Crystal structure of poly[[μ-1,1′-(butane-1,4-di­yl)bis­(1H-benzimidazole)-κ2N3:N3′]{μ-4,4′-[1,4-phenyl­enebis(­oxy)]di­ben­zo­ato-κ4O,O′:O′′,O′′′}cobalt(II)]

Xie, C.; Zheng, C.G.

doi:10.1107/S2056989015008294

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 71| Part 6| June 2015| Pages m131-m132

doi:10.1107/S2056989015008294

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Crystal structure of poly[[μ-1,1′-(butane-1,4-diyl)bis(1H-benzimidazole)-κ²N³:N^3′]{μ-4,4′-[1,4-phenylenebis(oxy)]dibenzoato-κ⁴O,O′:O′′,O′′′}cobalt(II)]

Chen Xie ^a and ChangGe Zheng ^a ^*

^aSchool of Chemical and Material Engineering, Jiangnan University, 1800 Lihu Road, Wuxi, Jiangsu Province 214122, People's Republic of China
^*Correspondence e-mail: cgzheng@jiangnan.edu.cn

Edited by W. Imhof, University Koblenz-Landau, Germany (Received 4 April 2015; accepted 27 April 2015; online 20 May 2015)

In the title compound, [Co(C₂₀H₁₂O₆)(C₁₈H₁₈N₄)]_n, the Co^II atom, located on a twofold rotation axis, is hexacoordinated to four O from two bis-bidentate 4,4′-[phenylenebis(oxy)]dibenzoate (L) ligands and two N atoms from two 1,1′-(butane-1,4-diyl)bis(1H-benzimidazole) (bbbm) ligands, forming a distorted octahedral cis-N₂O₄ coordination environment. Polymeric zigzag chains along [102] are built up by the bridging L ligands. These chains are additionally connected by the bbbm ligands to produce a two-dimensional coordination polymer parallel too (010).

Keywords: crystal structure; metal–organic frameworks; bis-benzimidazole; dicarboxylate.

CCDC reference: 1045681

1. Related literature

As a result of their intriguing variety of architectures and topologies, metal–organic frameworks (MOFs) with transition metal Co have received extensive interest. Bis-benzimidazole ligands bearing with butyl spacers are a good choice for the assembly of versatile entangled structures, see: Liu et al. (2008 ). Complexes with dicarboxylate ligands represent the most reliable and typical building blocks which can be jointly applied to synthesize a wide range of compounds with coordination networks, see: Du et al. (2013 ). For the potential properties of metal–organic complexes involving polycarboxylate ligands or bis-benzimidazole, see: Li et al. (2011 ); Wang et al. (2004 ); Sun et al. (2009 ); Wang et al. (2005 ); Łyszczek & Mazur (2012 ); Meng et al. (2003 ).

2. Experimental

2.1. Crystal data

[Co(C₂₀H₁₂O₆)(C₁₈H₁₈N₄)]
M_r = 697.59
Monoclinic, C 2/c
a = 16.961 (4) Å
b = 16.446 (3) Å
c = 12.987 (3) Å
β = 117.022 (3)°
V = 3227.1 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.59 mm⁻¹
T = 296 K
0.27 × 0.24 × 0.19 mm

2.2. Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.858, T_max = 0.897
7207 measured reflections
2836 independent reflections
2385 reflections with I > 2σ(I)
R_int = 0.052

2.3. Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.140
S = 1.02
2836 reflections
222 parameters
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.65 e Å⁻³

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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: SHELXTL.

Supporting information

CCDC reference: 1045681

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S2056989015008294/im2463sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015008294/im2463Isup2.hkl

checkCIF report

Comment top

Because of the intriguing varieties of architectures and topologies, metal-organic frameworks (MOFs) with transition-metal Co have received extensive interests. The bis-benzimidazole ligands bearing with butyl spacers are a good choice for the assembly of versatile entangled structures. (Ying-Ying Liu et al., 2008) Complexes with the dicarboxylate ligands represent the most reliable and typical building blocks which can be jointly applied to synthesize a wide range of desired coordination networks (Du et al., 2013).

Single-crystal X-ray diffraction analyses reveal that Co(II) is six-coordinate. The asymmetric unit contains one Co(II) atom, a dicarboxylate ligand and a bbbm ligand. Two carboxylate groups adopt a chelating bidentate mode to connect one Co(II) atoms. The Co—O bond length is 2.3705 (24)Å (O1) and 2.0422 (21)Å (O2), the Co—N bond length is 2.0797 (26)Å.

Synthesis and crystallization top

A mixture of 1,4-bis(4-carboxylphenoxy)benzene (0.035 g, 0.1 mmol), 1,1'-(1,4-butyl) bis-benzimidazole (0.029 g, 0.1 mmol), Co(NO₃)₂ H₂O (0.029 g, 0.1 mmol), and deionized water (9 mL) was stired for 10 min at ambient temperature. Then the mixture was sealed in a Teflon-lined stainless vessel(25 mL) and heated at 160 °C for 3 days. The vessel was cooled to 50 °C by 9 °C decrease per hour, then cooled to ambient temperature directly. Amaranth transparent block-like crystal were obtained by fitretion and washed with deionized water. Yield: 34.2 mg(49 %, based on Co) Elemental analysis (%) calcd. for CoC₃₈H₃₀N₄O₆: C 65.33, H 4.3, N 8.02. Found: C 65.38, H 4.39, N 8.11.

Refinement top

The H atoms bonded to C atoms were introduced at calculated positions and refined using a riding model, with U_iso(H) = 1.2U_eq(C) and C–H distances of 0.93–0.97 Å.

Related literature top

As a result of their intriguing variety of architectures and topologies, metal–organic frameworks (MOFs) with transition metal Co have received extensive interest. Bis-benzimidazole ligands bearing with butyl spacers are a good choice for the assembly of versatile entangled structures, see: Liu et al. (2008). Complexes with dicarboxylate ligands represent the most reliable and typical building blocks which can be jointly applied to synthesize a wide range of desired coordination networks, see: Du et al. (2013). For the potential properties of metal–organic complexes involving polycarboxylate ligands or bis-benzimidazole, see: Li et al. (2011); Wang et al. (2004); Sun et al. (2009); Wang et al. (2005); Łyszczek & Mazur (2012); Meng et al. (2003).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of [Co(C₂₀H₁₂O₆)(C₁₈H₁₈N₄)]_n, with the non-H atom-numbering scheme and 30% probability displacement ellipsoids.
	Fig. 2. Three-dimensional network structure of [Co(C₂₀H₁₂O₆)(C₁₈H₁₈N₄)]_n formed by C—H–O interaction.

Poly[[µ-1,1'-(butane-1,4-diyl)bis(1H-benzimidazole)-κ²N³:N^3']{µ-4,4'-[1,4-phenylenebis(oxy)]dibenzoato-κ⁴O,O':O'',O'''}cobalt(II)] top

Crystal data top

[Co(C₂₀H₁₂O₆)(C₁₈H₁₈N₄)]	F(000) = 1444
M_r = 697.59	D_x = 1.436 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2720 reflections
a = 16.961 (4) Å	θ = 2.7–26.5°
b = 16.446 (3) Å	µ = 0.59 mm⁻¹
c = 12.987 (3) Å	T = 296 K
β = 117.022 (3)°	Block, purple
V = 3227.1 (12) Å³	0.27 × 0.24 × 0.19 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2836 independent reflections
Radiation source: fine-focus sealed tube	2385 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
phi and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −15→20
T_min = 0.858, T_max = 0.897	k = −17→19
7207 measured reflections	l = −14→15

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0857P)² + 2.0556P] where P = (F_o² + 2F_c²)/3
2836 reflections	(Δ/σ)_max < 0.001
222 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −0.65 e Å⁻³

Crystal data top

[Co(C₂₀H₁₂O₆)(C₁₈H₁₈N₄)]	V = 3227.1 (12) Å³
M_r = 697.59	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 16.961 (4) Å	µ = 0.59 mm⁻¹
b = 16.446 (3) Å	T = 296 K
c = 12.987 (3) Å	0.27 × 0.24 × 0.19 mm
β = 117.022 (3)°

Data collection top

Bruker APEXII CCD diffractometer	2836 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2385 reflections with I > 2σ(I)
T_min = 0.858, T_max = 0.897	R_int = 0.052
7207 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.02	Δρ_max = 0.61 e Å⁻³
2836 reflections	Δρ_min = −0.65 e Å⁻³
222 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	0.5000	0.10089 (3)	0.7500	0.0377 (2)
N1	0.46215 (15)	0.17924 (14)	0.84527 (17)	0.0426 (5)
O2	0.37200 (15)	0.07207 (16)	0.63915 (18)	0.0635 (6)
O1	0.46556 (13)	0.00024 (14)	0.60520 (19)	0.0591 (6)
N2	0.42235 (15)	0.21416 (15)	0.98059 (18)	0.0437 (5)
C16	0.36476 (17)	0.25422 (16)	0.8810 (2)	0.0424 (6)
C1	0.38817 (18)	0.02076 (17)	0.5798 (2)	0.0432 (6)
C2	0.31148 (17)	−0.01457 (15)	0.4757 (2)	0.0378 (6)
C3	0.32303 (18)	−0.03657 (17)	0.3804 (2)	0.0422 (6)
H3	0.3786	−0.0317	0.3830	0.051*
C17	0.47733 (18)	0.17001 (18)	0.9539 (2)	0.0438 (6)
H17	0.5214	0.1365	1.0064	0.053*
O3	0.10093 (17)	−0.10366 (14)	0.1800 (2)	0.0759 (8)
C11	0.39104 (18)	0.23265 (16)	0.7975 (2)	0.0417 (6)
C4	0.2531 (2)	−0.06546 (17)	0.2819 (2)	0.0477 (7)
H4	0.2610	−0.0801	0.2181	0.057*
C19	0.5047 (2)	0.2089 (2)	1.1943 (2)	0.0537 (7)
H19A	0.5404	0.2550	1.1945	0.064*
H19B	0.5351	0.1598	1.1908	0.064*
C7	0.22884 (19)	−0.0219 (2)	0.4712 (2)	0.0512 (7)
H7	0.2205	−0.0064	0.5344	0.061*
C13	0.2759 (2)	0.3149 (2)	0.6626 (3)	0.0696 (10)
H13	0.2448	0.3361	0.5885	0.084*
C8	0.05289 (18)	−0.04860 (18)	0.0917 (2)	0.0508 (7)
C10	0.0458 (2)	0.0333 (2)	0.1086 (2)	0.0576 (8)
H10	0.0771	0.0557	0.1819	0.069*
C5	0.1718 (2)	−0.07240 (18)	0.2787 (2)	0.0510 (7)
C12	0.3458 (2)	0.26448 (19)	0.6859 (3)	0.0572 (8)
H12	0.3628	0.2517	0.6291	0.069*
C18	0.4176 (2)	0.2131 (2)	1.0912 (2)	0.0584 (8)
H18A	0.3825	0.1667	1.0916	0.070*
H18B	0.3873	0.2618	1.0961	0.070*
C15	0.2935 (2)	0.30607 (19)	0.8577 (3)	0.0579 (8)
H15	0.2766	0.3200	0.9142	0.069*
C9	0.0075 (2)	−0.08197 (19)	−0.0168 (3)	0.0540 (8)
H9	0.0127	−0.1371	−0.0282	0.065*
C14	0.2497 (2)	0.3356 (2)	0.7465 (3)	0.0712 (10)
H14	0.2015	0.3700	0.7270	0.085*
C6	0.15846 (19)	−0.0521 (2)	0.3733 (3)	0.0591 (8)
H6	0.1032	−0.0586	0.3708	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0393 (3)	0.0508 (4)	0.0221 (3)	0.000	0.0133 (2)	0.000
N1	0.0524 (13)	0.0490 (13)	0.0281 (11)	0.0031 (10)	0.0198 (10)	−0.0016 (9)
O2	0.0606 (13)	0.0822 (16)	0.0457 (12)	−0.0111 (12)	0.0223 (10)	−0.0246 (11)
O1	0.0415 (11)	0.0632 (14)	0.0567 (13)	−0.0011 (10)	0.0083 (10)	−0.0031 (10)
N2	0.0495 (12)	0.0512 (14)	0.0342 (11)	−0.0018 (10)	0.0224 (10)	−0.0083 (10)
C16	0.0454 (14)	0.0390 (15)	0.0415 (14)	−0.0052 (12)	0.0185 (12)	−0.0062 (11)
C1	0.0465 (15)	0.0505 (16)	0.0281 (13)	0.0015 (12)	0.0130 (12)	0.0040 (11)
C2	0.0410 (13)	0.0369 (14)	0.0307 (13)	0.0026 (11)	0.0122 (11)	0.0039 (10)
C3	0.0439 (14)	0.0455 (15)	0.0342 (13)	0.0032 (12)	0.0152 (12)	0.0033 (11)
C17	0.0487 (15)	0.0527 (17)	0.0289 (13)	0.0023 (12)	0.0167 (11)	−0.0044 (11)
O3	0.0741 (16)	0.0512 (13)	0.0501 (13)	−0.0189 (11)	−0.0175 (12)	0.0059 (10)
C11	0.0491 (14)	0.0376 (14)	0.0340 (13)	−0.0043 (11)	0.0150 (12)	−0.0022 (10)
C4	0.0630 (18)	0.0448 (16)	0.0292 (13)	−0.0035 (14)	0.0155 (13)	0.0015 (11)
C19	0.0625 (18)	0.069 (2)	0.0373 (15)	−0.0063 (15)	0.0293 (14)	0.0003 (14)
C7	0.0501 (16)	0.065 (2)	0.0415 (15)	−0.0023 (14)	0.0236 (13)	−0.0036 (13)
C13	0.074 (2)	0.056 (2)	0.059 (2)	0.0119 (18)	0.0134 (18)	0.0121 (16)
C8	0.0381 (14)	0.0515 (18)	0.0407 (15)	−0.0122 (12)	−0.0016 (12)	0.0025 (12)
C10	0.0562 (17)	0.0547 (18)	0.0371 (15)	−0.0159 (15)	−0.0004 (13)	−0.0108 (13)
C5	0.0519 (16)	0.0420 (15)	0.0364 (15)	−0.0090 (13)	0.0001 (12)	0.0038 (12)
C12	0.0714 (19)	0.0513 (18)	0.0424 (16)	0.0000 (15)	0.0203 (15)	0.0041 (13)
C18	0.0693 (19)	0.076 (2)	0.0417 (16)	−0.0016 (17)	0.0352 (15)	−0.0120 (15)
C15	0.0546 (17)	0.0518 (18)	0.069 (2)	−0.0027 (14)	0.0294 (16)	−0.0109 (15)
C9	0.0506 (16)	0.0442 (16)	0.0478 (17)	−0.0096 (13)	0.0055 (14)	−0.0062 (13)
C14	0.0576 (19)	0.055 (2)	0.084 (3)	0.0104 (16)	0.0178 (19)	0.0052 (18)
C6	0.0381 (14)	0.068 (2)	0.064 (2)	−0.0069 (14)	0.0170 (14)	0.0044 (16)

Geometric parameters (Å, º) top

Co1—O2	2.042 (2)	C4—H4	0.9300
Co1—O2ⁱ	2.042 (2)	C19—C18	1.477 (4)
Co1—N1	2.080 (2)	C19—C19ⁱⁱ	1.526 (5)
Co1—N1ⁱ	2.080 (2)	C19—H19A	0.9700
Co1—O1	2.371 (2)	C19—H19B	0.9700
Co1—O1ⁱ	2.371 (2)	C7—C6	1.382 (4)
N1—C17	1.322 (3)	C7—H7	0.9300
N1—C11	1.390 (3)	C13—C12	1.363 (5)
O2—C1	1.255 (4)	C13—C14	1.392 (5)
O1—C1	1.246 (3)	C13—H13	0.9300
N2—C17	1.346 (3)	C8—C9	1.377 (4)
N2—C16	1.383 (4)	C8—C10	1.378 (5)
N2—C18	1.474 (3)	C10—C9ⁱⁱⁱ	1.378 (4)
C16—C15	1.395 (4)	C10—H10	0.9300
C16—C11	1.393 (4)	C5—C6	1.387 (4)
C1—C2	1.503 (4)	C12—H12	0.9300
C2—C7	1.381 (4)	C18—H18A	0.9700
C2—C3	1.387 (4)	C18—H18B	0.9700
C3—C4	1.375 (4)	C15—C14	1.378 (5)
C3—H3	0.9300	C15—H15	0.9300
C17—H17	0.9300	C9—C10ⁱⁱⁱ	1.378 (4)
O3—C8	1.396 (4)	C9—H9	0.9300
O3—C5	1.397 (3)	C14—H14	0.9300
C11—C12	1.398 (4)	C6—H6	0.9300
C4—C5	1.365 (4)

O2—Co1—O2ⁱ	153.16 (15)	C3—C4—H4	120.3
O2—Co1—N1	92.67 (9)	C18—C19—C19ⁱⁱ	111.6 (3)
O2ⁱ—Co1—N1	103.95 (9)	C18—C19—H19A	109.3
O2—Co1—N1ⁱ	103.95 (9)	C19ⁱⁱ—C19—H19A	109.3
O2ⁱ—Co1—N1ⁱ	92.67 (9)	C18—C19—H19B	109.3
N1—Co1—N1ⁱ	103.44 (13)	C19ⁱⁱ—C19—H19B	109.3
O2—Co1—O1	58.59 (8)	H19A—C19—H19B	108.0
O2ⁱ—Co1—O1	101.36 (9)	C2—C7—C6	120.4 (3)
N1—Co1—O1	150.83 (8)	C2—C7—H7	119.8
N1ⁱ—Co1—O1	89.54 (8)	C6—C7—H7	119.8
O2—Co1—O1ⁱ	101.36 (9)	C12—C13—C14	122.0 (3)
O2ⁱ—Co1—O1ⁱ	58.59 (8)	C12—C13—H13	119.0
N1—Co1—O1ⁱ	89.54 (8)	C14—C13—H13	119.0
N1ⁱ—Co1—O1ⁱ	150.83 (8)	C9—C8—C10	120.3 (3)
O1—Co1—O1ⁱ	91.42 (11)	C9—C8—O3	115.4 (3)
C17—N1—C11	104.9 (2)	C10—C8—O3	124.3 (3)
C17—N1—Co1	126.90 (19)	C9ⁱⁱⁱ—C10—C8	120.0 (3)
C11—N1—Co1	124.46 (17)	C9ⁱⁱⁱ—C10—H10	120.0
C1—O2—Co1	97.48 (18)	C8—C10—H10	120.0
C1—O1—Co1	82.61 (17)	C4—C5—C6	121.4 (3)
C17—N2—C16	107.1 (2)	C4—C5—O3	119.6 (3)
C17—N2—C18	126.5 (2)	C6—C5—O3	118.9 (3)
C16—N2—C18	126.1 (2)	C13—C12—C11	118.0 (3)
N2—C16—C15	131.9 (3)	C13—C12—H12	121.0
N2—C16—C11	105.5 (2)	C11—C12—H12	121.0
C15—C16—C11	122.6 (3)	N2—C18—C19	114.2 (2)
O1—C1—O2	121.2 (3)	N2—C18—H18A	108.7
O1—C1—C2	120.7 (2)	C19—C18—H18A	108.7
O2—C1—C2	118.1 (2)	N2—C18—H18B	108.7
C7—C2—C3	119.4 (2)	C19—C18—H18B	108.7
C7—C2—C1	121.3 (2)	H18A—C18—H18B	107.6
C3—C2—C1	119.2 (2)	C14—C15—C16	116.4 (3)
C4—C3—C2	120.5 (3)	C14—C15—H15	121.8
C4—C3—H3	119.7	C16—C15—H15	121.8
C2—C3—H3	119.7	C10ⁱⁱⁱ—C9—C8	119.7 (3)
N1—C17—N2	113.0 (2)	C10ⁱⁱⁱ—C9—H9	120.1
N1—C17—H17	123.5	C8—C9—H9	120.1
N2—C17—H17	123.5	C15—C14—C13	121.4 (3)
C8—O3—C5	116.9 (2)	C15—C14—H14	119.3
N1—C11—C16	109.5 (2)	C13—C14—H14	119.3
N1—C11—C12	131.0 (3)	C7—C6—C5	118.8 (3)
C16—C11—C12	119.5 (3)	C7—C6—H6	120.6
C5—C4—C3	119.4 (3)	C5—C6—H6	120.6
C5—C4—H4	120.3

O2—Co1—N1—C17	114.1 (2)	C16—N2—C17—N1	1.6 (3)
O2ⁱ—Co1—N1—C17	−44.6 (3)	C18—N2—C17—N1	175.4 (3)
N1ⁱ—Co1—N1—C17	−140.8 (3)	C17—N1—C11—C16	−0.2 (3)
O1—Co1—N1—C17	104.9 (3)	Co1—N1—C11—C16	159.27 (18)
O1ⁱ—Co1—N1—C17	12.8 (2)	C17—N1—C11—C12	−179.7 (3)
O2—Co1—N1—C11	−40.8 (2)	Co1—N1—C11—C12	−20.2 (4)
O2ⁱ—Co1—N1—C11	160.4 (2)	N2—C16—C11—N1	1.1 (3)
N1ⁱ—Co1—N1—C11	64.21 (19)	C15—C16—C11—N1	−178.7 (3)
O1—Co1—N1—C11	−50.1 (3)	N2—C16—C11—C12	−179.3 (2)
O1ⁱ—Co1—N1—C11	−142.2 (2)	C15—C16—C11—C12	0.9 (4)
O2ⁱ—Co1—O2—C1	−48.23 (18)	C2—C3—C4—C5	0.0 (4)
N1—Co1—O2—C1	−177.02 (19)	C3—C2—C7—C6	1.0 (4)
N1ⁱ—Co1—O2—C1	78.4 (2)	C1—C2—C7—C6	177.9 (3)
O1—Co1—O2—C1	−2.29 (17)	C5—O3—C8—C9	156.8 (3)
O1ⁱ—Co1—O2—C1	−86.95 (19)	C5—O3—C8—C10	−26.4 (5)
O2—Co1—O1—C1	2.31 (17)	C9—C8—C10—C9ⁱⁱⁱ	0.6 (6)
O2ⁱ—Co1—O1—C1	162.98 (16)	O3—C8—C10—C9ⁱⁱⁱ	−176.1 (3)
N1—Co1—O1—C1	13.2 (3)	C3—C4—C5—C6	−1.0 (4)
N1ⁱ—Co1—O1—C1	−104.39 (17)	C3—C4—C5—O3	−178.4 (2)
O1ⁱ—Co1—O1—C1	104.77 (18)	C8—O3—C5—C4	−86.4 (4)
C17—N2—C16—C15	178.2 (3)	C8—O3—C5—C6	96.1 (4)
C18—N2—C16—C15	4.4 (5)	C14—C13—C12—C11	0.6 (5)
C17—N2—C16—C11	−1.6 (3)	N1—C11—C12—C13	178.3 (3)
C18—N2—C16—C11	−175.4 (3)	C16—C11—C12—C13	−1.1 (4)
Co1—O1—C1—O2	−3.8 (3)	C17—N2—C18—C19	40.2 (4)
Co1—O1—C1—C2	175.3 (2)	C16—N2—C18—C19	−147.2 (3)
Co1—O2—C1—O1	4.4 (3)	C19ⁱⁱ—C19—C18—N2	179.41 (19)
Co1—O2—C1—C2	−174.77 (19)	N2—C16—C15—C14	−179.9 (3)
O1—C1—C2—C7	152.1 (3)	C11—C16—C15—C14	−0.1 (4)
O2—C1—C2—C7	−28.8 (4)	C10—C8—C9—C10ⁱⁱⁱ	−0.6 (6)
O1—C1—C2—C3	−31.1 (4)	O3—C8—C9—C10ⁱⁱⁱ	176.4 (3)
O2—C1—C2—C3	148.1 (3)	C16—C15—C14—C13	−0.4 (5)
C7—C2—C3—C4	0.0 (4)	C12—C13—C14—C15	0.2 (5)
C1—C2—C3—C4	−176.9 (2)	C2—C7—C6—C5	−2.0 (5)
C11—N1—C17—N2	−0.8 (3)	C4—C5—C6—C7	2.0 (5)
Co1—N1—C17—N2	−159.67 (18)	O3—C5—C6—C7	179.4 (3)

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1, y, −z+5/2; (iii) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	[Co(C₂₀H₁₂O₆)(C₁₈H₁₈N₄)]
M_r	697.59
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	16.961 (4), 16.446 (3), 12.987 (3)
β (°)	117.022 (3)
V (Å³)	3227.1 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.59
Crystal size (mm)	0.27 × 0.24 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.858, 0.897
No. of measured, independent and observed [I > 2σ(I)] reflections	7207, 2836, 2385
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.140, 1.02
No. of reflections	2836
No. of parameters	222
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.65

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authers thank NanJing University for the single-crystal X-ray diffraction determination.

References

Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Volume 71| Part 6| June 2015| Pages m131-m132

doi:10.1107/S2056989015008294

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