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The title compound, [Co(C13H15N2O3)2], is isostructural with the zinc(II) compound reported previously. The Co atom is coordinated by four donor atoms from two Schiff base ligands, forming a tetra­hedral geometry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805042182/su6260sup1.cif
Contains datablocks crystal, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805042182/su6260Isup2.hkl
Contains datablock I

CCDC reference: 296682

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C)= 0.003 Å
  • R factor = 0.038
  • wR factor = 0.104
  • Data-to-parameter ratio = 17.5

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Comment top

Cobalt compounds are of great interest in coordination chemistry (Billson et al., 2000; Kotera et al., 2003; Fritsky et al., 2003). As part of our investigations on non-covalent interactions in metal complexes (Chen, 2005), the new title CoII complex, (I), has been prepared and its crystal structure is presented here.

Complex (I) is a mononuclear cobalt(II) compound (Fig. 1), which is isostructural with the zinc compound bis[2-(cyclohexyliminomethyl)-4-nitrophenolato]zinc(II) (You, 2005), and structurally similar with the cobalt compound bis[4-chloro-2-(cyclohexyliminomethyl)phenolato]cobalt(II) (Li & Zhang, 2005). In (I), the Co atom is coordinated by four donor atoms from two Schiff base ligands, forming a tetrahedral geometry. The Schiff base acts as a bidentate ligand and ligates to the metal via the phenolate O and imine N atoms. All the bond lengths (Table 1) around the metal center are comparable to those in similar complexes (Fun et al., 1999; Iyere et al., 2004; Elerman et al., 1996).

Experimental top

All the chemicals were of AR grade. 5-Nitro-2-hydroxybenzaldehyde (16.7 mg, 0.1 mmol), cyclohexylamine (9.9 mg, 0.1 mmol) and CoCl2·4H2O (20.2 mg, 0.1 mmol) were refluxed in 30 ml MeOH for 30 min. The mixture was cooled to room temperature and filtered. After keeping the filtrate in air for 11 d, red block crystals suitable for X-ray analysis were obtained.

Refinement top

All the H atoms were positioned geometrically and refined as riding atoms, with C—H distances of 0.93–0.98 Å and Uiso(H) = 1.2Ueq(parent C-atom).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of compound (I), showing the labelling scheme and displacement ellipsoids drawn at the 30% probability level.
(I) top
Crystal data top
[Co(C13H15N2O3)2]Z = 2
Mr = 553.47F(000) = 578
Triclinic, P1Dx = 1.423 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.765 (1) ÅCell parameters from 5677 reflections
b = 11.135 (1) Åθ = 2.3–27.4°
c = 12.410 (1) ŵ = 0.71 mm1
α = 113.698 (1)°T = 298 K
β = 104.064 (1)°Block, red
γ = 95.105 (1)°0.20 × 0.16 × 0.10 mm
V = 1291.84 (19) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
5834 independent reflections
Radiation source: fine-focus sealed tube4950 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ϕ and ω scansθmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1313
Tmin = 0.871, Tmax = 0.932k = 1414
15016 measured reflectionsl = 1516
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0538P)2 + 0.2812P]
where P = (Fo2 + 2Fc2)/3
5834 reflections(Δ/σ)max < 0.001
334 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
[Co(C13H15N2O3)2]γ = 95.105 (1)°
Mr = 553.47V = 1291.84 (19) Å3
Triclinic, P1Z = 2
a = 10.765 (1) ÅMo Kα radiation
b = 11.135 (1) ŵ = 0.71 mm1
c = 12.410 (1) ÅT = 298 K
α = 113.698 (1)°0.20 × 0.16 × 0.10 mm
β = 104.064 (1)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
5834 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
4950 reflections with I > 2σ(I)
Tmin = 0.871, Tmax = 0.932Rint = 0.022
15016 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.104H-atom parameters constrained
S = 1.03Δρmax = 0.27 e Å3
5834 reflectionsΔρmin = 0.22 e Å3
334 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Co10.96670 (2)0.79077 (2)0.59431 (2)0.04198 (10)
O10.85602 (13)0.66690 (13)0.43260 (12)0.0486 (3)
O20.32733 (16)0.61265 (19)0.05856 (16)0.0782 (5)
O30.35281 (15)0.81668 (19)0.19317 (17)0.0745 (5)
O41.14781 (13)0.85335 (15)0.62309 (13)0.0518 (3)
O51.56691 (16)0.7751 (2)1.02264 (17)0.0750 (5)
O61.68770 (14)0.89811 (18)0.97386 (17)0.0733 (5)
N10.86357 (15)0.93420 (15)0.61478 (13)0.0407 (3)
N20.38829 (16)0.7098 (2)0.15649 (17)0.0549 (4)
N30.99439 (14)0.70069 (15)0.70580 (13)0.0388 (3)
N41.58130 (16)0.83807 (18)0.96389 (17)0.0540 (4)
C10.74658 (18)0.68143 (18)0.37277 (16)0.0405 (4)
C20.69371 (17)0.79898 (18)0.41709 (16)0.0392 (4)
C30.57429 (18)0.80323 (19)0.34325 (17)0.0433 (4)
H30.53870.87890.37130.052*
C40.50920 (18)0.6983 (2)0.23083 (17)0.0440 (4)
C50.5580 (2)0.5827 (2)0.18681 (18)0.0501 (5)
H50.51270.51150.11060.060*
C60.6731 (2)0.5754 (2)0.25696 (18)0.0512 (5)
H60.70480.49730.22750.061*
C70.75592 (18)0.91578 (18)0.53224 (17)0.0426 (4)
H70.71280.98680.54900.051*
C80.90651 (19)1.06745 (18)0.72353 (16)0.0440 (4)
H80.82821.10340.73420.053*
C90.9936 (3)1.1635 (2)0.7021 (2)0.0605 (6)
H9A0.94741.17180.62870.073*
H9B1.07111.12930.68880.073*
C101.0340 (3)1.3015 (2)0.8141 (2)0.0670 (6)
H10A1.09441.36100.80150.080*
H10B0.95721.33960.82150.080*
C111.0984 (2)1.2923 (2)0.9321 (2)0.0668 (6)
H11A1.18141.26570.92930.080*
H11B1.11601.37971.00160.080*
C121.0129 (3)1.1926 (2)0.9504 (2)0.0703 (7)
H12A0.93511.22550.96450.084*
H12B1.05991.18371.02320.084*
C130.9724 (3)1.0554 (2)0.83917 (19)0.0634 (6)
H13A1.04911.01760.83030.076*
H13B0.91290.99550.85200.076*
C141.23186 (17)0.78238 (17)0.78096 (16)0.0386 (4)
C151.24520 (18)0.84666 (18)0.70432 (17)0.0434 (4)
C161.3732 (2)0.9053 (2)0.7178 (2)0.0579 (5)
H161.38410.94640.66770.069*
C171.4815 (2)0.9039 (2)0.8013 (2)0.0562 (5)
H171.56450.94410.80850.067*
C181.46565 (18)0.84157 (18)0.87529 (18)0.0446 (4)
C191.34494 (17)0.78290 (18)0.86681 (17)0.0417 (4)
H191.33710.74270.91830.050*
C201.10951 (17)0.71205 (18)0.77479 (16)0.0394 (4)
H201.11430.67000.82660.047*
C210.88472 (17)0.61355 (18)0.70900 (16)0.0398 (4)
H210.90950.60910.78850.048*
C220.76253 (18)0.6725 (2)0.69888 (19)0.0478 (4)
H22A0.77980.75970.76860.057*
H22B0.74090.68490.62390.057*
C230.64722 (19)0.5813 (2)0.6966 (2)0.0540 (5)
H23A0.66530.57600.77490.065*
H23B0.56960.61870.68570.065*
C240.62213 (19)0.4422 (2)0.5927 (2)0.0543 (5)
H24A0.59790.44660.51400.065*
H24B0.54990.38490.59420.065*
C250.7435 (2)0.3829 (2)0.6057 (2)0.0558 (5)
H25A0.72640.29450.53770.067*
H25B0.76450.37340.68210.067*
C260.85958 (19)0.47217 (19)0.60622 (19)0.0486 (4)
H26A0.84180.47540.52710.058*
H26B0.93700.43480.61830.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.03937 (15)0.04773 (16)0.03899 (15)0.01415 (11)0.00682 (10)0.02107 (12)
O10.0484 (7)0.0497 (7)0.0413 (7)0.0202 (6)0.0059 (6)0.0161 (6)
O20.0563 (10)0.0854 (12)0.0633 (11)0.0018 (9)0.0140 (8)0.0255 (9)
O30.0473 (9)0.0888 (13)0.0807 (12)0.0265 (9)0.0061 (8)0.0361 (10)
O40.0425 (7)0.0650 (9)0.0548 (8)0.0105 (6)0.0079 (6)0.0371 (7)
O50.0510 (9)0.1031 (14)0.0776 (12)0.0198 (9)0.0035 (8)0.0545 (11)
O60.0358 (8)0.0792 (11)0.0885 (12)0.0064 (7)0.0020 (8)0.0319 (10)
N10.0422 (8)0.0425 (8)0.0341 (7)0.0113 (6)0.0085 (6)0.0150 (6)
N20.0382 (9)0.0702 (12)0.0546 (10)0.0053 (8)0.0056 (8)0.0318 (9)
N30.0353 (7)0.0427 (8)0.0373 (7)0.0098 (6)0.0093 (6)0.0173 (6)
N40.0370 (9)0.0545 (10)0.0544 (10)0.0121 (7)0.0031 (7)0.0140 (8)
C10.0426 (9)0.0424 (9)0.0365 (9)0.0110 (7)0.0099 (7)0.0180 (8)
C20.0392 (9)0.0399 (9)0.0364 (9)0.0083 (7)0.0077 (7)0.0170 (7)
C30.0401 (9)0.0449 (10)0.0461 (10)0.0120 (8)0.0105 (8)0.0221 (8)
C40.0375 (9)0.0518 (11)0.0421 (10)0.0035 (8)0.0057 (8)0.0247 (9)
C50.0506 (11)0.0491 (11)0.0375 (10)0.0036 (9)0.0049 (8)0.0125 (8)
C60.0546 (12)0.0448 (10)0.0449 (11)0.0146 (9)0.0101 (9)0.0126 (9)
C70.0445 (10)0.0407 (9)0.0405 (9)0.0136 (8)0.0106 (8)0.0163 (8)
C80.0437 (10)0.0432 (10)0.0361 (9)0.0120 (8)0.0085 (8)0.0100 (8)
C90.0772 (15)0.0509 (12)0.0472 (11)0.0055 (11)0.0163 (11)0.0189 (10)
C100.0839 (17)0.0461 (12)0.0584 (14)0.0015 (11)0.0138 (12)0.0177 (10)
C110.0566 (13)0.0552 (13)0.0581 (13)0.0060 (10)0.0035 (10)0.0085 (11)
C120.0975 (19)0.0607 (14)0.0335 (10)0.0089 (13)0.0041 (11)0.0126 (10)
C130.0905 (17)0.0506 (12)0.0386 (11)0.0042 (11)0.0075 (11)0.0183 (9)
C140.0362 (9)0.0374 (9)0.0378 (9)0.0092 (7)0.0079 (7)0.0137 (7)
C150.0407 (9)0.0428 (10)0.0435 (10)0.0090 (8)0.0081 (8)0.0184 (8)
C160.0490 (11)0.0638 (13)0.0660 (14)0.0014 (10)0.0112 (10)0.0393 (12)
C170.0389 (10)0.0554 (12)0.0679 (14)0.0005 (9)0.0101 (9)0.0263 (11)
C180.0362 (9)0.0404 (9)0.0444 (10)0.0090 (7)0.0030 (8)0.0113 (8)
C190.0399 (9)0.0401 (9)0.0394 (9)0.0103 (7)0.0061 (7)0.0150 (8)
C200.0402 (9)0.0421 (9)0.0365 (9)0.0115 (7)0.0102 (7)0.0182 (8)
C210.0363 (9)0.0459 (10)0.0360 (9)0.0077 (7)0.0082 (7)0.0187 (8)
C220.0410 (10)0.0507 (11)0.0502 (11)0.0131 (8)0.0155 (8)0.0193 (9)
C230.0381 (10)0.0680 (13)0.0566 (12)0.0117 (9)0.0166 (9)0.0266 (11)
C240.0391 (10)0.0646 (13)0.0526 (12)0.0010 (9)0.0070 (9)0.0258 (10)
C250.0533 (12)0.0482 (11)0.0607 (13)0.0053 (9)0.0145 (10)0.0214 (10)
C260.0451 (10)0.0482 (11)0.0525 (11)0.0133 (8)0.0164 (9)0.0204 (9)
Geometric parameters (Å, º) top
Co1—O41.906 (2)C11—C121.501 (4)
Co1—O11.916 (2)C11—H11A0.9700
Co1—N11.994 (2)C11—H11B0.9700
Co1—N31.994 (2)C12—C131.524 (3)
O1—C11.293 (2)C12—H12A0.9700
O2—N21.228 (2)C12—H12B0.9700
O3—N21.224 (2)C13—H13A0.9700
O4—C151.297 (2)C13—H13B0.9700
O5—N41.222 (2)C14—C191.407 (2)
O6—N41.226 (2)C14—C151.426 (3)
N1—C71.283 (2)C14—C201.440 (2)
N1—C81.484 (2)C15—C161.412 (3)
N2—C41.450 (2)C16—C171.365 (3)
N3—C201.286 (2)C16—H160.9300
N3—C211.479 (2)C17—C181.386 (3)
N4—C181.462 (2)C17—H170.9300
C1—C61.415 (3)C18—C191.362 (3)
C1—C21.430 (2)C19—H190.9300
C2—C31.403 (2)C20—H200.9300
C2—C71.438 (2)C21—C221.522 (3)
C3—C41.368 (3)C21—C261.523 (3)
C3—H30.9300C21—H210.9800
C4—C51.387 (3)C22—C231.520 (3)
C5—C61.361 (3)C22—H22A0.9700
C5—H50.9300C22—H22B0.9700
C6—H60.9300C23—C241.512 (3)
C7—H70.9300C23—H23A0.9700
C8—C131.502 (3)C23—H23B0.9700
C8—C91.506 (3)C24—C251.519 (3)
C8—H80.9800C24—H24A0.9700
C9—C101.534 (3)C24—H24B0.9700
C9—H9A0.9700C25—C261.523 (3)
C9—H9B0.9700C25—H25A0.9700
C10—C111.508 (3)C25—H25B0.9700
C10—H10A0.9700C26—H26A0.9700
C10—H10B0.9700C26—H26B0.9700
O4—Co1—O1120.86 (6)C13—C12—H12A109.2
O4—Co1—N1113.14 (6)C11—C12—H12B109.2
O1—Co1—N195.95 (6)C13—C12—H12B109.2
O4—Co1—N395.93 (6)H12A—C12—H12B107.9
O1—Co1—N3110.11 (6)C8—C13—C12110.42 (19)
N1—Co1—N3122.81 (6)C8—C13—H13A109.6
C1—O1—Co1126.49 (12)C12—C13—H13A109.6
C15—O4—Co1126.20 (12)C8—C13—H13B109.6
C7—N1—C8116.31 (15)C12—C13—H13B109.6
C7—N1—Co1120.99 (12)H13A—C13—H13B108.1
C8—N1—Co1122.70 (11)C19—C14—C15118.97 (17)
O3—N2—O2122.99 (19)C19—C14—C20116.53 (16)
O3—N2—C4118.53 (18)C15—C14—C20124.47 (16)
O2—N2—C4118.47 (19)O4—C15—C16118.48 (18)
C20—N3—C21117.09 (15)O4—C15—C14124.18 (17)
C20—N3—Co1121.24 (13)C16—C15—C14117.33 (17)
C21—N3—Co1121.62 (11)C17—C16—C15122.6 (2)
O5—N4—O6123.86 (18)C17—C16—H16118.7
O5—N4—C18118.59 (17)C15—C16—H16118.7
O6—N4—C18117.55 (19)C16—C17—C18118.85 (18)
O1—C1—C6118.85 (17)C16—C17—H17120.6
O1—C1—C2123.81 (16)C18—C17—H17120.6
C6—C1—C2117.33 (16)C19—C18—C17121.48 (18)
C3—C2—C1118.53 (16)C19—C18—N4119.30 (18)
C3—C2—C7116.99 (16)C17—C18—N4119.22 (18)
C1—C2—C7124.47 (16)C18—C19—C14120.73 (18)
C4—C3—C2121.32 (17)C18—C19—H19119.6
C4—C3—H3119.3C14—C19—H19119.6
C2—C3—H3119.3N3—C20—C14127.42 (17)
C3—C4—C5121.05 (17)N3—C20—H20116.3
C3—C4—N2119.02 (18)C14—C20—H20116.3
C5—C4—N2119.92 (18)N3—C21—C22110.36 (15)
C6—C5—C4118.89 (18)N3—C21—C26110.04 (14)
C6—C5—H5120.6C22—C21—C26111.37 (15)
C4—C5—H5120.6N3—C21—H21108.3
C5—C6—C1122.85 (18)C22—C21—H21108.3
C5—C6—H6118.6C26—C21—H21108.3
C1—C6—H6118.6C23—C22—C21111.09 (17)
N1—C7—C2128.08 (17)C23—C22—H22A109.4
N1—C7—H7116.0C21—C22—H22A109.4
C2—C7—H7116.0C23—C22—H22B109.4
N1—C8—C13111.06 (16)C21—C22—H22B109.4
N1—C8—C9110.83 (15)H22A—C22—H22B108.0
C13—C8—C9111.50 (18)C24—C23—C22110.79 (17)
N1—C8—H8107.8C24—C23—H23A109.5
C13—C8—H8107.8C22—C23—H23A109.5
C9—C8—H8107.8C24—C23—H23B109.5
C8—C9—C10110.01 (18)C22—C23—H23B109.5
C8—C9—H9A109.7H23A—C23—H23B108.1
C10—C9—H9A109.7C23—C24—C25110.51 (17)
C8—C9—H9B109.7C23—C24—H24A109.5
C10—C9—H9B109.7C25—C24—H24A109.5
H9A—C9—H9B108.2C23—C24—H24B109.5
C11—C10—C9111.6 (2)C25—C24—H24B109.5
C11—C10—H10A109.3H24A—C24—H24B108.1
C9—C10—H10A109.3C24—C25—C26110.81 (17)
C11—C10—H10B109.3C24—C25—H25A109.5
C9—C10—H10B109.3C26—C25—H25A109.5
H10A—C10—H10B108.0C24—C25—H25B109.5
C12—C11—C10111.30 (19)C26—C25—H25B109.5
C12—C11—H11A109.4H25A—C25—H25B108.1
C10—C11—H11A109.4C25—C26—C21110.45 (16)
C12—C11—H11B109.4C25—C26—H26A109.6
C10—C11—H11B109.4C21—C26—H26A109.6
H11A—C11—H11B108.0C25—C26—H26B109.6
C11—C12—C13111.9 (2)C21—C26—H26B109.6
C11—C12—H12A109.2H26A—C26—H26B108.1

Experimental details

Crystal data
Chemical formula[Co(C13H15N2O3)2]
Mr553.47
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)10.765 (1), 11.135 (1), 12.410 (1)
α, β, γ (°)113.698 (1), 104.064 (1), 95.105 (1)
V3)1291.84 (19)
Z2
Radiation typeMo Kα
µ (mm1)0.71
Crystal size (mm)0.20 × 0.16 × 0.10
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.871, 0.932
No. of measured, independent and
observed [I > 2σ(I)] reflections
15016, 5834, 4950
Rint0.022
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.104, 1.03
No. of reflections5834
No. of parameters334
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.27, 0.22

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

Selected geometric parameters (Å, º) top
Co1—O41.906 (2)Co1—N11.994 (2)
Co1—O11.916 (2)Co1—N31.994 (2)
O4—Co1—O1120.86 (6)O4—Co1—N395.93 (6)
O4—Co1—N1113.14 (6)O1—Co1—N3110.11 (6)
O1—Co1—N195.95 (6)N1—Co1—N3122.81 (6)
 

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