) x, y, z+1/2.

Experimental details

Crystal data
Chemical formula[Co(C11H12NO2)2]
Mr439.36
Crystal system, space groupMonoclinic, C2/c
Temperature (K)298
a, b, c (Å)20.249 (2), 9.2011 (11), 13.1621 (16)
β (°) 126.193 (1)
V3)1979.1 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.90
Crystal size (mm)0.22 × 0.20 × 0.17
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.827, 0.862
No. of measured, independent and
observed [I > 2σ(I)] reflections
8175, 2254, 2078
Rint0.022
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.083, 1.09
No. of reflections2254
No. of parameters133
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.38

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Bruker, 2000).

Selected geometric parameters (Å, º) top
Co1—O11.8958 (10)Co1—N12.0016 (13)
O1i—Co1—O1127.41 (7)O1—Co1—N195.48 (5)
O1i—Co1—N1111.73 (5)N1i—Co1—N1116.57 (8)
Symmetry code: (i) x, y, z+1/2.
 

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