Bis[μ-2,2′-dimethyl-1,1′-(3-oxapentane-1,5-di­yl)di-1H-benzimidazole-κ2N3:N3′]bis­[bis­(4-meth­oxy­benzoato)-κO;κ2O,O′-cobalt(II)]

Zhao, L.-P.

doi:10.1107/S160053681004568X

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page m1549

https://doi.org/10.1107/S160053681004568X

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Bis[μ-2,2′-dimethyl-1,1′-(3-oxapentane-1,5-diyl)di-1H-benzimidazole-κ²N³:N^3′]bis[bis(4-methoxybenzoato)-κO;κ²O,O′-cobalt(II)]

Lian-Peng Zhao ^a ^*

^aBoHai University, JinZhou, LiaoNing, 121013, People's Republic of China
^*Correspondence e-mail: lianpengzhao@yahoo.com.cn

(Received 31 October 2010; accepted 7 November 2010; online 13 November 2010)

The complete molecule of the title complex, [Co₂(C₈H₇O₃)₄(C₂₀H₂₂N₄O)₂], is a dimer of the paddle-wheel-type generated by crystallographic inversion symmetry. The Co^II ion is pentacoordinated by three O atoms from two 4-methoxybenzoate anions (one bidentate and one monodentate) and two N atoms from two 2,2′-bis(2-methyl-1H-benzimidazole)ether ligands. This results in a very distorted trigonal–bipyramidal geometry for the metal ion, with both N atoms in equatorial sites. The dihedral angle between the benzimidazole ring systems in the ligand is 60.04 (8)°. The configuration of the molecule is supported by intramolecular C—H⋯O hydrogen bonds.

Related literature

For background to benzimidazole ligands in coordination polymers, see: Hoskins et al. (1997 ). For a related structure, see: Dimitrou et al. (1999 ).

Experimental

Crystal data

[Co₂(C₈H₇O₃)₄(C₂₀H₂₂N₄O)₂]
M_r = 1391.24
Monoclinic, P 2₁ /n
a = 12.4127 (3) Å
b = 16.3933 (4) Å
c = 17.6106 (5) Å
β = 109.577 (3)°
V = 3376.34 (15) Å³
Z = 2
Mo Kα radiation
μ = 0.56 mm⁻¹
T = 293 K
0.32 × 0.28 × 0.24 mm

Data collection

Oxford Diffraction Gemini R Ultra CCD diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon England.]$ ) T_min = 0.829, T_max = 0.889
14632 measured reflections
7801 independent reflections
3677 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.081
S = 0.75
7801 reflections
433 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—O6	1.9694 (14)
Co1—O3	2.0362 (18)
Co1—N1	2.0524 (18)
Co1—N4ⁱ	2.0598 (18)
Co1—O2	2.374 (2)
Symmetry code: (i) -x+1, -y, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H015⋯O6ⁱ	0.93	2.46	3.111 (3)	127
C8—H8C⋯O2	0.96	2.50	3.255 (3)	136
C20—H03B⋯O2ⁱ	0.96	2.42	3.150 (3)	132
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681004568X/hb5721sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681004568X/hb5721Isup2.hkl

checkCIF report

Comment top

Bis(imidazole) ligands with –CH₂– spacers are a good candidate for N-donor bridging ligand (Hoskins et al., 1997). Up to now, 2,2'-bis(2-methyl-1H-benzimidazole)ether ligands, as a flexible ligand, is rarely investigated in constructing coordination polymers.

In the title compound (Fig. 1), the Co^II ion is pentacoordinated by three O atoms from two 4-methoxybenzoate anions, and two N atoms from two 2,2'-bis(2-methyl-1H-benzimidazole)ether ligand. The Co—O distances are found in the range from 1.9694 (14) to 2.374 (2) Å, which is similar to previous report (Dimitrou et al., 1999). The Co—N distances are 2.0524 (18) and 2.0598 (18) Å, respectively. The crystal structure is stabilized by a weak intermolecular C—H···O hydrogen bond between the benzene H atom of 2-methyl-1H-benzimidazole ring and the O atom of diethyl ether group, with a C17—H015···O6; the methyl H atoms of 2-methyl-1H-benzimidazole ligands and the carboxylate O atoms with C8—H8c—O2 and C20—H03B—O2 (Table 1 & Fig. 2).

Related literature top

For background to benzimidazole ligands in coordination polymers, see: Hoskins et al. (1997). For a related structure, see: Dimitrou et al. (1999).

Experimental top

An aqueous solution (10 ml) of 4-methoxybenzoic acid (0.072 g, 0.4 mmol), 2,2'-bis(2-methylbenzimidazole)ether (0.065 g, 0.2 mmol) and Co(Ac)₂ (0.049 g, 0.2 mmol) was added in and sealed in 18 ml Teflon-lined stainless steel container. The container was heated to 130 °C and held at that temperature for 72 h, then cooled to room temperature at a rate of 10 °C.h^-1. And then the title compound was isolated as purple blocks.

Structure description top

For background to benzimidazole ligands in coordination polymers, see: Hoskins et al. (1997). For a related structure, see: Dimitrou et al. (1999).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis CCD (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. [symmetry code: (i) - x + 1, - y, - z + 1.]
	Fig. 2. C—H···O interactions (dotted lines) in the title compound.: [symmetry code: (i) -x + 1, -y, -z + 1.]

Bis[µ-2,2'-dimethyl-1,1'-(3-oxapentane-1,5-diyl)di-1H-benzimidazole- κ²N³:N^3']bis[bis(4-methoxybenzoato)-κO; κ²O,O'-cobalt(II)] top

Crystal data top

[Co₂(C₈H₇O₃)₄(C₂₀H₂₂N₄O)₂]	F(000) = 1452
M_r = 1391.24	D_x = 1.368 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7801 reflections
a = 12.4127 (3) Å	θ = 3.0–29.2°
b = 16.3933 (4) Å	µ = 0.56 mm⁻¹
c = 17.6106 (5) Å	T = 293 K
β = 109.577 (3)°	Block, purple
V = 3376.34 (15) Å³	0.32 × 0.28 × 0.24 mm
Z = 2

Data collection top

Oxford Diffraction Gemini R Ultra CCD diffractometer	7801 independent reflections
Radiation source: fine-focus sealed tube	3677 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 10.0 pixels mm^-1	θ_max = 29.2°, θ_min = 3.1°
ω scans	h = −15→17
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −21→22
T_min = 0.829, T_max = 0.889	l = −23→23
14632 measured reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.081	H-atom parameters constrained
S = 0.75	w = 1/[σ²(F_o²) + (0.0363P)²] where P = (F_o² + 2F_c²)/3
7801 reflections	(Δ/σ)_max = 0.002
433 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

[Co₂(C₈H₇O₃)₄(C₂₀H₂₂N₄O)₂]	V = 3376.34 (15) Å³
M_r = 1391.24	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.4127 (3) Å	µ = 0.56 mm⁻¹
b = 16.3933 (4) Å	T = 293 K
c = 17.6106 (5) Å	0.32 × 0.28 × 0.24 mm
β = 109.577 (3)°

Data collection top

Oxford Diffraction Gemini R Ultra CCD diffractometer	7801 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	3677 reflections with I > 2σ(I)
T_min = 0.829, T_max = 0.889	R_int = 0.030
14632 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.081	H-atom parameters constrained
S = 0.75	Δρ_max = 0.48 e Å⁻³
7801 reflections	Δρ_min = −0.24 e Å⁻³
433 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.78779 (2)	0.131671 (18)	0.654674 (17)	0.03902 (10)
C1	0.85504 (17)	−0.01846 (14)	0.47885 (14)	0.0403 (6)
C2	0.89543 (19)	−0.09166 (17)	0.45938 (17)	0.0565 (7)
H030	0.8957	−0.1022	0.4076	0.068*
C3	0.9350 (2)	−0.14773 (16)	0.5202 (2)	0.0657 (8)
H026	0.9626	−0.1976	0.5094	0.079*
C4	0.9347 (2)	−0.13176 (17)	0.59687 (19)	0.0636 (8)
H046	0.9621	−0.1713	0.6365	0.076*
C5	0.89485 (18)	−0.05868 (15)	0.61701 (15)	0.0495 (6)
H019	0.8951	−0.0483	0.6690	0.059*
C6	0.85452 (17)	−0.00168 (13)	0.55553 (13)	0.0364 (5)
C7	0.78846 (17)	0.10552 (13)	0.48290 (13)	0.0386 (6)
C8	0.7453 (2)	0.18927 (14)	0.45810 (14)	0.0581 (7)
H8A	0.7340	0.1966	0.4019	0.087*
H8B	0.8000	0.2284	0.4891	0.087*
H8C	0.6740	0.1969	0.4673	0.087*
C9	0.79201 (19)	0.05843 (17)	0.34709 (13)	0.0538 (7)
H9A	0.8564	0.0359	0.3346	0.065*
H9B	0.7852	0.1156	0.3322	0.065*
C10	0.68383 (19)	0.01401 (16)	0.29879 (14)	0.0551 (7)
H10A	0.6757	0.0162	0.2421	0.066*
H10B	0.6902	−0.0429	0.3149	0.066*
C11	0.53616 (19)	0.11094 (16)	0.25483 (16)	0.0604 (8)
H11A	0.5161	0.0914	0.1998	0.073*
H11B	0.5895	0.1558	0.2621	0.073*
C12	0.4298 (2)	0.13882 (15)	0.27170 (16)	0.0590 (7)
H12A	0.4511	0.1590	0.3266	0.071*
H12B	0.3942	0.1832	0.2356	0.071*
C13	0.27905 (18)	0.04282 (15)	0.18685 (14)	0.0425 (6)
C14	0.2593 (2)	0.07031 (17)	0.10893 (16)	0.0606 (7)
H047	0.2954	0.1164	0.0982	0.073*
C15	0.1834 (2)	0.0255 (2)	0.04845 (16)	0.0692 (8)
H031	0.1678	0.0419	−0.0047	0.083*
C16	0.1298 (2)	−0.04286 (19)	0.06417 (15)	0.0614 (8)
H037	0.0792	−0.0713	0.0213	0.074*
C17	0.14893 (18)	−0.07034 (15)	0.14168 (13)	0.0476 (6)
H015	0.1121	−0.1163	0.1520	0.057*
C18	0.22604 (17)	−0.02586 (14)	0.20371 (12)	0.0376 (5)
C19	0.33864 (17)	0.02086 (14)	0.31804 (14)	0.0419 (6)
C20	0.4034 (2)	0.03192 (16)	0.40569 (13)	0.0584 (7)
H03A	0.4512	0.0793	0.4131	0.088*
H03B	0.4500	−0.0153	0.4258	0.088*
H03C	0.3505	0.0388	0.4344	0.088*
C21	0.50942 (19)	0.27294 (15)	0.61817 (15)	0.0480 (6)
C22	0.52284 (19)	0.34163 (15)	0.66575 (15)	0.0516 (7)
H024	0.5952	0.3554	0.7006	0.062*
C23	0.43083 (19)	0.39010 (15)	0.66240 (14)	0.0504 (6)
H029	0.4414	0.4364	0.6946	0.061*
C24	0.32260 (17)	0.36994 (15)	0.61112 (13)	0.0423 (6)
C25	0.3085 (2)	0.30181 (15)	0.56284 (14)	0.0490 (6)
H034	0.2364	0.2880	0.5276	0.059*
C26	0.4016 (2)	0.25449 (15)	0.56708 (14)	0.0541 (7)
H023	0.3913	0.2086	0.5344	0.065*
C27	0.6097 (3)	0.21856 (18)	0.6219 (2)	0.0646 (8)
C28	0.1242 (2)	0.40712 (18)	0.55740 (16)	0.0730 (9)
H04A	0.0725	0.4468	0.5658	0.109*
H04B	0.0988	0.3534	0.5650	0.109*
H04C	0.1260	0.4121	0.5035	0.109*
C29	1.13722 (17)	0.17700 (13)	0.74857 (13)	0.0355 (5)
C30	1.21576 (17)	0.21342 (13)	0.71996 (13)	0.0408 (6)
H033	1.1897	0.2450	0.6735	0.049*
C31	1.33219 (17)	0.20458 (14)	0.75815 (14)	0.0448 (6)
H022	1.3837	0.2289	0.7370	0.054*
C32	1.37090 (19)	0.15926 (14)	0.82796 (14)	0.0447 (6)
C33	1.29372 (19)	0.12518 (15)	0.85978 (14)	0.0488 (6)
H032	1.3200	0.0970	0.9083	0.059*
C34	1.17833 (18)	0.13266 (14)	0.82017 (13)	0.0439 (6)
H014	1.1271	0.1080	0.8412	0.053*
C35	1.01124 (18)	0.18316 (15)	0.70171 (14)	0.0412 (6)
C36	1.5609 (2)	0.14637 (19)	0.82543 (18)	0.0758 (9)
H04D	1.6368	0.1350	0.8612	0.114*
H04E	1.5593	0.1994	0.8019	0.114*
H04F	1.5389	0.1060	0.7835	0.114*
N1	0.81165 (14)	0.07684 (10)	0.55674 (10)	0.0370 (4)
N2	0.81263 (14)	0.05087 (12)	0.43346 (10)	0.0406 (5)
N3	0.34858 (14)	0.07201 (11)	0.26072 (11)	0.0447 (5)
N4	0.26514 (13)	−0.03898 (11)	0.28711 (10)	0.0380 (4)
O1	0.58565 (13)	0.04771 (9)	0.30952 (9)	0.0513 (4)
O2	0.59500 (18)	0.15921 (14)	0.57565 (13)	0.0890 (7)
O3	0.70491 (15)	0.23292 (11)	0.67326 (14)	0.0804 (6)
O4	0.23632 (13)	0.42058 (10)	0.61380 (10)	0.0609 (5)
O5	0.97677 (12)	0.22669 (10)	0.64168 (10)	0.0526 (4)
O6	0.94624 (12)	0.14002 (11)	0.72914 (9)	0.0554 (5)
O7	1.48382 (13)	0.14450 (12)	0.86905 (10)	0.0731 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.03659 (16)	0.04231 (18)	0.04015 (18)	−0.00346 (15)	0.01550 (13)	−0.00498 (16)
C1	0.0299 (11)	0.0410 (15)	0.0488 (15)	−0.0039 (11)	0.0118 (11)	−0.0119 (12)
C2	0.0386 (13)	0.0638 (18)	0.0658 (18)	−0.0066 (13)	0.0158 (13)	−0.0274 (16)
C3	0.0438 (14)	0.0472 (18)	0.100 (2)	0.0032 (13)	0.0161 (16)	−0.0228 (18)
C4	0.0500 (15)	0.0445 (16)	0.091 (2)	0.0081 (14)	0.0161 (15)	0.0103 (16)
C5	0.0454 (13)	0.0489 (16)	0.0532 (15)	0.0048 (12)	0.0154 (12)	0.0050 (13)
C6	0.0323 (11)	0.0365 (14)	0.0418 (14)	−0.0036 (10)	0.0143 (10)	−0.0048 (11)
C7	0.0377 (12)	0.0388 (14)	0.0414 (14)	−0.0060 (10)	0.0159 (11)	0.0002 (11)
C8	0.0724 (17)	0.0465 (16)	0.0559 (16)	0.0027 (14)	0.0223 (13)	0.0081 (13)
C9	0.0452 (13)	0.0805 (19)	0.0418 (15)	−0.0028 (13)	0.0226 (12)	−0.0048 (13)
C10	0.0534 (15)	0.0639 (18)	0.0432 (15)	0.0025 (14)	0.0099 (12)	−0.0089 (13)
C11	0.0445 (14)	0.0584 (18)	0.0762 (18)	−0.0063 (13)	0.0174 (13)	0.0259 (15)
C12	0.0530 (15)	0.0412 (15)	0.0800 (19)	−0.0060 (13)	0.0188 (13)	0.0124 (14)
C13	0.0346 (12)	0.0507 (15)	0.0443 (15)	0.0092 (11)	0.0158 (11)	0.0094 (12)
C14	0.0545 (15)	0.0720 (19)	0.0570 (17)	0.0119 (15)	0.0208 (14)	0.0236 (15)
C15	0.0663 (18)	0.102 (2)	0.0412 (16)	0.0232 (18)	0.0205 (15)	0.0208 (16)
C16	0.0471 (15)	0.094 (2)	0.0393 (16)	0.0109 (16)	0.0097 (13)	−0.0081 (15)
C17	0.0373 (12)	0.0633 (17)	0.0426 (14)	0.0018 (12)	0.0139 (11)	−0.0062 (13)
C18	0.0319 (11)	0.0471 (14)	0.0352 (13)	0.0068 (11)	0.0131 (10)	0.0011 (11)
C19	0.0325 (12)	0.0476 (15)	0.0476 (14)	−0.0042 (11)	0.0161 (11)	−0.0021 (12)
C20	0.0495 (14)	0.0718 (19)	0.0480 (15)	−0.0159 (13)	0.0086 (12)	−0.0107 (13)
C21	0.0462 (14)	0.0453 (16)	0.0622 (17)	0.0049 (12)	0.0312 (13)	0.0082 (13)
C22	0.0394 (13)	0.0496 (16)	0.0640 (17)	−0.0047 (12)	0.0147 (12)	0.0030 (13)
C23	0.0496 (14)	0.0457 (15)	0.0547 (15)	−0.0037 (12)	0.0158 (12)	−0.0076 (12)
C24	0.0420 (13)	0.0437 (14)	0.0440 (13)	0.0039 (12)	0.0180 (11)	0.0003 (12)
C25	0.0478 (14)	0.0511 (16)	0.0468 (15)	−0.0040 (13)	0.0142 (12)	−0.0057 (13)
C26	0.0627 (17)	0.0464 (15)	0.0573 (16)	0.0002 (14)	0.0256 (14)	−0.0089 (13)
C27	0.068 (2)	0.0535 (19)	0.086 (2)	0.0103 (16)	0.0438 (18)	0.0239 (17)
C28	0.0494 (15)	0.085 (2)	0.0741 (19)	0.0162 (15)	0.0070 (14)	0.0024 (16)
C29	0.0339 (11)	0.0330 (12)	0.0432 (14)	−0.0032 (10)	0.0176 (10)	−0.0074 (11)
C30	0.0419 (13)	0.0370 (13)	0.0434 (13)	0.0013 (11)	0.0142 (11)	0.0033 (11)
C31	0.0358 (12)	0.0461 (15)	0.0564 (16)	−0.0041 (11)	0.0205 (11)	0.0006 (12)
C32	0.0379 (13)	0.0468 (15)	0.0476 (15)	0.0057 (11)	0.0120 (12)	−0.0079 (12)
C33	0.0539 (15)	0.0495 (15)	0.0432 (14)	0.0120 (13)	0.0165 (12)	0.0063 (12)
C34	0.0474 (13)	0.0411 (13)	0.0497 (14)	−0.0044 (12)	0.0246 (11)	−0.0009 (13)
C35	0.0394 (13)	0.0437 (15)	0.0446 (15)	−0.0020 (12)	0.0193 (12)	−0.0161 (13)
C36	0.0433 (14)	0.090 (2)	0.094 (2)	0.0140 (15)	0.0239 (15)	−0.0113 (18)
N1	0.0407 (10)	0.0347 (11)	0.0382 (11)	0.0001 (9)	0.0167 (8)	−0.0010 (9)
N2	0.0409 (10)	0.0501 (12)	0.0348 (11)	−0.0058 (9)	0.0178 (9)	−0.0049 (10)
N3	0.0380 (10)	0.0427 (12)	0.0528 (13)	−0.0033 (9)	0.0145 (10)	0.0080 (10)
N4	0.0326 (9)	0.0463 (12)	0.0356 (11)	−0.0060 (9)	0.0122 (8)	−0.0019 (9)
O1	0.0439 (9)	0.0492 (10)	0.0611 (11)	0.0013 (8)	0.0180 (8)	0.0112 (9)
O2	0.1034 (16)	0.0903 (17)	0.0858 (15)	0.0400 (13)	0.0482 (12)	−0.0019 (13)
O3	0.0442 (11)	0.0576 (12)	0.1416 (18)	0.0037 (9)	0.0341 (11)	0.0070 (12)
O4	0.0474 (9)	0.0658 (12)	0.0642 (11)	0.0129 (9)	0.0115 (9)	−0.0133 (9)
O5	0.0443 (9)	0.0537 (11)	0.0530 (11)	0.0047 (8)	0.0074 (8)	−0.0008 (9)
O6	0.0406 (9)	0.0787 (12)	0.0501 (10)	−0.0164 (9)	0.0196 (8)	−0.0075 (9)
O7	0.0366 (9)	0.1133 (17)	0.0645 (12)	0.0192 (10)	0.0106 (9)	0.0039 (11)

Geometric parameters (Å, º) top

Co1—O6	1.9694 (14)	C17—C18	1.393 (3)
Co1—O3	2.0362 (18)	C17—H015	0.9300
Co1—N1	2.0524 (18)	C18—N4	1.401 (3)
Co1—N4ⁱ	2.0598 (18)	C19—N4	1.326 (3)
Co1—O2	2.374 (2)	C19—N3	1.349 (3)
C1—C6	1.380 (3)	C19—C20	1.493 (3)
C1—C2	1.387 (3)	C20—H03A	0.9600
C1—N2	1.388 (3)	C20—H03B	0.9600
C2—C3	1.372 (4)	C20—H03C	0.9600
C2—H030	0.9300	C21—C26	1.373 (3)
C3—C4	1.377 (4)	C21—C22	1.380 (3)
C3—H026	0.9300	C21—C27	1.515 (4)
C4—C5	1.387 (3)	C22—C23	1.376 (3)
C4—H046	0.9300	C22—H024	0.9300
C5—C6	1.390 (3)	C23—C24	1.384 (3)
C5—H019	0.9300	C23—H029	0.9300
C6—N1	1.396 (3)	C24—O4	1.368 (3)
C7—N1	1.321 (3)	C24—C25	1.379 (3)
C7—N2	1.351 (3)	C25—C26	1.372 (3)
C7—C8	1.485 (3)	C25—H034	0.9300
C8—H8A	0.9600	C26—H023	0.9300
C8—H8B	0.9600	C27—O2	1.243 (3)
C8—H8C	0.9600	C27—O3	1.246 (3)
C9—N2	1.461 (3)	C28—O4	1.430 (3)
C9—C10	1.514 (3)	C28—H04A	0.9600
C9—H9A	0.9700	C28—H04B	0.9600
C9—H9B	0.9700	C28—H04C	0.9600
C10—O1	1.407 (3)	C29—C30	1.375 (3)
C10—H10A	0.9700	C29—C34	1.395 (3)
C10—H10B	0.9700	C29—C35	1.507 (3)
C11—O1	1.408 (3)	C30—C31	1.382 (3)
C11—C12	1.517 (3)	C30—H033	0.9300
C11—H11A	0.9700	C31—C32	1.378 (3)
C11—H11B	0.9700	C31—H022	0.9300
C12—N3	1.457 (3)	C32—O7	1.366 (2)
C12—H12A	0.9700	C32—C33	1.380 (3)
C12—H12B	0.9700	C33—C34	1.372 (3)
C13—N3	1.383 (3)	C33—H032	0.9300
C13—C18	1.386 (3)	C34—H014	0.9300
C13—C14	1.386 (3)	C35—O5	1.228 (3)
C14—C15	1.374 (4)	C35—O6	1.283 (3)
C14—H047	0.9300	C36—O7	1.414 (3)
C15—C16	1.379 (4)	C36—H04D	0.9600
C15—H031	0.9300	C36—H04E	0.9600
C16—C17	1.380 (3)	C36—H04F	0.9600
C16—H037	0.9300	N4—Co1ⁱ	2.0598 (18)

O6—Co1—O3	106.38 (8)	N4—C19—C20	124.9 (2)
O6—Co1—N1	101.35 (7)	N3—C19—C20	123.1 (2)
O3—Co1—N1	135.65 (8)	C19—C20—H03A	109.5
O6—Co1—N4ⁱ	97.69 (7)	C19—C20—H03B	109.5
O3—Co1—N4ⁱ	104.99 (8)	H03A—C20—H03B	109.5
N1—Co1—N4ⁱ	104.77 (7)	C19—C20—H03C	109.5
O6—Co1—O2	164.33 (8)	H03A—C20—H03C	109.5
O3—Co1—O2	58.32 (7)	H03B—C20—H03C	109.5
N1—Co1—O2	89.52 (7)	C26—C21—C22	118.1 (2)
N4ⁱ—Co1—O2	90.29 (7)	C26—C21—C27	120.4 (2)
C6—C1—C2	122.3 (2)	C22—C21—C27	121.6 (2)
C6—C1—N2	105.97 (19)	C23—C22—C21	121.0 (2)
C2—C1—N2	131.7 (2)	C23—C22—H024	119.5
C3—C2—C1	116.8 (3)	C21—C22—H024	119.5
C3—C2—H030	121.6	C22—C23—C24	120.0 (2)
C1—C2—H030	121.6	C22—C23—H029	120.0
C2—C3—C4	121.4 (3)	C24—C23—H029	120.0
C2—C3—H026	119.3	O4—C24—C25	125.03 (19)
C4—C3—H026	119.3	O4—C24—C23	115.6 (2)
C3—C4—C5	122.3 (3)	C25—C24—C23	119.4 (2)
C3—C4—H046	118.9	C26—C25—C24	119.6 (2)
C5—C4—H046	118.9	C26—C25—H034	120.2
C4—C5—C6	116.6 (2)	C24—C25—H034	120.2
C4—C5—H019	121.7	C25—C26—C21	121.9 (2)
C6—C5—H019	121.7	C25—C26—H023	119.0
C1—C6—C5	120.6 (2)	C21—C26—H023	119.0
C1—C6—N1	109.00 (19)	O2—C27—O3	121.3 (3)
C5—C6—N1	130.4 (2)	O2—C27—C21	119.6 (3)
N1—C7—N2	112.09 (19)	O3—C27—C21	119.1 (3)
N1—C7—C8	123.8 (2)	O4—C28—H04A	109.5
N2—C7—C8	124.0 (2)	O4—C28—H04B	109.5
C7—C8—H8A	109.5	H04A—C28—H04B	109.5
C7—C8—H8B	109.5	O4—C28—H04C	109.5
H8A—C8—H8B	109.5	H04A—C28—H04C	109.5
C7—C8—H8C	109.5	H04B—C28—H04C	109.5
H8A—C8—H8C	109.5	C30—C29—C34	117.89 (19)
H8B—C8—H8C	109.5	C30—C29—C35	120.2 (2)
N2—C9—C10	110.9 (2)	C34—C29—C35	121.9 (2)
N2—C9—H9A	109.5	C29—C30—C31	122.0 (2)
C10—C9—H9A	109.5	C29—C30—H033	119.0
N2—C9—H9B	109.5	C31—C30—H033	119.0
C10—C9—H9B	109.5	C32—C31—C30	119.1 (2)
H9A—C9—H9B	108.0	C32—C31—H022	120.5
O1—C10—C9	112.4 (2)	C30—C31—H022	120.5
O1—C10—H10A	109.1	O7—C32—C31	123.9 (2)
C9—C10—H10A	109.1	O7—C32—C33	116.2 (2)
O1—C10—H10B	109.1	C31—C32—C33	119.9 (2)
C9—C10—H10B	109.1	C34—C33—C32	120.4 (2)
H10A—C10—H10B	107.9	C34—C33—H032	119.8
O1—C11—C12	107.3 (2)	C32—C33—H032	119.8
O1—C11—H11A	110.3	C33—C34—C29	120.6 (2)
C12—C11—H11A	110.3	C33—C34—H014	119.7
O1—C11—H11B	110.3	C29—C34—H014	119.7
C12—C11—H11B	110.3	O5—C35—O6	124.3 (2)
H11A—C11—H11B	108.5	O5—C35—C29	120.6 (2)
N3—C12—C11	110.9 (2)	O6—C35—C29	115.1 (2)
N3—C12—H12A	109.5	O7—C36—H04D	109.5
C11—C12—H12A	109.5	O7—C36—H04E	109.5
N3—C12—H12B	109.5	H04D—C36—H04E	109.5
C11—C12—H12B	109.5	O7—C36—H04F	109.5
H12A—C12—H12B	108.1	H04D—C36—H04F	109.5
N3—C13—C18	105.72 (19)	H04E—C36—H04F	109.5
N3—C13—C14	131.8 (2)	C7—N1—C6	105.77 (18)
C18—C13—C14	122.5 (2)	C7—N1—Co1	128.77 (15)
C15—C14—C13	116.2 (3)	C6—N1—Co1	125.44 (14)
C15—C14—H047	121.9	C7—N2—C1	107.17 (18)
C13—C14—H047	121.9	C7—N2—C9	128.0 (2)
C14—C15—C16	122.0 (2)	C1—N2—C9	124.7 (2)
C14—C15—H031	119.0	C19—N3—C13	107.69 (18)
C16—C15—H031	119.0	C19—N3—C12	126.91 (18)
C15—C16—C17	122.0 (2)	C13—N3—C12	124.8 (2)
C15—C16—H037	119.0	C19—N4—C18	105.43 (18)
C17—C16—H037	119.0	C19—N4—Co1ⁱ	129.17 (15)
C16—C17—C18	116.7 (2)	C18—N4—Co1ⁱ	125.38 (14)
C16—C17—H015	121.6	C10—O1—C11	113.34 (19)
C18—C17—H015	121.6	C27—O2—Co1	82.33 (17)
C13—C18—C17	120.5 (2)	C27—O3—Co1	97.85 (18)
C13—C18—N4	109.08 (18)	C24—O4—C28	118.24 (18)
C17—C18—N4	130.4 (2)	C35—O6—Co1	113.66 (14)
N4—C19—N3	112.04 (19)	C32—O7—C36	118.0 (2)

C6—C1—C2—C3	0.3 (3)	O6—Co1—N1—C7	−117.02 (18)
N2—C1—C2—C3	178.1 (2)	O3—Co1—N1—C7	11.1 (2)
C1—C2—C3—C4	−0.1 (4)	N4ⁱ—Co1—N1—C7	141.80 (17)
C2—C3—C4—C5	−0.1 (4)	O2—Co1—N1—C7	51.62 (18)
C3—C4—C5—C6	0.2 (4)	O6—Co1—N1—C6	64.75 (17)
C2—C1—C6—C5	−0.2 (3)	O3—Co1—N1—C6	−167.17 (14)
N2—C1—C6—C5	−178.51 (18)	N4ⁱ—Co1—N1—C6	−36.44 (17)
C2—C1—C6—N1	178.64 (18)	O2—Co1—N1—C6	−126.61 (16)
N2—C1—C6—N1	0.3 (2)	N1—C7—N2—C1	−0.2 (2)
C4—C5—C6—C1	0.0 (3)	C8—C7—N2—C1	177.53 (19)
C4—C5—C6—N1	−178.6 (2)	N1—C7—N2—C9	175.86 (18)
N2—C9—C10—O1	63.5 (3)	C8—C7—N2—C9	−6.4 (3)
O1—C11—C12—N3	−60.1 (3)	C6—C1—N2—C7	−0.1 (2)
N3—C13—C14—C15	179.9 (2)	C2—C1—N2—C7	−178.2 (2)
C18—C13—C14—C15	0.1 (4)	C6—C1—N2—C9	−176.30 (18)
C13—C14—C15—C16	0.0 (4)	C2—C1—N2—C9	5.6 (3)
C14—C15—C16—C17	0.2 (4)	C10—C9—N2—C7	−98.9 (3)
C15—C16—C17—C18	−0.4 (4)	C10—C9—N2—C1	76.4 (3)
N3—C13—C18—C17	179.77 (19)	N4—C19—N3—C13	−1.5 (3)
C14—C13—C18—C17	−0.4 (3)	C20—C19—N3—C13	178.7 (2)
N3—C13—C18—N4	−1.2 (2)	N4—C19—N3—C12	−172.9 (2)
C14—C13—C18—N4	178.6 (2)	C20—C19—N3—C12	7.3 (4)
C16—C17—C18—C13	0.6 (3)	C18—C13—N3—C19	1.6 (2)
C16—C17—C18—N4	−178.3 (2)	C14—C13—N3—C19	−178.2 (3)
C26—C21—C22—C23	0.3 (4)	C18—C13—N3—C12	173.2 (2)
C27—C21—C22—C23	−179.3 (2)	C14—C13—N3—C12	−6.6 (4)
C21—C22—C23—C24	0.4 (4)	C11—C12—N3—C19	93.8 (3)
C22—C23—C24—O4	178.2 (2)	C11—C12—N3—C13	−76.3 (3)
C22—C23—C24—C25	−1.0 (4)	N3—C19—N4—C18	0.8 (2)
O4—C24—C25—C26	−178.3 (2)	C20—C19—N4—C18	−179.5 (2)
C23—C24—C25—C26	0.9 (4)	N3—C19—N4—Co1ⁱ	−177.77 (14)
C24—C25—C26—C21	−0.2 (4)	C20—C19—N4—Co1ⁱ	2.0 (3)
C22—C21—C26—C25	−0.4 (4)	C13—C18—N4—C19	0.3 (2)
C27—C21—C26—C25	179.2 (2)	C17—C18—N4—C19	179.2 (2)
C26—C21—C27—O2	3.5 (4)	C13—C18—N4—Co1ⁱ	178.91 (14)
C22—C21—C27—O2	−176.9 (3)	C17—C18—N4—Co1ⁱ	−2.2 (3)
C26—C21—C27—O3	−174.3 (2)	C9—C10—O1—C11	88.7 (2)
C22—C21—C27—O3	5.3 (4)	C12—C11—O1—C10	178.01 (19)
C34—C29—C30—C31	2.5 (3)	O3—C27—O2—Co1	4.4 (3)
C35—C29—C30—C31	−175.5 (2)	C21—C27—O2—Co1	−173.3 (2)
C29—C30—C31—C32	−1.4 (3)	O6—Co1—O2—C27	−16.1 (4)
C30—C31—C32—O7	177.8 (2)	O3—Co1—O2—C27	−2.70 (17)
C30—C31—C32—C33	−1.6 (3)	N1—Co1—O2—C27	−150.41 (18)
O7—C32—C33—C34	−176.2 (2)	N4ⁱ—Co1—O2—C27	104.81 (18)
C31—C32—C33—C34	3.3 (4)	O2—C27—O3—Co1	−5.1 (3)
C32—C33—C34—C29	−2.1 (4)	C21—C27—O3—Co1	172.6 (2)
C30—C29—C34—C33	−0.8 (3)	O6—Co1—O3—C27	178.96 (17)
C35—C29—C34—C33	177.2 (2)	N1—Co1—O3—C27	52.5 (2)
C30—C29—C35—O5	−6.7 (3)	N4ⁱ—Co1—O3—C27	−78.15 (18)
C34—C29—C35—O5	175.4 (2)	O2—Co1—O3—C27	2.69 (17)
C30—C29—C35—O6	172.9 (2)	C25—C24—O4—C28	−6.1 (3)
C34—C29—C35—O6	−5.0 (3)	C23—C24—O4—C28	174.7 (2)
N2—C7—N1—C6	0.4 (2)	O5—C35—O6—Co1	11.7 (3)
C8—C7—N1—C6	−177.3 (2)	C29—C35—O6—Co1	−167.95 (14)
N2—C7—N1—Co1	−178.13 (13)	O3—Co1—O6—C35	−84.34 (17)
C8—C7—N1—Co1	4.2 (3)	N1—Co1—O6—C35	60.66 (17)
C1—C6—N1—C7	−0.4 (2)	N4ⁱ—Co1—O6—C35	167.49 (16)
C5—C6—N1—C7	178.3 (2)	O2—Co1—O6—C35	−72.5 (3)
C1—C6—N1—Co1	178.14 (13)	C31—C32—O7—C36	−25.7 (3)
C5—C6—N1—Co1	−3.2 (3)	C33—C32—O7—C36	153.7 (2)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H015···O6ⁱ	0.93	2.46	3.111 (3)	127
C8—H8C···O2	0.96	2.50	3.255 (3)	136
C20—H03B···O2ⁱ	0.96	2.42	3.150 (3)	132

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Co₂(C₈H₇O₃)₄(C₂₀H₂₂N₄O)₂]
M_r	1391.24
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	12.4127 (3), 16.3933 (4), 17.6106 (5)
β (°)	109.577 (3)
V (Å³)	3376.34 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.56
Crystal size (mm)	0.32 × 0.28 × 0.24

Data collection
Diffractometer	Oxford Diffraction Gemini R Ultra CCD
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2006)
T_min, T_max	0.829, 0.889
No. of measured, independent and observed [I > 2σ(I)] reflections	14632, 7801, 3677
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.687

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.081, 0.75
No. of reflections	7801
No. of parameters	433
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.24

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Co1—O6	1.9694 (14)	Co1—N4ⁱ	2.0598 (18)
Co1—O3	2.0362 (18)	Co1—O2	2.374 (2)
Co1—N1	2.0524 (18)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H015···O6ⁱ	0.93	2.46	3.111 (3)	127
C8—H8C···O2	0.96	2.50	3.255 (3)	136
C20—H03B···O2ⁱ	0.96	2.42	3.150 (3)	132

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

The author thanks BoHai University for support.

References

Dimitrou, K., Brown, A.-D., Folting, K. & Christou, G. (1999). Inorg. Chem. 46, 7253–7255. Google Scholar
Hoskins, B. F., Robson, R. & Slizys, D. A. (1997). J. Am. Chem. Soc. 119, 2952–2953. CSD CrossRef CAS Web of Science Google Scholar
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS 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.

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