Bis(1H-pyrazole-κN2)bis­(2,4,6-tri­isopropyl­benzoato-κO)cobalt(II)

Hrib, C.G.; Blaurock, S.; Edelmann, F.T.

doi:10.1107/S1600536810039553

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page m1387

https://doi.org/10.1107/S1600536810039553

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Bis(1H-pyrazole-κN²)bis(2,4,6-triisopropylbenzoato-κO)cobalt(II)

Cristian G. Hrib,^a Steffen Blaurock ^a and Frank T. Edelmann ^a ^*

^aChemisches Institut der Otto-von-Guericke-Universität, Universitätsplatz 2, D-39116 Magdeburg, Germany
^*Correspondence e-mail: frank.edelmann@ovgu.de

(Received 22 September 2010; accepted 4 October 2010; online 13 October 2010)

The title compound, [Co(C₁₆H₂₃O₂)₂(C₃H₄N₂)₂] or (C₃H₄N₂)₂Co(O₂CC₆H₂ⁱPr₃-2,4,6), is a rare example of a tetracoordinate cobalt(II) carboxylate stabilized by ancillary N-heterocyclic ligands. The Co(II) ion resides on a crystallographic twofold axis so that the asymmetric unit comprises one half-molecule. Due to the steric bulk of the 2,4,6-triisopropylphenyl substituents, the carboxylate ligands are both coordinated in a monodentate fashion despite the low coordination number. The coordination geometry around the central Co(II) ion is distorted tetrahedral with angles at Co ranging from 92.27 (18)° to 121.08 (14)°.

Related literature

For cobalt(II) carboxylate complexes containing N-coordinated heterocyclic ligands, see: Manhas et al. (1975 ); Catterick & Thornton (1976 ); Kumar & Gandotra (1980a ,b ); Kumar & Bajju (1999 ); Ju et al. (2006 ); Karmakar et al. (2007 ). Normally the carboxylate anions are either bidentate or bridging. For an exception in which the benzoate ligands are coordinated in a monodentate fashion, see: Hökelek & Necefouğlu (1999 ). Interesting supramolecular structures have also been reported, see: Boldog et al. (2001 ).

Experimental

Crystal data

[Co(C₁₆H₂₃O₂)₂(C₃H₄N₂)₂]
M_r = 689.78
Orthorhombic, P b c n
a = 9.6146 (19) Å
b = 12.792 (3) Å
c = 31.275 (6) Å
V = 3846.5 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.49 mm⁻¹
T = 153 K
0.80 × 0.50 × 0.10 mm

Data collection

Stoe STADI4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.696, T_max = 0.953
6256 measured reflections
3378 independent reflections
2073 reflections with I > 2σ(I)
R_int = 0.071
3 standard reflections every 120 min intensity decay: 3%

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.173
S = 1.09
3378 reflections
213 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Data collection: DIF4 (Stoe & Cie, 1992 ); cell refinement: DIF4; data reduction: REDU4 (Stoe & Cie, 1992); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S1600536810039553/fj2344sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810039553/fj2344Isup2.hkl

checkCIF report

Comment top

Cobalt(II) carboxylate complexes containing N-coordinated heterocyclic ligands have been the subject of detailed structural investigations in the past [Manhas et al. (1975); Catterick et al. (1976); Kumar et al. (1980a,b, 1999); Ju et al. (2006); Karmakar et al. (2007)]. The most frequently employed co-ligands are pyridine derivatives. Normally the carboxylate anions are either bidentate or bridging. A notable exception is the octahedral complex trans-diaqua-bis(benzoato-O)-bis(nicotinamide-N1)cobalt(II), in which the benzoate ligands are coordinated in a monodentate fashion [Hökelek et al. (1999)]. Interesting supramolecular structures have have also been reported in this chemistry [Boldog et al. (2001)]. These compounds contained the heterocyclic co-ligand 3,3',5,5'-tetramethyl-4,4'-bipyrazolyl. The title compound, which contains unsubstituted pyrazole as co-ligand, was obtained in small amounts from a reaction of cobalt(II) hydroxide with 2,4,6-triisopropylbenzoic acid in aqueous solution in the presence of pyrazole. The coordination geometry around the central cobalt atom is distorted tetrahedral. Due to the steric bulk of the 2,4,6-triisopropylphenyl substituents the carboxylate ligands in the title compound are monodentate despite the low coordination number of 4 around Co.

Related literature top

For cobalt(II) carboxylate complexes containing N-coordinated heterocyclic ligands, see: Manhas et al. (1975); Catterick & Thornton (1976); Kumar & Gandotra (1980a,b); Kumar & Bajju (1999); Ju et al. (2006); Karmakar et al. (2007). Normally the carboxylate anions are either bidentate or bridging. For an exception in which the benzoate ligands are coordinated in a monodentate fashion, see: Hökelek & Necefouğlu (1999). Interesting supramolecular structures have have also been reported, see: Boldog et al. (2001).

Experimental top

Small amounts of blue single crystals of the title compound were obtained from a reaction of cobalt(II) hydroxide with 2,4,6-triisopropylbenzoic acid in aqueous solution in the presence of pyrazole.

Structure description top

For cobalt(II) carboxylate complexes containing N-coordinated heterocyclic ligands, see: Manhas et al. (1975); Catterick & Thornton (1976); Kumar & Gandotra (1980a,b); Kumar & Bajju (1999); Ju et al. (2006); Karmakar et al. (2007). Normally the carboxylate anions are either bidentate or bridging. For an exception in which the benzoate ligands are coordinated in a monodentate fashion, see: Hökelek & Necefouğlu (1999). Interesting supramolecular structures have have also been reported, see: Boldog et al. (2001).

Computing details top

Data collection: DIF4 (Stoe & Cie, 1992); cell refinement: DIF4 (Stoe & Cie, 1992); data reduction: REDU4 (Stoe & Cie, 1992); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecule of the title compound in the crystal. Thermal ellipsoids represent 50% probability levels.

Bis(1H-pyrazole-κN³)bis(2,4,6-triisopropylbenzoato- κO)cobalt(II) top

Crystal data top

[Co(C₁₆H₂₃O₂)₂(C₃H₄N₂)₂]	F(000) = 1476
M_r = 689.78	D_x = 1.191 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 25 reflections
a = 9.6146 (19) Å	θ = 15–25°
b = 12.792 (3) Å	µ = 0.49 mm⁻¹
c = 31.275 (6) Å	T = 153 K
V = 3846.5 (13) Å³	Platelet, violet
Z = 4	0.80 × 0.50 × 0.10 mm

Data collection top

Stoe STADI4 diffractometer	2073 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.071
Graphite monochromator	θ_max = 25.0°, θ_min = 2.5°
ω–θ–scans	h = −11→11
Absorption correction: ψ scan (North et al., 1968)	k = −15→0
T_min = 0.696, T_max = 0.953	l = −37→0
6256 measured reflections	3 standard reflections every 120 min
3378 independent reflections	intensity decay: 3%

Refinement top

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.173	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0566P)² + 5.530P] where P = (F_o² + 2F_c²)/3
3378 reflections	(Δ/σ)_max < 0.001
213 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

[Co(C₁₆H₂₃O₂)₂(C₃H₄N₂)₂]	V = 3846.5 (13) Å³
M_r = 689.78	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 9.6146 (19) Å	µ = 0.49 mm⁻¹
b = 12.792 (3) Å	T = 153 K
c = 31.275 (6) Å	0.80 × 0.50 × 0.10 mm

Data collection top

Stoe STADI4 diffractometer	2073 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.071
T_min = 0.696, T_max = 0.953	3 standard reflections every 120 min
6256 measured reflections	intensity decay: 3%
3378 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.173	H-atom parameters constrained
S = 1.09	Δρ_max = 0.43 e Å⁻³
3378 reflections	Δρ_min = −0.48 e Å⁻³
213 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

	x	y	z	U_iso*/U_eq
Co1	0.0000	0.38310 (6)	0.2500	0.0350 (3)
O1	0.0464 (3)	0.4910 (2)	0.20630 (10)	0.0408 (8)
O2	0.0446 (4)	0.3536 (2)	0.16381 (11)	0.0516 (9)
N1	0.1650 (4)	0.2895 (3)	0.25715 (12)	0.0407 (9)
N2	0.2189 (6)	0.2259 (4)	0.22795 (17)	0.0756 (15)
H2	0.1940	0.2265	0.2009	0.091*
C1	0.1346 (5)	0.5130 (4)	0.13559 (15)	0.0406 (11)
C2	0.2789 (5)	0.5234 (4)	0.13413 (17)	0.0514 (13)
C3	0.3346 (6)	0.5847 (5)	0.1010 (2)	0.0731 (18)
H3	0.4323	0.5955	0.0999	0.088*
C4	0.2509 (7)	0.6304 (5)	0.0697 (2)	0.0778 (19)
C5	0.1112 (7)	0.6181 (5)	0.07273 (19)	0.0701 (17)
H5	0.0537	0.6506	0.0519	0.084*
C6	0.0485 (5)	0.5603 (4)	0.10495 (16)	0.0501 (13)
C7	0.3722 (6)	0.4637 (5)	0.16474 (19)	0.0630 (16)
H7A	0.3170	0.4485	0.1911	0.076*
C8	0.4125 (7)	0.3596 (5)	0.1447 (2)	0.090 (2)
H8A	0.3282	0.3214	0.1365	0.135*
H8B	0.4656	0.3182	0.1654	0.135*
H8C	0.4696	0.3722	0.1193	0.135*
C9	0.5041 (7)	0.5219 (6)	0.1784 (3)	0.099 (2)
H9A	0.4785	0.5884	0.1918	0.149*
H9B	0.5622	0.5354	0.1532	0.149*
H9C	0.5561	0.4791	0.1989	0.149*
C10	0.3147 (9)	0.6955 (6)	0.0337 (3)	0.113 (3)
H10A	0.2387	0.6935	0.0119	0.135*
C11	0.4247 (10)	0.6439 (8)	0.0113 (3)	0.143 (4)
H11A	0.4581	0.6889	−0.0119	0.214*
H11B	0.3901	0.5780	−0.0007	0.214*
H11C	0.5013	0.6293	0.0311	0.214*
C12	0.3206 (11)	0.8054 (6)	0.0431 (2)	0.134 (4)
H12A	0.3590	0.8429	0.0185	0.200*
H12B	0.3800	0.8170	0.0681	0.200*
H12C	0.2266	0.8313	0.0491	0.200*
C13	−0.1072 (6)	0.5466 (4)	0.10610 (17)	0.0563 (14)
H13A	−0.1330	0.5261	0.1359	0.068*
C14	−0.1865 (6)	0.6474 (5)	0.0955 (2)	0.079 (2)
H14A	−0.1570	0.7032	0.1150	0.118*
H14B	−0.2866	0.6353	0.0988	0.118*
H14C	−0.1666	0.6680	0.0659	0.118*
C15	−0.1521 (8)	0.4578 (6)	0.0765 (2)	0.106 (3)
H15A	−0.1009	0.3941	0.0839	0.160*
H15B	−0.1320	0.4769	0.0468	0.160*
H15C	−0.2521	0.4455	0.0798	0.160*
C16	0.2320 (6)	0.2617 (4)	0.29427 (18)	0.0594 (15)
H16	0.2176	0.2921	0.3216	0.071*
C17	0.3225 (6)	0.1830 (4)	0.2852 (2)	0.0651 (17)
H17	0.3820	0.1489	0.3050	0.078*
C18	0.3129 (4)	0.1623 (3)	0.24355 (14)	0.0316 (10)
H18	0.3642	0.1113	0.2281	0.038*
C19	0.0713 (5)	0.4460 (4)	0.16973 (15)	0.0375 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0309 (4)	0.0278 (4)	0.0463 (5)	0.000	0.0002 (4)	0.000
O1	0.0410 (18)	0.0424 (18)	0.0391 (18)	0.0000 (14)	0.0033 (15)	0.0010 (15)
O2	0.060 (2)	0.0385 (19)	0.057 (2)	−0.0102 (16)	0.0027 (17)	−0.0018 (16)
N1	0.040 (2)	0.0349 (19)	0.048 (3)	0.0090 (17)	−0.0004 (19)	−0.0039 (19)
N2	0.079 (4)	0.069 (3)	0.079 (4)	−0.004 (3)	0.001 (3)	−0.002 (3)
C1	0.044 (3)	0.039 (3)	0.038 (3)	0.000 (2)	0.008 (2)	0.002 (2)
C2	0.044 (3)	0.052 (3)	0.059 (3)	0.003 (2)	0.014 (3)	0.004 (3)
C3	0.055 (4)	0.070 (4)	0.095 (5)	−0.005 (3)	0.033 (4)	0.012 (4)
C4	0.079 (4)	0.065 (4)	0.090 (5)	0.014 (3)	0.038 (4)	0.032 (4)
C5	0.071 (4)	0.077 (4)	0.063 (4)	0.021 (3)	0.020 (3)	0.030 (3)
C6	0.058 (3)	0.048 (3)	0.045 (3)	0.003 (3)	0.006 (3)	0.010 (3)
C7	0.042 (3)	0.079 (4)	0.068 (4)	−0.001 (3)	0.002 (3)	0.006 (3)
C8	0.081 (5)	0.082 (5)	0.107 (6)	0.023 (4)	−0.008 (4)	0.011 (4)
C9	0.049 (3)	0.116 (6)	0.133 (7)	−0.003 (4)	−0.013 (4)	−0.012 (5)
C10	0.113 (6)	0.087 (6)	0.138 (7)	0.013 (5)	0.071 (6)	0.051 (5)
C11	0.138 (8)	0.177 (10)	0.113 (7)	0.020 (7)	0.069 (6)	0.060 (7)
C12	0.221 (11)	0.100 (6)	0.079 (5)	−0.080 (7)	0.038 (6)	0.004 (5)
C13	0.052 (3)	0.069 (4)	0.048 (3)	0.002 (3)	0.000 (3)	0.008 (3)
C14	0.054 (4)	0.099 (5)	0.084 (5)	0.023 (4)	0.002 (3)	0.025 (4)
C15	0.076 (5)	0.121 (7)	0.122 (7)	−0.009 (5)	−0.014 (5)	−0.031 (5)
C16	0.054 (3)	0.069 (4)	0.055 (3)	0.024 (3)	−0.008 (3)	−0.007 (3)
C17	0.046 (3)	0.062 (4)	0.088 (5)	0.026 (3)	−0.006 (3)	0.017 (3)
C18	0.034 (2)	0.0270 (19)	0.034 (3)	0.0153 (18)	0.002 (2)	0.0022 (19)
C19	0.032 (2)	0.045 (3)	0.036 (3)	0.000 (2)	−0.004 (2)	0.001 (2)

Geometric parameters (Å, º) top

Co1—O1ⁱ	1.993 (3)	C8—H8C	0.9800
Co1—O1	1.993 (3)	C9—H9A	0.9800
Co1—N1	2.000 (4)	C9—H9B	0.9800
Co1—N1ⁱ	2.000 (4)	C9—H9C	0.9800
O1—C19	1.303 (5)	C10—C11	1.431 (10)
O2—C19	1.223 (5)	C10—C12	1.437 (10)
N1—N2	1.328 (6)	C10—H10A	1.0000
N1—C16	1.375 (6)	C11—H11A	0.9800
N2—C18	1.310 (6)	C11—H11B	0.9800
N2—H2	0.8800	C11—H11C	0.9800
C1—C2	1.394 (7)	C12—H12A	0.9800
C1—C6	1.403 (7)	C12—H12B	0.9800
C1—C19	1.499 (6)	C12—H12C	0.9800
C2—C3	1.404 (7)	C13—C15	1.527 (8)
C2—C7	1.518 (7)	C13—C14	1.534 (8)
C3—C4	1.397 (9)	C13—H13A	1.0000
C3—H3	0.9500	C14—H14A	0.9800
C4—C5	1.355 (9)	C14—H14B	0.9800
C4—C10	1.529 (8)	C14—H14C	0.9800
C5—C6	1.388 (7)	C15—H15A	0.9800
C5—H5	0.9500	C15—H15B	0.9800
C6—C13	1.507 (8)	C15—H15C	0.9800
C7—C8	1.522 (8)	C16—C17	1.360 (7)
C7—C9	1.531 (8)	C16—H16	0.9500
C7—H7A	1.0000	C17—C18	1.331 (7)
C8—H8A	0.9800	C17—H17	0.9500
C8—H8B	0.9800	C18—H18	0.9500

O1ⁱ—Co1—O1	92.32 (18)	C11—C10—C12	121.6 (8)
O1ⁱ—Co1—N1	121.02 (14)	C11—C10—C4	113.9 (6)
O1—Co1—N1	108.28 (14)	C12—C10—C4	113.5 (7)
O1ⁱ—Co1—N1ⁱ	108.28 (14)	C11—C10—H10A	101.2
O1—Co1—N1ⁱ	121.02 (14)	C12—C10—H10A	101.2
N1—Co1—N1ⁱ	106.5 (2)	C4—C10—H10A	101.2
C19—O1—Co1	109.7 (3)	C10—C11—H11A	109.5
N2—N1—C16	103.8 (4)	C10—C11—H11B	109.5
N2—N1—Co1	126.8 (3)	H11A—C11—H11B	109.5
C16—N1—Co1	128.4 (3)	C10—C11—H11C	109.5
C18—N2—N1	113.2 (5)	H11A—C11—H11C	109.5
C18—N2—H2	123.4	H11B—C11—H11C	109.5
N1—N2—H2	123.4	C10—C12—H12A	109.5
C2—C1—C6	121.6 (5)	C10—C12—H12B	109.5
C2—C1—C19	118.8 (4)	H12A—C12—H12B	109.5
C6—C1—C19	119.5 (4)	C10—C12—H12C	109.5
C1—C2—C3	117.2 (5)	H12A—C12—H12C	109.5
C1—C2—C7	121.3 (5)	H12B—C12—H12C	109.5
C3—C2—C7	121.4 (5)	C6—C13—C15	110.6 (5)
C4—C3—C2	122.1 (6)	C6—C13—C14	113.0 (5)
C4—C3—H3	118.9	C15—C13—C14	110.7 (5)
C2—C3—H3	118.9	C6—C13—H13A	107.4
C5—C4—C3	118.2 (5)	C15—C13—H13A	107.4
C5—C4—C10	120.9 (7)	C14—C13—H13A	107.4
C3—C4—C10	120.9 (7)	C13—C14—H14A	109.5
C4—C5—C6	122.9 (6)	C13—C14—H14B	109.5
C4—C5—H5	118.5	H14A—C14—H14B	109.5
C6—C5—H5	118.5	C13—C14—H14C	109.5
C5—C6—C1	117.9 (5)	H14A—C14—H14C	109.5
C5—C6—C13	120.7 (5)	H14B—C14—H14C	109.5
C1—C6—C13	121.3 (5)	C13—C15—H15A	109.5
C2—C7—C8	109.3 (5)	C13—C15—H15B	109.5
C2—C7—C9	114.9 (5)	H15A—C15—H15B	109.5
C8—C7—C9	109.2 (5)	C13—C15—H15C	109.5
C2—C7—H7A	107.7	H15A—C15—H15C	109.5
C8—C7—H7A	107.7	H15B—C15—H15C	109.5
C9—C7—H7A	107.7	C17—C16—N1	108.3 (5)
C7—C8—H8A	109.5	C17—C16—H16	125.8
C7—C8—H8B	109.5	N1—C16—H16	125.8
H8A—C8—H8B	109.5	C18—C17—C16	107.9 (5)
C7—C8—H8C	109.5	C18—C17—H17	126.0
H8A—C8—H8C	109.5	C16—C17—H17	126.0
H8B—C8—H8C	109.5	N2—C18—C17	106.8 (4)
C7—C9—H9A	109.5	N2—C18—H18	126.6
C7—C9—H9B	109.5	C17—C18—H18	126.6
H9A—C9—H9B	109.5	O2—C19—O1	121.5 (4)
C7—C9—H9C	109.5	O2—C19—C1	122.0 (4)
H9A—C9—H9C	109.5	O1—C19—C1	116.5 (4)
H9B—C9—H9C	109.5

O1ⁱ—Co1—O1—C19	−174.0 (3)	C2—C1—C6—C13	178.5 (5)
N1—Co1—O1—C19	62.1 (3)	C19—C1—C6—C13	1.2 (8)
N1ⁱ—Co1—O1—C19	−61.0 (3)	C1—C2—C7—C8	90.8 (7)
O1ⁱ—Co1—N1—N2	−169.3 (4)	C3—C2—C7—C8	−84.0 (7)
O1—Co1—N1—N2	−64.9 (4)	C1—C2—C7—C9	−146.0 (6)
N1ⁱ—Co1—N1—N2	66.7 (4)	C3—C2—C7—C9	39.2 (8)
O1ⁱ—Co1—N1—C16	23.7 (5)	C5—C4—C10—C11	−130.1 (9)
O1—Co1—N1—C16	128.1 (4)	C3—C4—C10—C11	51.9 (11)
N1ⁱ—Co1—N1—C16	−100.4 (5)	C5—C4—C10—C12	85.1 (11)
C16—N1—N2—C18	−0.3 (6)	C3—C4—C10—C12	−92.8 (10)
Co1—N1—N2—C18	−169.9 (3)	C5—C6—C13—C15	82.9 (7)
C6—C1—C2—C3	1.0 (8)	C1—C6—C13—C15	−95.5 (6)
C19—C1—C2—C3	178.4 (5)	C5—C6—C13—C14	−41.9 (8)
C6—C1—C2—C7	−174.0 (5)	C1—C6—C13—C14	139.7 (5)
C19—C1—C2—C7	3.4 (8)	N2—N1—C16—C17	0.1 (6)
C1—C2—C3—C4	−2.5 (9)	Co1—N1—C16—C17	169.4 (4)
C7—C2—C3—C4	172.5 (6)	N1—C16—C17—C18	0.2 (7)
C2—C3—C4—C5	2.8 (10)	N1—N2—C18—C17	0.4 (6)
C2—C3—C4—C10	−179.2 (6)	C16—C17—C18—N2	−0.4 (6)
C3—C4—C5—C6	−1.6 (11)	Co1—O1—C19—O2	11.3 (5)
C10—C4—C5—C6	−179.6 (6)	Co1—O1—C19—C1	−168.4 (3)
C4—C5—C6—C1	0.2 (9)	C2—C1—C19—O2	−93.1 (6)
C4—C5—C6—C13	−178.2 (6)	C6—C1—C19—O2	84.3 (6)
C2—C1—C6—C5	0.1 (8)	C2—C1—C19—O1	86.6 (6)
C19—C1—C6—C5	−177.3 (5)	C6—C1—C19—O1	−95.9 (5)

Symmetry code: (i) −x, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Co(C₁₆H₂₃O₂)₂(C₃H₄N₂)₂]
M_r	689.78
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	153
a, b, c (Å)	9.6146 (19), 12.792 (3), 31.275 (6)
V (Å³)	3846.5 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.49
Crystal size (mm)	0.80 × 0.50 × 0.10

Data collection
Diffractometer	Stoe STADI4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.696, 0.953
No. of measured, independent and observed [I > 2σ(I)] reflections	6256, 3378, 2073
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.173, 1.09
No. of reflections	3378
No. of parameters	213
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.48

Computer programs: DIF4 (Stoe & Cie, 1992), REDU4 (Stoe & Cie, 1992), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 2008).

Acknowledgements

The authors thank the Otto-von-Guericke-Universität for financial support of this work.

References

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