Poly[(μ3-5-amino­isophthalato-κ4O,O′:O′′:O′′′)[μ2-1,2-bis­(4-pyrid­yl)ethane-κ2N:N′]cobalt(II)]

Lush, S.F.; Shen, F.M.

doi:10.1107/S1600536810030710

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Pages m1069-m1070

https://doi.org/10.1107/S1600536810030710

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Poly[(μ₃-5-aminoisophthalato-κ⁴O,O′:O′′:O′′′)[μ₂-1,2-bis(4-pyridyl)ethane-κ²N:N′]cobalt(II)]

Shie Fu Lush ^a and Fwu Ming Shen ^b ^*

^aGeneral Education Center, Yuanpei University, Hsinchu 30015, Taiwan, and ^bDepartment of Biotechnology, Yuanpei University, No. 306, Yuanpei St., Hsinchu 30015, Taiwan
^*Correspondence e-mail: fmshen@mail.ypu.edu.tw

(Received 26 July 2010; accepted 2 August 2010; online 11 August 2010)

In the title compound, [Co(C₈H₅NO₄)(C₁₂H₁₂N₂)]_n, the Co^II ion presents a distorted CoO₄N₂ octahedral coordination geometry, formed by three 5-aminoisophthalate dianions and two 1,2-bis(4-pyridyl)ethane ligands. One carboxylate group of the 5-aminoisophthalate dianion chelates a Co cation and the other carboxylate group bridges the other two Co cations, while the terminal N atoms of the 1,2-bis(4-pyridyl)ethane ligand coordinate the neighboring Co cations, forming a two-dimensional polymeric architecture. Two pyridine rings of the 1,2-bis(4-pyridyl)ethane ligand are twisted to each other with a dihedral angle of 50.94 (16)°. Weak C—H⋯O hydrogen bonding and N—H⋯π interactions are observed in the crystal structure. A void of 69 (5) Å³ is present in the crystal structure, but no solvent molecule can be located reasonably.

Related literature

For similar polymeric structures, see: He et al. (2006 ); Tang et al. (2007 ); Zhang et al. (2007 ); Ou et al. (2008 ); Zhang et al. (2009 ).

Experimental

Crystal data

[Co(C₈H₅NO₄)(C₁₂H₁₂N₂)]
M_r = 422.30
Triclinic, $[P \overline 1]$
a = 9.9093 (2) Å
b = 10.0755 (2) Å
c = 10.5065 (3) Å
α = 78.301 (1)°
β = 83.560 (1)°
γ = 68.074 (2)°
V = 952.12 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.93 mm⁻¹
T = 298 K
0.22 × 0.18 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ) T_min = 0.732, T_max = 0.840
7715 measured reflections
3356 independent reflections
3003 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.120
S = 1.16
3356 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—N1	2.178 (2)
Co1—N2ⁱ	2.175 (3)
Co1—O1	2.0416 (18)
Co1—O2ⁱⁱ	2.011 (2)
Co1—O3ⁱⁱⁱ	2.1426 (19)
Co1—O4ⁱⁱⁱ	2.228 (2)
Symmetry codes: (i) x-1, y, z+1; (ii) -x, -y+1, -z+1; (iii) x, y-1, z.

Table 2
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the N1-pyridine ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O4^iv	0.93	2.35	3.271 (4)	173
C10—H10⋯O2^v	0.93	2.44	3.276 (5)	150
C15—H15⋯O3^vi	0.93	2.56	3.487 (4)	175
N3—H3A⋯Cg4^vii	0.86	2.92	3.765 (3)	169
Symmetry codes: (iv) -x, -y+2, -z; (v) x+1, y, z-1; (vi) -x, -y+2, -z+1; (vii) -x, -y+1, -z.

Data collection: COLLECT (Nonius, 2000 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810030710/xu5004sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810030710/xu5004Isup2.hkl

checkCIF report

Comment top

In recent years, we have been focused on organic-inorganic hybrid material containing either N– or O-donor rigid heteroaromatic ligands, such as 5-Aminoisophthalic acid (aip). The polycarboxylic acid ligands can bridge one or more metal centers and produce neutral architectures. Hence, metal-organic coordination polymers constructed by mixed ligands of pyridyl and carboxylate groups not only incorporate interesting propertied of different functional groups but also are more adjustable through changing one of the mixing organic ligands. However, few coordination polymers based on amino aromatic di or poly(carboxylic acids) ligands and bipyridine has been reported (He et al. 2006; Tang et al. 2007; Zhang et al. 2007; Ou et al. 2008; Zhang et al. 2009).

The title compound by X-ray crystallography reveals that the symmetric unit consist of one Co^II ion, two 1,2-bis(4-pyridyl)ethane (dpe) ligands and three aip ligands, as shown in Fig. 1. The Co^II ion is six-coordinated with a slightly distorted octahedral geometry. The equatorial plane is occupied by two monodentate carboxylate oxygen atoms from two aip ligands and one bidentate carboxylate oxygen atoms from one aip ligand, while the axial sites are occupied by two nitrogen atoms of the pyridine groups from two dpe ligands (Table 1). Each aip ligand employs its two carboxylate groups in turn to coordinate to three metal centers, while the remains amino group in uncoordinated manner. The four symmetry-related metal centers are linked by two aip ligands and two dpe ligands to form a 30-membered macro cycle with Co···Co separation of 6.956 (3) Å and 13.610 (8) Å, respectively, showing 1-D open channels along the crystallographic c axis. In title polymer, there are no classical hydrogen bonding interactions, but C—H···O hydrogen-bonding is observed in the crystal structure (Table 2).

In addition, C—H···π interactions C11—H11···Cg3 (N1/C2—C5), N—H···π interactions N3—H···Cg4 (N2/C8—C12) are present in the crystal structure (full details and symmetry codes are given in Table 2). π···π stacking interactions are also observed, the centroid-centroid between Cg3(O3—O4/C17/Co1c)···Cg4^vii(N1/C1—C5), Cg3···Cg5(N2/C8—C12)^viii are 3.8307 (17) and 3.9143 (18) [symmetry codes: (vii)= X, 1+Y, Z, (viii)= 1-X,1-Y,-Z.], respectively.

Related literature top

For similar polymeric structures, see: He et al. (2006); Tang et al. (2007); Zhang et al. (2007); Ou et al. (2008); Zhang et al. (2009).

Experimental top

CoBr₂ (0.1097 g, 0.5 mmol), 5-aminoisophthalic acid, (0.0903 g, 0.5 mmol) and 1,2-bis(4-pyridyl)ethane (0.0913 g, 0.5 mmol) were mixed in 10 ml deionized water. After being stirred for 30 min, the mixture was placed in a 25 ml Teflon liner reactor and heated at 423 K in the oven for 24 h. The resulting solution was slowly cooled to room temperature. The purple transparent single crystals of the title compound were obtained in 46.45% yield (based on cobalt).

Structure description top

For similar polymeric structures, see: He et al. (2006); Tang et al. (2007); Zhang et al. (2007); Ou et al. (2008); Zhang et al. (2009).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

Fig. 1. View of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.

Poly[(µ₃-5-aminoisophthalato- κ⁴O,O':O'':O''')[µ₂-1,2-bis(4- pyridyl)ethane-κ²N:N']cobalt(II)] top

Crystal data top

[Co(C₈H₅NO₄)(C₁₂H₁₂N₂)]	Z = 2
M_r = 422.30	F(000) = 434
Triclinic, P1	D_x = 1.473 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9093 (2) Å	Cell parameters from 6854 reflections
b = 10.0755 (2) Å	θ = 2.0–25.0°
c = 10.5065 (3) Å	µ = 0.93 mm⁻¹
α = 78.301 (1)°	T = 298 K
β = 83.560 (1)°	Prism, purple
γ = 68.074 (2)°	0.22 × 0.18 × 0.08 mm
V = 952.12 (4) Å³

Data collection top

Nonius KappaCCD diffractometer	3356 independent reflections
Radiation source: fine-focus sealed tube	3003 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
Detector resolution: 9 pixels mm^-1	θ_max = 25.0°, θ_min = 2.2°
ω/2θ scans	h = −11→11
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −11→11
T_min = 0.732, T_max = 0.840	l = −12→12
7715 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.16	w = 1/[σ²(F_o²) + (0.0694P)² + 0.2452P] where P = (F_o² + 2F_c²)/3
3356 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.60 e Å⁻³

Crystal data top

[Co(C₈H₅NO₄)(C₁₂H₁₂N₂)]	γ = 68.074 (2)°
M_r = 422.30	V = 952.12 (4) Å³
Triclinic, P1	Z = 2
a = 9.9093 (2) Å	Mo Kα radiation
b = 10.0755 (2) Å	µ = 0.93 mm⁻¹
c = 10.5065 (3) Å	T = 298 K
α = 78.301 (1)°	0.22 × 0.18 × 0.08 mm
β = 83.560 (1)°

Data collection top

Nonius KappaCCD diffractometer	3356 independent reflections
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	3003 reflections with I > 2σ(I)
T_min = 0.732, T_max = 0.840	R_int = 0.038
7715 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 1.16	Δρ_max = 0.58 e Å⁻³
3356 reflections	Δρ_min = −0.60 e Å⁻³
253 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	−0.03642 (4)	0.35863 (3)	0.37674 (3)	0.0234 (1)
O1	−0.1184 (2)	0.57793 (18)	0.31360 (18)	0.0285 (6)
O2	−0.0962 (2)	0.6739 (2)	0.47933 (18)	0.0323 (6)
O3	0.0094 (2)	1.1365 (2)	0.36324 (18)	0.0308 (6)
O4	−0.1437 (2)	1.3060 (2)	0.2285 (2)	0.0359 (6)
N1	0.1467 (2)	0.3521 (2)	0.2393 (2)	0.0279 (7)
N2	0.7840 (3)	0.3556 (3)	−0.4846 (2)	0.0317 (7)
N3	−0.2170 (3)	0.9890 (3)	−0.0716 (2)	0.0406 (9)
C1	0.2784 (3)	0.2469 (3)	0.2530 (3)	0.0358 (9)
C2	0.3902 (3)	0.2352 (3)	0.1606 (3)	0.0395 (9)
C3	0.3706 (3)	0.3366 (3)	0.0468 (3)	0.0355 (9)
C4	0.2349 (3)	0.4469 (4)	0.0337 (3)	0.0423 (10)
C5	0.1282 (3)	0.4506 (3)	0.1293 (3)	0.0381 (9)
C6	0.4901 (3)	0.3287 (4)	−0.0575 (3)	0.0493 (10)
C7	0.4432 (4)	0.3491 (5)	−0.1921 (3)	0.0622 (16)
C8	0.5608 (3)	0.3512 (4)	−0.2951 (3)	0.0434 (10)
C9	0.5940 (4)	0.4743 (4)	−0.3398 (4)	0.0577 (12)
C10	0.7050 (4)	0.4714 (4)	−0.4323 (3)	0.0490 (11)
C11	0.7517 (3)	0.2363 (3)	−0.4412 (3)	0.0435 (10)
C12	0.6425 (4)	0.2314 (4)	−0.3494 (3)	0.0491 (11)
C13	−0.1119 (3)	0.6807 (3)	0.3616 (3)	0.0247 (8)
C14	−0.1282 (3)	0.8214 (3)	0.2696 (3)	0.0252 (8)
C15	−0.1013 (3)	0.9306 (3)	0.3130 (3)	0.0269 (8)
C16	−0.1136 (3)	1.0592 (3)	0.2279 (3)	0.0266 (8)
C17	−0.0809 (3)	1.1747 (3)	0.2751 (3)	0.0267 (8)
C18	−0.1542 (3)	1.0802 (3)	0.1017 (3)	0.0295 (8)
C19	−0.1780 (3)	0.9694 (3)	0.0556 (3)	0.0289 (8)
C20	−0.1643 (3)	0.8411 (3)	0.1413 (3)	0.0274 (8)
H1	0.29510	0.17810	0.32900	0.0430*
H2	0.47920	0.15920	0.17450	0.0470*
H3A	−0.23300	0.92110	−0.09820	0.0490*
H3B	−0.22510	1.06900	−0.12380	0.0490*
H4	0.21640	0.51860	−0.04030	0.0510*
H5	0.03820	0.52540	0.11730	0.0460*
H6A	0.52950	0.40260	−0.05370	0.0590*
H6B	0.56780	0.23490	−0.03870	0.0590*
H7A	0.36110	0.43990	−0.20910	0.0750*
H7B	0.41040	0.27120	−0.19800	0.0750*
H9	0.54140	0.55930	−0.30760	0.0690*
H10	0.72570	0.55580	−0.45960	0.0590*
H11	0.80580	0.15250	−0.47470	0.0520*
H12	0.62370	0.14580	−0.32390	0.0590*
H15	−0.07540	0.91760	0.39830	0.0320*
H18	−0.16590	1.16830	0.04670	0.0350*
H20	−0.17950	0.76670	0.11240	0.0330*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0327 (2)	0.0192 (2)	0.0210 (2)	−0.0133 (2)	0.0040 (2)	−0.0048 (2)
O1	0.0409 (10)	0.0202 (9)	0.0278 (10)	−0.0143 (8)	−0.0001 (8)	−0.0062 (8)
O2	0.0487 (11)	0.0302 (11)	0.0229 (10)	−0.0211 (9)	−0.0035 (9)	−0.0009 (8)
O3	0.0425 (11)	0.0253 (10)	0.0294 (10)	−0.0169 (8)	−0.0038 (9)	−0.0052 (8)
O4	0.0529 (12)	0.0208 (10)	0.0365 (11)	−0.0157 (9)	−0.0079 (10)	−0.0025 (8)
N1	0.0343 (12)	0.0288 (12)	0.0216 (11)	−0.0134 (10)	0.0039 (9)	−0.0057 (9)
N2	0.0359 (12)	0.0333 (13)	0.0279 (12)	−0.0167 (10)	0.0082 (10)	−0.0067 (10)
N3	0.0644 (17)	0.0355 (14)	0.0287 (13)	−0.0250 (13)	−0.0137 (12)	−0.0003 (11)
C1	0.0415 (16)	0.0321 (16)	0.0280 (15)	−0.0108 (13)	0.0031 (13)	0.0001 (12)
C2	0.0342 (15)	0.0410 (17)	0.0355 (17)	−0.0062 (13)	0.0022 (13)	−0.0059 (14)
C3	0.0336 (15)	0.0454 (18)	0.0281 (15)	−0.0158 (13)	0.0058 (12)	−0.0088 (13)
C4	0.0431 (17)	0.0459 (18)	0.0262 (15)	−0.0104 (14)	0.0074 (13)	0.0040 (13)
C5	0.0336 (15)	0.0386 (17)	0.0305 (16)	−0.0043 (12)	0.0056 (12)	−0.0011 (13)
C6	0.0356 (16)	0.072 (2)	0.0366 (18)	−0.0191 (16)	0.0097 (14)	−0.0081 (16)
C7	0.0402 (18)	0.116 (4)	0.0359 (19)	−0.037 (2)	0.0131 (15)	−0.016 (2)
C8	0.0347 (15)	0.071 (2)	0.0256 (15)	−0.0241 (16)	0.0068 (13)	−0.0057 (15)
C9	0.063 (2)	0.062 (2)	0.054 (2)	−0.0273 (19)	0.0290 (18)	−0.0309 (19)
C10	0.060 (2)	0.0447 (19)	0.053 (2)	−0.0313 (16)	0.0259 (17)	−0.0232 (16)
C11	0.0495 (18)	0.0369 (17)	0.0438 (19)	−0.0200 (14)	0.0148 (15)	−0.0068 (14)
C12	0.0530 (19)	0.049 (2)	0.046 (2)	−0.0283 (16)	0.0121 (16)	0.0020 (16)
C13	0.0282 (12)	0.0216 (13)	0.0252 (14)	−0.0116 (10)	0.0023 (10)	−0.0031 (11)
C14	0.0314 (13)	0.0192 (13)	0.0269 (14)	−0.0122 (10)	0.0006 (11)	−0.0029 (10)
C15	0.0379 (14)	0.0213 (13)	0.0231 (13)	−0.0121 (11)	−0.0015 (11)	−0.0044 (10)
C16	0.0344 (13)	0.0210 (13)	0.0269 (14)	−0.0128 (11)	0.0012 (11)	−0.0057 (11)
C17	0.0367 (14)	0.0243 (14)	0.0215 (13)	−0.0157 (11)	0.0054 (11)	−0.0039 (11)
C18	0.0387 (14)	0.0219 (14)	0.0272 (14)	−0.0118 (11)	−0.0013 (12)	−0.0011 (11)
C19	0.0350 (14)	0.0285 (14)	0.0255 (14)	−0.0141 (11)	−0.0034 (11)	−0.0032 (11)
C20	0.0357 (14)	0.0234 (13)	0.0281 (14)	−0.0141 (11)	−0.0020 (12)	−0.0082 (11)

Geometric parameters (Å, º) top

Co1—N1	2.178 (2)	C9—C10	1.380 (6)
Co1—N2ⁱ	2.175 (3)	C11—C12	1.375 (5)
Co1—O1	2.0416 (18)	C13—C14	1.509 (4)
Co1—O2ⁱⁱ	2.011 (2)	C14—C20	1.390 (4)
Co1—O3ⁱⁱⁱ	2.1426 (19)	C14—C15	1.393 (4)
Co1—O4ⁱⁱⁱ	2.228 (2)	C15—C16	1.389 (4)
O1—C13	1.265 (3)	C16—C17	1.502 (4)
O2—C13	1.249 (4)	C16—C18	1.381 (4)
O3—C17	1.261 (4)	C18—C19	1.406 (4)
O4—C17	1.252 (3)	C19—C20	1.387 (4)
N1—C1	1.340 (4)	C1—H1	0.9300
N1—C5	1.342 (4)	C2—H2	0.9300
N2—C10	1.326 (5)	C4—H4	0.9300
N2—C11	1.337 (4)	C5—H5	0.9300
N3—C19	1.388 (4)	C6—H6A	0.9700
N3—H3A	0.8600	C6—H6B	0.9700
N3—H3B	0.8600	C7—H7A	0.9700
C1—C2	1.375 (4)	C7—H7B	0.9700
C2—C3	1.386 (4)	C9—H9	0.9300
C3—C6	1.511 (5)	C10—H10	0.9300
C3—C4	1.388 (5)	C11—H11	0.9300
C4—C5	1.370 (4)	C12—H12	0.9300
C6—C7	1.489 (5)	C15—H15	0.9300
C7—C8	1.502 (5)	C18—H18	0.9300
C8—C12	1.373 (5)	C20—H20	0.9300
C8—C9	1.379 (5)

Co1···C15ⁱⁱ	3.893 (3)	C19···C18^ix	3.421 (4)
Co1···H15ⁱⁱ	3.1900	C1···H3A^iv	2.7500
O1···O4ⁱⁱⁱ	3.151 (3)	C2···H3A^iv	2.8000
O1···N1	2.913 (3)	C4···H7A	2.7100
O1···N2ⁱ	3.111 (3)	C6···H6A^vi	3.0900
O1···C5	2.995 (4)	C7···H4	2.8200
O1···C10ⁱ	3.246 (4)	C9···H6A	3.0000
O1···O2ⁱⁱ	3.235 (3)	C11···H15^vi	3.0400
O1···C7^iv	3.362 (5)	C12···H3B^xiii	2.7500
O2···O1ⁱⁱ	3.235 (3)	C13···H10ⁱ	2.7500
O2···C10ⁱ	3.276 (5)	C17···H11^viii	2.7400
O2···O3^v	3.155 (3)	C18···H6B^xii	2.9900
O2···N2^vi	3.001 (4)	C19···H6B^xii	2.9900
O2···C1ⁱⁱ	3.241 (4)	C20···H7B^iv	3.0100
O2···N1ⁱⁱ	2.917 (3)	H1···O2ⁱⁱ	2.8800
O3···N1^vii	2.988 (3)	H2···H6B	2.4000
O3···C1^vii	3.269 (4)	H3A···H20	2.4200
O3···N2^viii	3.060 (3)	H3A···C1^iv	2.7500
O3···C11^viii	3.082 (4)	H3A···C2^iv	2.8000
O3···O2^v	3.155 (3)	H3B···C12^xii	2.7500
O4···C4^ix	3.271 (4)	H3B···H6B^xii	2.3300
O4···O1^vii	3.151 (3)	H3B···H12^xii	2.5400
O4···N2^viii	3.116 (3)	H3B···H18	2.4400
O4···N1^vii	3.099 (3)	H4···C7	2.8200
O1···H5	2.4600	H4···H7A	2.2300
O1···H20	2.5000	H4···O4^ix	2.3500
O1···H10ⁱ	2.7100	H5···O1	2.4600
O1···H7A^iv	2.8300	H5···H20	2.5700
O2···H15	2.5100	H6A···C9	3.0000
O2···H10ⁱ	2.4400	H6A···C6^vi	3.0900
O2···H1ⁱⁱ	2.8800	H6A···H6A^vi	2.3200
O3···H15	2.5900	H6B···N3^xiii	2.6500
O3···H15^v	2.5600	H6B···C18^xiii	2.9900
O3···H11^viii	2.4700	H6B···C19^xiii	2.9900
O3···H11^vi	2.8800	H6B···H2	2.4000
O4···H18	2.6500	H6B···H3B^xiii	2.3300
O4···H4^ix	2.3500	H7A···C4	2.7100
O4···H7A^ix	2.6500	H7A···H4	2.2300
N1···O1	2.913 (3)	H7A···H9	2.5300
N1···O3ⁱⁱⁱ	2.988 (3)	H7A···O1^iv	2.8300
N1···O4ⁱⁱⁱ	3.099 (3)	H7A···O4^ix	2.6500
N1···C17ⁱⁱⁱ	3.312 (4)	H7B···H12	2.4200
N1···O2ⁱⁱ	2.917 (3)	H7B···C20^iv	3.0100
N2···O1^x	3.111 (3)	H7B···H20^iv	2.5000
N2···O3^xi	3.060 (3)	H9···H7A	2.5300
N2···O4^xi	3.116 (3)	H10···O1^x	2.7100
N2···C17^xi	3.282 (4)	H10···O2^x	2.4400
N2···O2^vi	3.001 (4)	H10···C13^x	2.7500
N3···C16^ix	3.405 (4)	H11···O3^xi	2.4700
N3···H6B^xii	2.6500	H11···C17^xi	2.7400
C4···O4^ix	3.271 (4)	H11···O3^vi	2.8800
C7···O1^iv	3.362 (5)	H12···H3B^xiii	2.5400
C10···O2^x	3.276 (5)	H12···H7B	2.4200
C10···C13^x	3.543 (5)	H15···O2	2.5100
C11···C17^xi	3.301 (4)	H15···O3	2.5900
C11···C15^vi	3.524 (4)	H15···Co1ⁱⁱ	3.1900
C11···O3^xi	3.082 (4)	H15···O3^v	2.5600
C13···C10ⁱ	3.543 (5)	H15···C11^vi	3.0400
C15···C11^vi	3.524 (4)	H18···O4	2.6500
C15···Co1ⁱⁱ	3.893 (3)	H18···H3B	2.4400
C16···N3^ix	3.405 (4)	H20···O1	2.5000
C17···C11^viii	3.301 (4)	H20···H3A	2.4200
C17···N2^viii	3.282 (4)	H20···H5	2.5700
C18···C18^ix	3.573 (4)	H20···H7B^iv	2.5000
C18···C19^ix	3.421 (4)

O1—Co1—N1	87.24 (8)	O1—C13—C14	117.0 (3)
O1—Co1—N2ⁱ	95.05 (9)	C13—C14—C15	119.3 (3)
O1—Co1—O3ⁱⁱⁱ	154.55 (8)	C13—C14—C20	120.9 (3)
O1—Co1—O4ⁱⁱⁱ	95.00 (8)	C15—C14—C20	119.7 (3)
O1—Co1—C17ⁱⁱⁱ	124.90 (9)	C14—C15—C16	119.5 (3)
O1—Co1—O2ⁱⁱ	105.91 (8)	C17—C16—C18	120.5 (3)
N1—Co1—N2ⁱ	177.68 (9)	C15—C16—C18	120.6 (3)
O3ⁱⁱⁱ—Co1—N1	87.51 (7)	C15—C16—C17	118.9 (3)
O4ⁱⁱⁱ—Co1—N1	89.38 (8)	O3—C17—O4	121.1 (3)
N1—Co1—C17ⁱⁱⁱ	89.68 (9)	O3—C17—C16	118.6 (3)
O2ⁱⁱ—Co1—N1	88.18 (8)	Co1^vii—C17—O3	58.69 (14)
O3ⁱⁱⁱ—Co1—N2ⁱ	90.27 (9)	O4—C17—C16	120.3 (3)
O4ⁱⁱⁱ—Co1—N2ⁱ	90.08 (9)	Co1^vii—C17—O4	62.59 (15)
N2ⁱ—Co1—C17ⁱⁱⁱ	88.72 (10)	Co1^vii—C17—C16	174.0 (2)
O2ⁱⁱ—Co1—N2ⁱ	91.52 (9)	C16—C18—C19	120.5 (3)
O3ⁱⁱⁱ—Co1—O4ⁱⁱⁱ	60.05 (7)	N3—C19—C18	120.9 (3)
O3ⁱⁱⁱ—Co1—C17ⁱⁱⁱ	30.19 (9)	N3—C19—C20	120.9 (3)
O2ⁱⁱ—Co1—O3ⁱⁱⁱ	98.80 (8)	C18—C19—C20	118.3 (3)
O4ⁱⁱⁱ—Co1—C17ⁱⁱⁱ	29.93 (9)	C14—C20—C19	121.4 (3)
O2ⁱⁱ—Co1—O4ⁱⁱⁱ	158.80 (7)	N1—C1—H1	118.00
O2ⁱⁱ—Co1—C17ⁱⁱⁱ	128.97 (9)	C2—C1—H1	118.00
Co1—O1—C13	130.47 (19)	C1—C2—H2	120.00
Co1ⁱⁱ—O2—C13	148.9 (2)	C3—C2—H2	120.00
Co1^vii—O3—C17	91.12 (17)	C3—C4—H4	120.00
Co1^vii—O4—C17	87.48 (18)	C5—C4—H4	120.00
Co1—N1—C1	123.40 (18)	N1—C5—H5	118.00
Co1—N1—C5	120.13 (18)	C4—C5—H5	118.00
C1—N1—C5	116.3 (2)	C3—C6—H6A	109.00
C10—N2—C11	115.9 (3)	C3—C6—H6B	109.00
Co1^x—N2—C10	121.2 (2)	C7—C6—H6A	109.00
Co1^x—N2—C11	122.7 (2)	C7—C6—H6B	109.00
C19—N3—H3B	120.00	H6A—C6—H6B	108.00
H3A—N3—H3B	120.00	C6—C7—H7A	109.00
C19—N3—H3A	120.00	C6—C7—H7B	109.00
N1—C1—C2	123.5 (3)	C8—C7—H7A	109.00
C1—C2—C3	120.1 (3)	C8—C7—H7B	109.00
C2—C3—C4	116.3 (3)	H7A—C7—H7B	108.00
C2—C3—C6	122.1 (3)	C8—C9—H9	120.00
C4—C3—C6	121.5 (3)	C10—C9—H9	120.00
C3—C4—C5	120.3 (3)	N2—C10—H10	118.00
N1—C5—C4	123.5 (3)	C9—C10—H10	118.00
C3—C6—C7	114.5 (3)	N2—C11—H11	118.00
C6—C7—C8	113.7 (3)	C12—C11—H11	118.00
C9—C8—C12	116.0 (3)	C8—C12—H12	120.00
C7—C8—C12	122.5 (3)	C11—C12—H12	120.00
C7—C8—C9	121.6 (4)	C14—C15—H15	120.00
C8—C9—C10	120.1 (3)	C16—C15—H15	120.00
N2—C10—C9	124.0 (4)	C16—C18—H18	120.00
N2—C11—C12	123.2 (3)	C19—C18—H18	120.00
C8—C12—C11	120.8 (3)	C14—C20—H20	119.00
O2—C13—C14	118.6 (3)	C19—C20—H20	119.00
O1—C13—O2	124.4 (3)

N1—Co1—O1—C13	−97.8 (3)	Co1^x—N2—C10—C9	−177.1 (3)
N2ⁱ—Co1—O1—C13	82.6 (3)	C10—N2—C11—C12	0.9 (5)
O3ⁱⁱⁱ—Co1—O1—C13	−176.1 (2)	Co1^x—N2—C11—C12	177.1 (3)
O4ⁱⁱⁱ—Co1—O1—C13	173.1 (3)	N1—C1—C2—C3	1.0 (5)
C17ⁱⁱⁱ—Co1—O1—C13	174.5 (2)	C1—C2—C3—C4	0.2 (5)
O2ⁱⁱ—Co1—O1—C13	−10.5 (3)	C1—C2—C3—C6	179.9 (3)
O1—Co1—N1—C1	155.5 (2)	C2—C3—C4—C5	−0.9 (5)
O1—Co1—N1—C5	−29.6 (2)	C6—C3—C4—C5	179.4 (3)
O3ⁱⁱⁱ—Co1—N1—C1	−49.4 (2)	C2—C3—C6—C7	133.5 (4)
O3ⁱⁱⁱ—Co1—N1—C5	125.5 (2)	C4—C3—C6—C7	−46.8 (5)
O4ⁱⁱⁱ—Co1—N1—C1	−109.5 (2)	C3—C4—C5—N1	0.6 (5)
O4ⁱⁱⁱ—Co1—N1—C5	65.4 (2)	C3—C6—C7—C8	176.0 (3)
C17ⁱⁱⁱ—Co1—N1—C1	−79.6 (2)	C6—C7—C8—C9	−80.7 (5)
C17ⁱⁱⁱ—Co1—N1—C5	95.4 (2)	C6—C7—C8—C12	98.6 (4)
O2ⁱⁱ—Co1—N1—C1	49.5 (2)	C7—C8—C9—C10	178.5 (3)
O2ⁱⁱ—Co1—N1—C5	−135.6 (2)	C12—C8—C9—C10	−0.9 (5)
O1—Co1—N2ⁱ—C10ⁱ	−26.1 (3)	C7—C8—C12—C11	−178.4 (3)
O1—Co1—N2ⁱ—C11ⁱ	157.9 (2)	C9—C8—C12—C11	1.0 (5)
O1—Co1—O3ⁱⁱⁱ—C17ⁱⁱⁱ	−15.4 (3)	C8—C9—C10—N2	0.9 (6)
N1—Co1—O3ⁱⁱⁱ—C17ⁱⁱⁱ	−93.66 (18)	N2—C11—C12—C8	−1.0 (5)
O1—Co1—O4ⁱⁱⁱ—C17ⁱⁱⁱ	177.63 (18)	O1—C13—C14—C15	−170.9 (3)
N1—Co1—O4ⁱⁱⁱ—C17ⁱⁱⁱ	90.45 (18)	O1—C13—C14—C20	6.7 (4)
O1—Co1—C17ⁱⁱⁱ—O3ⁱⁱⁱ	172.00 (15)	O2—C13—C14—C15	10.6 (4)
O1—Co1—C17ⁱⁱⁱ—O4ⁱⁱⁱ	−2.9 (2)	O2—C13—C14—C20	−171.8 (3)
N1—Co1—C17ⁱⁱⁱ—O3ⁱⁱⁱ	85.58 (17)	C13—C14—C15—C16	178.8 (3)
N1—Co1—C17ⁱⁱⁱ—O4ⁱⁱⁱ	−89.30 (17)	C20—C14—C15—C16	1.2 (5)
O1—Co1—O2ⁱⁱ—C13ⁱⁱ	86.0 (4)	C13—C14—C20—C19	−179.3 (3)
N1—Co1—O2ⁱⁱ—C13ⁱⁱ	172.6 (4)	C15—C14—C20—C19	−1.7 (5)
Co1—O1—C13—O2	−25.5 (5)	C14—C15—C16—C17	−178.6 (3)
Co1—O1—C13—C14	156.1 (2)	C14—C15—C16—C18	1.0 (5)
Co1ⁱⁱ—O2—C13—O1	97.8 (4)	C15—C16—C17—O3	28.8 (4)
Co1ⁱⁱ—O2—C13—C14	−83.8 (4)	C15—C16—C17—O4	−150.4 (3)
Co1^vii—O3—C17—O4	5.3 (3)	C18—C16—C17—O3	−150.7 (3)
Co1^vii—O3—C17—C16	−173.9 (3)	C18—C16—C17—O4	30.1 (5)
Co1^vii—O4—C17—O3	−5.1 (3)	C15—C16—C18—C19	−2.6 (5)
Co1^vii—O4—C17—C16	174.1 (3)	C17—C16—C18—C19	176.9 (3)
Co1—N1—C1—C2	173.8 (2)	C16—C18—C19—N3	−179.2 (3)
C5—N1—C1—C2	−1.3 (4)	C16—C18—C19—C20	2.1 (5)
Co1—N1—C5—C4	−174.8 (2)	N3—C19—C20—C14	−178.7 (3)
C1—N1—C5—C4	0.5 (4)	C18—C19—C20—C14	0.1 (5)
C11—N2—C10—C9	−0.8 (5)

Symmetry codes: (i) x−1, y, z+1; (ii) −x, −y+1, −z+1; (iii) x, y−1, z; (iv) −x, −y+1, −z; (v) −x, −y+2, −z+1; (vi) −x+1, −y+1, −z; (vii) x, y+1, z; (viii) x−1, y+1, z+1; (ix) −x, −y+2, −z; (x) x+1, y, z−1; (xi) x+1, y−1, z−1; (xii) x−1, y+1, z; (xiii) x+1, y−1, z.

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the N1-pyridine ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O4^ix	0.93	2.35	3.271 (4)	173
C5—H5···O1	0.93	2.46	2.995 (4)	117
C10—H10···O2^x	0.93	2.44	3.276 (5)	150
C11—H11···O3^xi	0.93	2.47	3.082 (4)	124
C15—H15···O3^v	0.93	2.56	3.487 (4)	175
N3—H3A···Cg4^iv	0.86	2.92	3.765 (3)	169
C11—H11···Cg3^xi	0.93	2.65	3.019 (3)	105

Symmetry codes: (iv) −x, −y+1, −z; (v) −x, −y+2, −z+1; (ix) −x, −y+2, −z; (x) x+1, y, z−1; (xi) x+1, y−1, z−1.

Experimental details

Crystal data
Chemical formula	[Co(C₈H₅NO₄)(C₁₂H₁₂N₂)]
M_r	422.30
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.9093 (2), 10.0755 (2), 10.5065 (3)
α, β, γ (°)	78.301 (1), 83.560 (1), 68.074 (2)
V (Å³)	952.12 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.93
Crystal size (mm)	0.22 × 0.18 × 0.08

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	Multi-scan (SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.732, 0.840
No. of measured, independent and observed [I > 2σ(I)] reflections	7715, 3356, 3003
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.120, 1.16
No. of reflections	3356
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.60

Computer programs: COLLECT (Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Selected bond lengths (Å) top

Co1—N1	2.178 (2)	Co1—O2ⁱⁱ	2.011 (2)
Co1—N2ⁱ	2.175 (3)	Co1—O3ⁱⁱⁱ	2.1426 (19)
Co1—O1	2.0416 (18)	Co1—O4ⁱⁱⁱ	2.228 (2)

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

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the N1-pyridine ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O4^iv	0.93	2.35	3.271 (4)	173
C10—H10···O2^v	0.93	2.44	3.276 (5)	150
C15—H15···O3^vi	0.93	2.56	3.487 (4)	175
N3—H3A···Cg4^vii	0.86	2.92	3.765 (3)	169

Symmetry codes: (iv) −x, −y+2, −z; (v) x+1, y, z−1; (vi) −x, −y+2, −z+1; (vii) −x, −y+1, −z.

Acknowledgements

This work was supported financially by Yuanpei University, Taiwan.

References

He, H.-Y., Zhou, Y.-L. & Zhu, L.-G. (2006). Chin. J. Inorg. Chem. 22, 142–144. CAS Google Scholar
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter & R. M. Sweet, pp. 307–326. London: Academic Press. Google Scholar
Ou, Y.-J., Ma, C.-B., Chen, H., Wang, H.-S., Chen, C.-N. & Liu, Q.-T. (2008). Chin. J. Struct. Chem. 27, 159–162. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tang, E., Dai, Y.-M., Li, Z.-J., Wang, X.-Q., Yin, P.-X. & Yao, Y.-G. (2007). Chin. J. Struct. Chem. 26, 529–532. CAS Google Scholar
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Volume 66| Part 9| September 2010| Pages m1069-m1070

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