Poly[(μ2-4,4′-bipyridine-κ2N:N′)bis­(μ2-2-phen­oxy­propionato-κ2O:O′)cobalt(II)]

Shen, J.-B.; Liu, J.-L.; Zhao, G.-L.

doi:10.1107/S1600536811042875

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Pages m1587-m1588

doi:10.1107/S1600536811042875

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Poly[(μ₂-4,4′-bipyridine-κ²N:N′)bis(μ₂-2-phenoxypropionato-κ²O:O′)cobalt(II)]

Jin-Bei Shen,^a Jia-Lu Liu ^a and Guo-Liang Zhao ^a,^b ^*

^aCollege of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, Zhejiang, People's Republic of China, and ^bZhejiang Normal University Xingzhi College, Jinhua, Zhejiang 321004, People's Republic of China
^*Correspondence e-mail: sky53@zjnu.cn

(Received 29 September 2011; accepted 17 October 2011; online 22 October 2011)

In the polymeric title compound, [Co(C₉H₉O₃)₂(C₁₀H₈N₂)]_n, the Co^II ion is located on a twofold rotation axis and is six-coordinated by two N atoms from two 4,4′-bipyridine (4,4′-bipy) ligands in axial positions and by four O atoms from four 2-phenoxypropionate (POPA) anions in equatorial positions, defining a slightly distorted octahedral geometry. The carboxylate group of the POPA anion displays a bis-monodentate mode, linking pairs of Co^II ions into a chain parallel to [001]. Adjacent chains are connected in a perpendicular manner through 4,4′-bipy ligands into layers parallel to (100). The 4,4′-bipy ligand is likewise located on a twofold rotation axis, with a dihedral angle between the two pyridine rings of 57.05 (7)°. C—H⋯O hydrogen-bonding interactions are present within the layers. π–π stacking interactions between the POPA benzene rings of neighbouring layers [centroid-to-centroid distance = 3.976 (3) Å and plane-to-plane distance = 3.618 (3) Å] stabilize the packing of the structure.

Related literature

For background to phenoxyalkanoic acids, see: Müller & Buser (1997 ). For other metal complexes derived from phenoxypropionic acid, see: Shen et al. (2011a ,b ,c ,d ). For a related cobalt complex, see: Zhuang et al. (2007 ).

Experimental

Crystal data

[Co(C₉H₉O₃)₂(C₁₀H₈N₂)]
M_r = 545.44
Monoclinic, C 2/c
a = 23.6748 (14) Å
b = 11.6289 (7) Å
c = 9.6440 (6) Å
β = 96.353 (4)°
V = 2638.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.70 mm⁻¹
T = 296 K
0.41 × 0.20 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.847, T_max = 0.879
8421 measured reflections
2319 independent reflections
2053 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.068
S = 1.06
2319 reflections
170 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—O3	2.0357 (12)
Co1—O2ⁱ	2.1275 (11)
Co1—N1	2.1989 (19)
Co1—N2	2.2051 (19)
Symmetry code: (i) -x+1, -y+1, -z+2.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O2ⁱ	0.93	2.51	3.079 (2)	120
C15—H15A⋯O3ⁱ	0.93	2.38	3.272 (2)	159
Symmetry code: (i) -x+1, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811042875/wm2537sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811042875/wm2537Isup2.hkl

checkCIF report

Comment top

The group of phenoxyalkanoic acids include important herbicides. The desired biological activity is largely dependent on the length of the carbon chain of the alkanoic acid, the nature of the phenoxy group, and the position of its attachment to the carbon chain (Müller & Buser, 1997). Therefore the structures of metal complexes of 2-phenoxypropionic acid became interesting for us. Recently, we have reported some results in this regard (Shen et al., 2011a,b,c,d). Here, we describe a new Co^II complex with 4,4'-bipyridine (4,4'-bipy) as a co-ligand.

The structure of the polymeric title complex is shown in Fig. 1. The Co^II ion is located on a twofold rotation axis and is six-coordinated by four carboxylate O atoms from four POPA ligands and two N atoms of two 4,4'-bipy ligands in an octahedral geometry. The Co—O distances are 2.0357 (12) and 2.1275 (11) Å, and the Co—N distances are 2.1989 (19) and 2.2051 (19) Å, all of which are similar to related structures (Zhuang et al., 2007). The 4,4'-bipy ligand exhibits symmetry 2, with a dihedral angle between the two pyridine rings of 57.05 (7)°. The carboxylate groups of the POPA anions display a bis-monodentate mode, bridging pairs of Co^II ions into chains parallel to [001]. The 4,4'-bipy molecules connect these chains perpendicularly, resulting in a layered arrangement parallel to (100) (Fig. 2).

As also shown in Fig. 2, intra-layer C—H···O hydrogen bonds between the C atoms of 4,4'-bipy ligands and carboxylate O atoms are present. Adjacent layers are stacked along [100] through π—π interactions between benzene rings of the POPA anions, with centroid–centroid and plane to plane distance of 3.976 (3) Å and 3.618 (3) Å, respectively.

Related literature top

For background to phenoxyalkanoic acids, see: Müller & Buser (1997). For other metal complexes derived from phenoxypropionic acid, see: Shen et al. (2011a,b,c,d). For a related cobalt complex, see: Zhuang et al. (2007).

Experimental top

Reagents and solvents used were of commercially available quality and were not further purified before using. 2-Phenoxyproionic acid (0.332 g, 2 mmol), 4,4'-bipy (0.156 g, 1 mmol) were mixed in distilled water (30 ml), NaOH (1 M) was added dropwise to the solution to adjust a pH of 5–6, then CoCl₂.6H₂O (0.238 g, 1 mmol) was added and the mixture sealed in a 50 ml stainless steel reactor and kept at 433 K for 3 d. The reactor was then cooled to room temperature at a speed of 5 K h^-1. Red single crystals were obtained in high yield and filtered off from the solution.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. The molecular structure of the title complex, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. The atoms labelled with the suffix A, B, C, D, E, F, G are related by the symmetry operations (-x + 1, y, -z + 1.5), (-x + 1, -y + 1, -z + 2), (x, -y + 1, z - 1/2), (x, y + 1, z), (-x + 1, 1 + y, -z + 1.5), (x, y - 1, z), (-x + 1, y - 1, -z + 1.5), respectively.

Fig. 2. The layered arrangement of title compound, showing intralayer C—H···O interactions.

Poly[(µ₂-4,4'-bipyridine-κ²N:N')bis(µ₂-2- phenoxypropionato-κ²O:O')cobalt(II)] top

Crystal data top

[Co(C₉H₉O₃)₂(C₁₀H₈N₂)]	F(000) = 1132
M_r = 545.44	D_x = 1.373 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3897 reflections
a = 23.6748 (14) Å	θ = 1.7–25.0°
b = 11.6289 (7) Å	µ = 0.70 mm⁻¹
c = 9.6440 (6) Å	T = 296 K
β = 96.353 (4)°	Block, red
V = 2638.8 (3) Å³	0.41 × 0.20 × 0.19 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2319 independent reflections
Radiation source: fine-focus sealed tube	2053 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −28→26
T_min = 0.847, T_max = 0.879	k = −13→11
8421 measured reflections	l = −11→11

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.068	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0338P)² + 1.1007P] where P = (F_o² + 2F_c²)/3
2319 reflections	(Δ/σ)_max < 0.001
170 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

[Co(C₉H₉O₃)₂(C₁₀H₈N₂)]	V = 2638.8 (3) Å³
M_r = 545.44	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 23.6748 (14) Å	µ = 0.70 mm⁻¹
b = 11.6289 (7) Å	T = 296 K
c = 9.6440 (6) Å	0.41 × 0.20 × 0.19 mm
β = 96.353 (4)°

Data collection top

Bruker APEXII CCD diffractometer	2319 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2053 reflections with I > 2σ(I)
T_min = 0.847, T_max = 0.879	R_int = 0.023
8421 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.068	H-atom parameters constrained
S = 1.06	Δρ_max = 0.21 e Å⁻³
2319 reflections	Δρ_min = −0.19 e Å⁻³
170 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	0.52263 (3)	0.7500	0.02374 (11)
O3	0.55380 (5)	0.53098 (11)	0.92961 (11)	0.0393 (3)
C9	0.58754 (7)	0.49847 (13)	1.02991 (16)	0.0281 (4)
N1	0.5000	0.71171 (16)	0.7500	0.0290 (4)
C8	0.67426 (10)	0.6225 (2)	1.0358 (3)	0.0794 (8)
H8A	0.7136	0.6252	1.0199	0.119*
H8B	0.6708	0.6423	1.1312	0.119*
H8C	0.6530	0.6762	0.9751	0.119*
C7	0.65102 (8)	0.50059 (19)	1.0060 (2)	0.0493 (5)
H7	0.6548	0.4805	0.9088	0.059*
C11	0.45124 (8)	0.89365 (15)	0.76775 (19)	0.0384 (4)
H11	0.4177	0.9315	0.7812	0.046*
O1	0.68453 (5)	0.42260 (14)	1.09706 (14)	0.0555 (4)
C10	0.45282 (7)	0.77274 (15)	0.76537 (19)	0.0367 (4)
H10	0.4194	0.7328	0.7749	0.044*
C6	0.64660 (10)	0.2551 (2)	0.9605 (3)	0.0699 (7)
H6	0.6246	0.3010	0.8965	0.084*
C1	0.64664 (11)	0.1349 (3)	0.9439 (3)	0.0883 (9)
H1	0.6251	0.1027	0.8671	0.106*
C5	0.67937 (8)	0.3048 (2)	1.0721 (2)	0.0536 (6)
C4	0.71055 (10)	0.2322 (2)	1.1675 (2)	0.0651 (7)
H4	0.7324	0.2641	1.2440	0.078*
C3	0.70968 (11)	0.1124 (3)	1.1507 (3)	0.0810 (8)
H3	0.7308	0.0661	1.2158	0.097*
C2	0.67765 (12)	0.0629 (3)	1.0379 (4)	0.0906 (9)
H2	0.6770	−0.0164	1.0256	0.109*
C12	0.5000	0.95685 (19)	0.7500	0.0307 (5)
O2	0.57552 (5)	0.47394 (10)	1.14927 (11)	0.0339 (3)
C13	0.5000	0.08758 (19)	0.7500	0.0294 (5)
N2	0.5000	0.33300 (16)	0.7500	0.0311 (4)
C14	0.48321 (8)	0.15074 (14)	0.86106 (17)	0.0390 (4)
H14A	0.4708	0.1130	0.9371	0.047*
C15	0.48508 (8)	0.27175 (15)	0.85836 (17)	0.0380 (4)
H15A	0.4754	0.3115	0.9360	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.03125 (19)	0.01885 (18)	0.02070 (16)	0.000	0.00108 (12)	0.000
O3	0.0410 (7)	0.0518 (8)	0.0235 (6)	0.0044 (6)	−0.0037 (5)	−0.0006 (5)
C9	0.0328 (9)	0.0268 (10)	0.0250 (8)	−0.0021 (7)	0.0040 (7)	−0.0023 (6)
N1	0.0354 (11)	0.0228 (11)	0.0283 (10)	0.000	0.0020 (8)	0.000
C8	0.0486 (14)	0.088 (2)	0.1002 (19)	−0.0260 (13)	0.0020 (13)	0.0290 (16)
C7	0.0350 (11)	0.0761 (16)	0.0378 (10)	0.0012 (10)	0.0077 (8)	0.0059 (10)
C11	0.0383 (10)	0.0266 (10)	0.0519 (10)	0.0060 (8)	0.0123 (8)	0.0033 (8)
O1	0.0366 (8)	0.0757 (11)	0.0525 (8)	0.0119 (7)	−0.0024 (6)	−0.0041 (8)
C10	0.0350 (10)	0.0263 (10)	0.0497 (10)	−0.0025 (8)	0.0088 (8)	0.0017 (8)
C6	0.0475 (14)	0.096 (2)	0.0644 (15)	0.0133 (13)	0.0001 (11)	−0.0174 (14)
C1	0.0584 (17)	0.102 (2)	0.103 (2)	0.0051 (16)	0.0024 (15)	−0.0423 (19)
C5	0.0315 (10)	0.0771 (17)	0.0535 (12)	0.0076 (10)	0.0104 (9)	−0.0093 (11)
C4	0.0461 (13)	0.086 (2)	0.0623 (14)	0.0115 (12)	0.0026 (11)	−0.0031 (13)
C3	0.0592 (16)	0.084 (2)	0.101 (2)	0.0153 (15)	0.0129 (15)	0.0090 (17)
C2	0.0567 (17)	0.079 (2)	0.139 (3)	0.0018 (16)	0.0263 (18)	−0.024 (2)
C12	0.0462 (15)	0.0207 (14)	0.0255 (11)	0.000	0.0046 (10)	0.000
O2	0.0351 (7)	0.0398 (7)	0.0276 (6)	0.0029 (5)	0.0070 (5)	0.0071 (5)
C13	0.0388 (14)	0.0197 (13)	0.0294 (11)	0.000	0.0022 (10)	0.000
N2	0.0419 (12)	0.0229 (11)	0.0282 (10)	0.000	0.0019 (9)	0.000
C14	0.0627 (12)	0.0250 (10)	0.0312 (9)	0.0026 (9)	0.0133 (8)	0.0049 (7)
C15	0.0605 (12)	0.0258 (10)	0.0292 (8)	0.0051 (9)	0.0119 (8)	−0.0018 (7)

Geometric parameters (Å, º) top

Co1—O3ⁱ	2.0357 (12)	C6—C5	1.382 (3)
Co1—O3	2.0357 (12)	C6—C1	1.407 (4)
Co1—O2ⁱⁱ	2.1275 (11)	C6—H6	0.9300
Co1—O2ⁱⁱⁱ	2.1275 (11)	C1—C2	1.384 (4)
Co1—N1	2.1989 (19)	C1—H1	0.9300
Co1—N2	2.2051 (19)	C5—C4	1.398 (3)
O3—C9	1.243 (2)	C4—C3	1.402 (4)
C9—O2	1.2489 (18)	C4—H4	0.9300
C9—C7	1.546 (2)	C3—C2	1.381 (4)
N1—C10	1.3453 (19)	C3—H3	0.9300
N1—C10ⁱ	1.3453 (19)	C2—H2	0.9300
C8—C7	1.537 (3)	C12—C11ⁱ	1.395 (2)
C8—H8A	0.9600	C12—C13^iv	1.520 (3)
C8—H8B	0.9600	O2—Co1ⁱⁱⁱ	2.1275 (11)
C8—H8C	0.9600	C13—C14	1.3924 (19)
C7—O1	1.438 (2)	C13—C14ⁱ	1.392 (2)
C7—H7	0.9800	C13—C12^v	1.520 (3)
C11—C12	1.395 (2)	N2—C15ⁱ	1.3439 (19)
C11—C10	1.407 (2)	N2—C15	1.3439 (19)
C11—H11	0.9300	C14—C15	1.408 (2)
O1—C5	1.394 (3)	C14—H14A	0.9300
C10—H10	0.9300	C15—H15A	0.9300

O3ⁱ—Co1—O3	174.53 (7)	N1—C10—C11	123.57 (16)
O3ⁱ—Co1—O2ⁱⁱ	95.10 (5)	N1—C10—H10	118.2
O3—Co1—O2ⁱⁱ	84.80 (5)	C11—C10—H10	118.2
O3ⁱ—Co1—O2ⁱⁱⁱ	84.80 (5)	C5—C6—C1	119.8 (3)
O3—Co1—O2ⁱⁱⁱ	95.10 (5)	C5—C6—H6	120.1
O2ⁱⁱ—Co1—O2ⁱⁱⁱ	177.85 (6)	C1—C6—H6	120.1
O3ⁱ—Co1—N1	87.26 (4)	C2—C1—C6	122.3 (3)
O3—Co1—N1	87.26 (4)	C2—C1—H1	118.9
O2ⁱⁱ—Co1—N1	88.93 (3)	C6—C1—H1	118.9
O2ⁱⁱⁱ—Co1—N1	88.93 (3)	C6—C5—O1	125.2 (2)
O3ⁱ—Co1—N2	92.74 (4)	C6—C5—C4	118.1 (2)
O3—Co1—N2	92.74 (4)	O1—C5—C4	116.7 (2)
O2ⁱⁱ—Co1—N2	91.07 (3)	C5—C4—C3	121.6 (2)
O2ⁱⁱⁱ—Co1—N2	91.07 (3)	C5—C4—H4	119.2
N1—Co1—N2	180.0	C3—C4—H4	119.2
C9—O3—Co1	159.26 (12)	C2—C3—C4	120.4 (3)
O3—C9—O2	126.46 (16)	C2—C3—H3	119.8
O3—C9—C7	115.51 (14)	C4—C3—H3	119.8
O2—C9—C7	117.75 (15)	C3—C2—C1	118.0 (3)
C10—N1—C10ⁱ	116.3 (2)	C3—C2—H2	121.0
C10—N1—Co1	121.84 (10)	C1—C2—H2	121.0
C10ⁱ—N1—Co1	121.84 (10)	C11—C12—C11ⁱ	116.4 (2)
C7—C8—H8A	109.5	C11—C12—C13^iv	121.80 (10)
C7—C8—H8B	109.5	C11ⁱ—C12—C13^iv	121.80 (10)
H8A—C8—H8B	109.5	C9—O2—Co1ⁱⁱⁱ	134.85 (11)
C7—C8—H8C	109.5	C14—C13—C14ⁱ	116.3 (2)
H8A—C8—H8C	109.5	C14—C13—C12^v	121.84 (10)
H8B—C8—H8C	109.5	C14ⁱ—C13—C12^v	121.84 (10)
O1—C7—C8	107.80 (18)	C15ⁱ—N2—C15	116.0 (2)
O1—C7—C9	112.24 (15)	C15ⁱ—N2—Co1	122.01 (10)
C8—C7—C9	108.70 (17)	C15—N2—Co1	122.01 (10)
O1—C7—H7	109.4	C13—C14—C15	120.04 (15)
C8—C7—H7	109.4	C13—C14—H14A	120.0
C9—C7—H7	109.4	C15—C14—H14A	120.0
C12—C11—C10	120.05 (16)	N2—C15—C14	123.75 (15)
C12—C11—H11	120.0	N2—C15—H15A	118.1
C10—C11—H11	120.0	C14—C15—H15A	118.1
C5—O1—C7	118.84 (16)

O2ⁱⁱ—Co1—O3—C9	−81.2 (3)	C1—C6—C5—C4	−1.7 (3)
O2ⁱⁱⁱ—Co1—O3—C9	101.0 (3)	C7—O1—C5—C6	4.0 (3)
N1—Co1—O3—C9	−170.3 (3)	C7—O1—C5—C4	−176.79 (16)
N2—Co1—O3—C9	9.7 (3)	C6—C5—C4—C3	0.9 (3)
Co1—O3—C9—O2	−96.6 (3)	O1—C5—C4—C3	−178.37 (19)
Co1—O3—C9—C7	89.7 (3)	C5—C4—C3—C2	0.1 (4)
O3ⁱ—Co1—N1—C10	65.25 (10)	C4—C3—C2—C1	−0.3 (4)
O3—Co1—N1—C10	−114.75 (10)	C6—C1—C2—C3	−0.4 (4)
O2ⁱⁱ—Co1—N1—C10	160.41 (10)	C10—C11—C12—C11ⁱ	−0.79 (12)
O2ⁱⁱⁱ—Co1—N1—C10	−19.59 (10)	C10—C11—C12—C13^iv	179.21 (12)
O3ⁱ—Co1—N1—C10ⁱ	−114.75 (10)	O3—C9—O2—Co1ⁱⁱⁱ	−2.7 (3)
O3—Co1—N1—C10ⁱ	65.25 (10)	C7—C9—O2—Co1ⁱⁱⁱ	170.92 (12)
O2ⁱⁱ—Co1—N1—C10ⁱ	−19.59 (10)	O3ⁱ—Co1—N2—C15ⁱ	56.44 (11)
O2ⁱⁱⁱ—Co1—N1—C10ⁱ	160.41 (10)	O3—Co1—N2—C15ⁱ	−123.56 (11)
O3—C9—C7—O1	−156.70 (16)	O2ⁱⁱ—Co1—N2—C15ⁱ	−38.72 (10)
O2—C9—C7—O1	29.0 (2)	O2ⁱⁱⁱ—Co1—N2—C15ⁱ	141.28 (10)
O3—C9—C7—C8	84.2 (2)	O3ⁱ—Co1—N2—C15	−123.56 (11)
O2—C9—C7—C8	−90.2 (2)	O3—Co1—N2—C15	56.44 (11)
C8—C7—O1—C5	−167.58 (16)	O2ⁱⁱ—Co1—N2—C15	141.28 (11)
C9—C7—O1—C5	72.7 (2)	O2ⁱⁱⁱ—Co1—N2—C15	−38.72 (11)
C10ⁱ—N1—C10—C11	−0.85 (13)	C14ⁱ—C13—C14—C15	−1.47 (13)
Co1—N1—C10—C11	179.15 (13)	C12^v—C13—C14—C15	178.53 (13)
C12—C11—C10—N1	1.7 (3)	C15ⁱ—N2—C15—C14	−1.59 (14)
C5—C6—C1—C2	1.5 (4)	Co1—N2—C15—C14	178.41 (14)
C1—C6—C5—O1	177.6 (2)	C13—C14—C15—N2	3.2 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2ⁱⁱⁱ	0.93	2.51	3.079 (2)	120
C15—H15A···O3ⁱⁱⁱ	0.93	2.38	3.272 (2)	159

Symmetry code: (iii) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	[Co(C₉H₉O₃)₂(C₁₀H₈N₂)]
M_r	545.44
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	23.6748 (14), 11.6289 (7), 9.6440 (6)
β (°)	96.353 (4)
V (Å³)	2638.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.70
Crystal size (mm)	0.41 × 0.20 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.847, 0.879
No. of measured, independent and observed [I > 2σ(I)] reflections	8421, 2319, 2053
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.068, 1.06
No. of reflections	2319
No. of parameters	170
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.19

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Co1—O3	2.0357 (12)	Co1—N1	2.1989 (19)
Co1—O2ⁱ	2.1275 (11)	Co1—N2	2.2051 (19)

Symmetry code: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2ⁱ	0.93	2.51	3.079 (2)	119.5
C15—H15A···O3ⁱ	0.93	2.38	3.272 (2)	158.8

Symmetry code: (i) −x+1, −y+1, −z+2.

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Müller, M. D. & Buser, H. R. (1997). Environ. Sci. Technol. 31, 1953–1959. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shen, J.-B., Liu, J.-L. & Zhao, G.-L. (2011a). Acta Cryst. E67, m1234. Web of Science CSD CrossRef IUCr Journals Google Scholar
Shen, J.-B., Liu, J.-L. & Zhao, G.-L. (2011b). Acta Cryst. E67, m1319. Web of Science CSD CrossRef IUCr Journals Google Scholar
Shen, J.-B., Liu, J.-L. & Zhao, G.-L. (2011c). Acta Cryst. E67, m1320. Web of Science CSD CrossRef IUCr Journals Google Scholar
Shen, J.-B., Liu, J.-L. & Zhao, G.-L. (2011d). Acta Cryst. E67, m1321. Web of Science CSD CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhuang, W.-J., Zheng, X.-J., Li, L.-C., Liao, D.-Z., Ma, H. & Jin, L.-P. (2007). CrystEngComm, 9, 653–667. Web of Science CSD CrossRef CAS Google Scholar

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Volume 67| Part 11| November 2011| Pages m1587-m1588

doi:10.1107/S1600536811042875

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