Crystal structure of poly[{μ-N,N′-bis[(pyridin-4-yl)meth­yl]oxalamide}-μ-oxalato-cobalt(II)]

Zou, H.; Qi, Y.

doi:10.1107/S1600536814015608

metal-organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages m307-m308

doi:10.1107/S1600536814015608

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Crystal structure of poly[{μ-N,N′-bis[(pyridin-4-yl)methyl]oxalamide}-μ-oxalato-cobalt(II)]

Hengye Zou ^a and Yanjuan Qi ^a ^*

^aDepartment of Chemistry, Changchun Normal University, Changchun 130032, People's Republic of China
^*Correspondence e-mail: qiyjchem@163.com

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 26 June 2014; accepted 3 July 2014; online 1 August 2014)

In the polymeric title compound, [Co(C₂O₄)(C₁₄H₁₄N₄O₂)]_n, the Co^II atom is six-coordinated by two N atoms from symmetry-related bis[(pyridin-4-yl)methyl]oxalamide (BPMO) ligands and four O atoms from two centrosymmetric oxalate anions in a distorted octahedral coordination geometry. The Co^II atoms are linked by the oxalate anions into a chain running parallel to [100]. The chains are linked by the BPMO ligands into a three-dimensional architecture. In addition, N—H⋯O hydrogen bonds stabilize the crystal packing.

Keywords: crystal structure; metal-organic framework; cobalt(II); oxalate anion; hydrogen bonds.

CCDC reference: 1012047

1. Related literature

For information on compounds with metal-organic framework structures, see: Kitagawa et al. (2004 ); Ma et al. (2009 ); Li et al. (2005 ); Wang et al. (2007 ). For related Co^II complexes, see: Ma et al. (2005 ).

2. Experimental

2.1. Crystal data

[Co(C₂O₄)(C₁₄H₁₄N₄O₂)]
M_r = 417.24
Monoclinic, P 2₁ /c
a = 8.4143 (12) Å
b = 24.421 (4) Å
c = 9.2884 (14) Å
β = 113.322 (2)°
V = 1752.7 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.02 mm⁻¹
T = 293 K
0.43 × 0.25 × 0.25 mm

2.2. Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.740, T_max = 0.785
11121 measured reflections
4254 independent reflections
2027 reflections with I > 2σ(I)
R_int = 0.085

2.3. Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.149
S = 0.98
4254 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O6ⁱ	0.86	2.14	2.863 (5)	142
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1012047

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814015608/bt6986sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814015608/bt6986Isup2.hkl

checkCIF report

Comment top

Design of effective ligands and the proper choice of metal centers are the keys to design and construct novel metal-organic frameworks (Kitagawa et al., 2004; Ma et al., 2009). These complexes can be specially designed by the careful selection of metal cations with preferred coordination geometries, the nature of the anions, the structure of the connecting ligands, and the reaction conditions (Li et al., 2005; Wang et al., 2007). We selected oxalic acid as an organic carboxylate anion and N,N'-Bis-pyridin-4-ylmethyl-oxalamide (BPMO) as a N-donor neutral ligand, generating a coordination compound, [Co(C₂O₄)(BPMO)]_n, which is reported here.

In the asymmetric unit of the title compound, [Co(C₂O₄)(BPMO)]_n, the central Co^II is six-coordinated by two nitrogen atoms from different BPMO ligands and four oxygen atoms from two oxalate anions in a distorted octahedral coordination geometry. The Co—N and Co—O distances are comparable to those found in other crystallographically characterized Co^II complexes (Ma et al., 2005). The Co^II atoms are linked by the oxalate anions to give a one-dimensional chain. The chains are linked by BPMO ligands and extend the chains into a three-dimensional supramolecular architecture. Moreover, the hydrogen bonds between the N-donor neutral ligand and oxalate, are crucial for stabilizing the three-dimensional framework.

Related literature top

For information on compounds with metal-organic framework structures, see: Kitagawa et al. (2004); Ma et al. (2009); Li et al. (2005); Wang et al. (2007). For related Co^II complexes, see: Ma et al. (2005).

Experimental top

The synthesis was performed under hydrothermal conditions. A mixture of Co(CH₃COO)₂^.4(H₂O),(0.2 mmol, 0.05 g), N,N'-Bis-pyridin-4-ylmethyl-oxalamide (0.2 mmol, 0.054 g), sodium oxalate (0.2 mmol,0.026 g) and H₂O(15 ml) in a 25 ml stainless steel reactor with a Teflon liner was heated from 293 to 443 K in 2 h and a constant temperature was maintained at 443 K for 72 h, after which the mixture was cooled to 298 K. Pink crystals of (I) were recovered from the reaction.

Computing details top

Data collection: APEX2 (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. A view of the molecule of (I). Displacement ellipsoids are drawn at the 30% probability level. (i) - x + 1, -y, - z + 1; (ii) -x, -y, - z + 1; (iii) x, - y + 1/2, z + 1/2; (iv) x + 1, - y + 1/2, z - 1/2.
	Fig. 2. View of the three-dimensional structure of (I).

Poly[{µ-N,N'-bis[(pyridin-4-yl)methyl]oxalamide}-µ-oxalato-cobalt(II)] top

Crystal data top

[Co(C₂O₄)(C₁₄H₁₄N₄O₂)]	F(000) = 852
M_r = 417.24	D_x = 1.581 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4380 reflections
a = 8.4143 (12) Å	θ = 1.7–22.8°
b = 24.421 (4) Å	µ = 1.02 mm⁻¹
c = 9.2884 (14) Å	T = 293 K
β = 113.322 (2)°	Block, pink
V = 1752.7 (4) Å³	0.43 × 0.25 × 0.25 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	4254 independent reflections
Radiation source: fine-focus sealed tube	2027 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.085
phi and ω scans	θ_max = 28.4°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→10
T_min = 0.740, T_max = 0.785	k = −32→32
11121 measured reflections	l = −12→10

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.149	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0591P)²] where P = (F_o² + 2F_c²)/3
4254 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

[Co(C₂O₄)(C₁₄H₁₄N₄O₂)]	V = 1752.7 (4) Å³
M_r = 417.24	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.4143 (12) Å	µ = 1.02 mm⁻¹
b = 24.421 (4) Å	T = 293 K
c = 9.2884 (14) Å	0.43 × 0.25 × 0.25 mm
β = 113.322 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	4254 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2027 reflections with I > 2σ(I)
T_min = 0.740, T_max = 0.785	R_int = 0.085
11121 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 0.98	Δρ_max = 0.49 e Å⁻³
4254 reflections	Δρ_min = −0.39 e Å⁻³
244 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
C1	0.5475 (6)	0.02677 (18)	0.5426 (6)	0.0391 (12)
C2	−0.0727 (6)	0.00051 (18)	0.4182 (6)	0.0373 (11)
C3	0.0325 (7)	0.0938 (2)	0.0435 (7)	0.0588 (15)
H3A	−0.0628	0.0983	0.0692	0.071*
C4	0.0141 (7)	0.1061 (2)	−0.1055 (7)	0.0644 (16)
H4	−0.0906	0.1187	−0.1797	0.077*
C5	0.1578 (7)	0.0990 (2)	−0.1424 (6)	0.0553 (15)
H5	0.1507	0.1079	−0.2422	0.066*
C6	0.3094 (6)	0.07904 (17)	−0.0329 (6)	0.0358 (11)
C7	0.3141 (6)	0.06856 (18)	0.1129 (6)	0.0413 (12)
H7	0.4172	0.0555	0.1884	0.050*
C8	0.4646 (6)	0.06836 (16)	−0.0724 (6)	0.0398 (12)
H8A	0.5578	0.0537	0.0195	0.048*
H8B	0.4343	0.0409	−0.1543	0.048*
C9	0.5876 (6)	0.15839 (19)	−0.0278 (6)	0.0372 (11)
C10	0.6436 (5)	0.20856 (18)	−0.0958 (6)	0.0353 (11)
C11	0.7359 (6)	0.30333 (18)	−0.0376 (6)	0.0411 (12)
H11A	0.7224	0.3306	0.0328	0.049*
H11B	0.6576	0.3130	−0.1432	0.049*
C12	0.9189 (6)	0.30606 (19)	−0.0279 (5)	0.0396 (12)
C13	1.0379 (7)	0.2660 (2)	0.0275 (7)	0.0700 (18)
H13	1.0094	0.2334	0.0632	0.084*
C14	1.2033 (7)	0.2734 (2)	0.0312 (8)	0.083 (2)
H14	1.2859	0.2458	0.0666	0.100*
C15	1.2411 (7)	0.3229 (2)	−0.0193 (7)	0.0631 (16)
H15	1.3517	0.3281	−0.0165	0.076*
C16	0.9683 (6)	0.35427 (19)	−0.0767 (6)	0.0431 (12)
H16	0.8861	0.3819	−0.1153	0.052*
N1	0.1806 (5)	0.07571 (16)	0.1551 (5)	0.0455 (11)
N2	0.5257 (5)	0.11716 (15)	−0.1243 (4)	0.0403 (10)
H2	0.5213	0.1190	−0.2183	0.048*
N3	0.6855 (4)	0.25082 (15)	0.0010 (4)	0.0423 (10)
H3	0.6826	0.2467	0.0918	0.051*
N4	1.1276 (5)	0.36374 (16)	−0.0717 (5)	0.0439 (10)
O1	−0.0491 (4)	0.02611 (12)	0.3106 (4)	0.0434 (8)
O2	−0.2077 (4)	−0.02540 (13)	0.4033 (4)	0.0503 (9)
O3	0.4618 (4)	0.07115 (12)	0.5055 (4)	0.0446 (9)
O4	0.6991 (4)	0.02217 (12)	0.6401 (4)	0.0494 (9)
O5	0.5999 (5)	0.15868 (13)	0.1070 (4)	0.0612 (11)
O6	0.6455 (4)	0.20801 (12)	−0.2267 (4)	0.0464 (8)
Co1	0.20072 (8)	0.05586 (2)	0.38091 (8)	0.0405 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.035 (3)	0.043 (3)	0.049 (3)	0.003 (2)	0.026 (3)	−0.001 (2)
C2	0.034 (3)	0.033 (2)	0.051 (3)	0.002 (2)	0.023 (2)	−0.008 (2)
C3	0.050 (4)	0.067 (4)	0.068 (4)	0.013 (3)	0.034 (3)	0.009 (3)
C4	0.043 (4)	0.087 (4)	0.053 (4)	0.018 (3)	0.009 (3)	0.015 (3)
C5	0.063 (4)	0.061 (4)	0.044 (4)	0.003 (3)	0.023 (3)	0.001 (3)
C6	0.037 (3)	0.026 (2)	0.043 (3)	−0.004 (2)	0.015 (3)	−0.005 (2)
C7	0.034 (3)	0.044 (3)	0.046 (3)	0.006 (2)	0.016 (2)	0.004 (3)
C8	0.053 (3)	0.027 (2)	0.048 (3)	−0.004 (2)	0.029 (3)	−0.001 (2)
C9	0.035 (3)	0.041 (3)	0.037 (3)	−0.010 (2)	0.016 (2)	−0.002 (2)
C10	0.034 (3)	0.039 (3)	0.038 (3)	−0.010 (2)	0.019 (2)	−0.001 (2)
C11	0.048 (3)	0.040 (3)	0.044 (3)	−0.010 (2)	0.027 (3)	0.001 (2)
C12	0.043 (3)	0.042 (3)	0.034 (3)	−0.013 (2)	0.016 (2)	−0.001 (2)
C13	0.052 (4)	0.045 (3)	0.109 (6)	−0.009 (3)	0.028 (4)	0.015 (3)
C14	0.050 (4)	0.046 (4)	0.142 (7)	0.003 (3)	0.026 (4)	0.016 (4)
C15	0.045 (3)	0.048 (3)	0.104 (5)	−0.003 (3)	0.036 (3)	−0.003 (3)
C16	0.039 (3)	0.045 (3)	0.052 (3)	−0.006 (2)	0.024 (3)	0.001 (3)
N1	0.041 (3)	0.047 (2)	0.054 (3)	0.0103 (19)	0.024 (2)	0.009 (2)
N2	0.052 (3)	0.041 (2)	0.035 (2)	−0.0080 (19)	0.026 (2)	−0.0039 (19)
N3	0.052 (3)	0.045 (2)	0.038 (3)	−0.0204 (19)	0.026 (2)	−0.005 (2)
N4	0.039 (2)	0.042 (2)	0.058 (3)	−0.0088 (19)	0.027 (2)	−0.005 (2)
O1	0.040 (2)	0.044 (2)	0.048 (2)	0.0012 (15)	0.0202 (17)	0.0061 (17)
O2	0.042 (2)	0.057 (2)	0.055 (2)	−0.0090 (17)	0.0222 (18)	−0.0050 (18)
O3	0.0356 (19)	0.0339 (18)	0.070 (3)	0.0063 (14)	0.0269 (18)	0.0041 (16)
O4	0.037 (2)	0.041 (2)	0.065 (3)	0.0040 (16)	0.0145 (19)	−0.0052 (17)
O5	0.098 (3)	0.050 (2)	0.044 (2)	−0.036 (2)	0.037 (2)	−0.0086 (18)
O6	0.064 (2)	0.044 (2)	0.041 (2)	−0.0107 (16)	0.0318 (19)	−0.0026 (16)
Co1	0.0349 (4)	0.0385 (4)	0.0551 (5)	0.0057 (3)	0.0253 (3)	0.0030 (3)

Geometric parameters (Å, º) top

C1—O4	1.243 (5)	C11—N3	1.440 (5)
C1—O3	1.271 (5)	C11—C12	1.508 (6)
C1—C1ⁱ	1.573 (9)	C11—H11A	0.9700
C2—O2	1.259 (5)	C11—H11B	0.9700
C2—O1	1.260 (5)	C12—C13	1.348 (6)
C2—C2ⁱⁱ	1.527 (9)	C12—C16	1.383 (6)
C3—N1	1.342 (6)	C13—C14	1.390 (7)
C3—C4	1.363 (7)	C13—H13	0.9300
C3—H3A	0.9300	C14—C15	1.380 (7)
C4—C5	1.392 (7)	C14—H14	0.9300
C4—H4	0.9300	C15—N4	1.332 (6)
C5—C6	1.369 (6)	C15—H15	0.9300
C5—H5	0.9300	C16—N4	1.343 (5)
C6—C7	1.364 (6)	C16—H16	0.9300
C6—C8	1.512 (6)	N1—Co1	2.093 (4)
C7—N1	1.339 (5)	N2—H2	0.8600
C7—H7	0.9300	N3—H3	0.8600
C8—N2	1.454 (5)	N4—Co1ⁱⁱⁱ	2.155 (4)
C8—H8A	0.9700	O1—Co1	2.070 (3)
C8—H8B	0.9700	O2—Co1ⁱⁱ	2.117 (3)
C9—O5	1.215 (5)	O3—Co1	2.072 (3)
C9—N2	1.311 (5)	O4—Co1ⁱ	2.124 (3)
C9—C10	1.535 (6)	Co1—O2ⁱⁱ	2.117 (3)
C10—O6	1.222 (5)	Co1—O4ⁱ	2.124 (3)
C10—N3	1.322 (5)	Co1—N4^iv	2.155 (4)

O4—C1—O3	125.7 (4)	C12—C13—H13	120.0
O4—C1—C1ⁱ	117.5 (5)	C14—C13—H13	120.0
O3—C1—C1ⁱ	116.8 (6)	C15—C14—C13	117.9 (5)
O2—C2—O1	125.5 (4)	C15—C14—H14	121.0
O2—C2—C2ⁱⁱ	115.7 (6)	C13—C14—H14	121.0
O1—C2—C2ⁱⁱ	118.8 (5)	N4—C15—C14	123.5 (5)
N1—C3—C4	123.7 (5)	N4—C15—H15	118.2
N1—C3—H3A	118.2	C14—C15—H15	118.2
C4—C3—H3A	118.2	N4—C16—C12	124.1 (4)
C3—C4—C5	117.5 (5)	N4—C16—H16	117.9
C3—C4—H4	121.2	C12—C16—H16	117.9
C5—C4—H4	121.2	C7—N1—C3	116.5 (5)
C6—C5—C4	120.4 (5)	C7—N1—Co1	121.2 (3)
C6—C5—H5	119.8	C3—N1—Co1	122.2 (3)
C4—C5—H5	119.8	C9—N2—C8	120.0 (4)
C7—C6—C5	117.2 (4)	C9—N2—H2	120.0
C7—C6—C8	121.4 (4)	C8—N2—H2	120.0
C5—C6—C8	121.5 (4)	C10—N3—C11	123.5 (4)
N1—C7—C6	124.7 (5)	C10—N3—H3	118.3
N1—C7—H7	117.7	C11—N3—H3	118.3
C6—C7—H7	117.7	C15—N4—C16	116.4 (4)
N2—C8—C6	113.1 (3)	C15—N4—Co1ⁱⁱⁱ	122.3 (3)
N2—C8—H8A	109.0	C16—N4—Co1ⁱⁱⁱ	120.8 (3)
C6—C8—H8A	109.0	C2—O1—Co1	112.5 (3)
N2—C8—H8B	109.0	C2—O2—Co1ⁱⁱ	112.7 (3)
C6—C8—H8B	109.0	C1—O3—Co1	111.1 (3)
H8A—C8—H8B	107.8	C1—O4—Co1ⁱ	110.2 (3)
O5—C9—N2	123.9 (4)	O1—Co1—O3	163.58 (13)
O5—C9—C10	120.3 (4)	O1—Co1—N1	95.51 (15)
N2—C9—C10	115.8 (4)	O3—Co1—N1	99.50 (14)
O6—C10—N3	125.5 (4)	O1—Co1—O2ⁱⁱ	79.59 (13)
O6—C10—C9	121.8 (4)	O3—Co1—O2ⁱⁱ	84.77 (12)
N3—C10—C9	112.7 (4)	N1—Co1—O2ⁱⁱ	172.33 (14)
N3—C11—C12	114.8 (4)	O1—Co1—O4ⁱ	92.68 (12)
N3—C11—H11A	108.6	O3—Co1—O4ⁱ	80.86 (12)
C12—C11—H11A	108.6	N1—Co1—O4ⁱ	89.62 (14)
N3—C11—H11B	108.6	O2ⁱⁱ—Co1—O4ⁱ	84.76 (13)
C12—C11—H11B	108.6	O1—Co1—N4^iv	92.74 (13)
H11A—C11—H11B	107.6	O3—Co1—N4^iv	92.70 (13)
C13—C12—C16	117.9 (4)	N1—Co1—N4^iv	94.43 (15)
C13—C12—C11	125.3 (4)	O2ⁱⁱ—Co1—N4^iv	91.71 (14)
C16—C12—C11	116.8 (4)	O4ⁱ—Co1—N4^iv	172.90 (15)
C12—C13—C14	120.0 (5)

N1—C3—C4—C5	0.2 (9)	C14—C15—N4—Co1ⁱⁱⁱ	171.3 (5)
C3—C4—C5—C6	1.7 (8)	C12—C16—N4—C15	1.5 (8)
C4—C5—C6—C7	−2.3 (7)	C12—C16—N4—Co1ⁱⁱⁱ	−171.1 (4)
C4—C5—C6—C8	177.0 (5)	O2—C2—O1—Co1	−173.9 (3)
C5—C6—C7—N1	1.0 (7)	C2ⁱⁱ—C2—O1—Co1	5.5 (6)
C8—C6—C7—N1	−178.3 (4)	O1—C2—O2—Co1ⁱⁱ	−174.5 (3)
C7—C6—C8—N2	−121.0 (5)	C2ⁱⁱ—C2—O2—Co1ⁱⁱ	6.2 (6)
C5—C6—C8—N2	59.8 (6)	O4—C1—O3—Co1	−166.2 (4)
O5—C9—C10—O6	174.2 (4)	C1ⁱ—C1—O3—Co1	13.8 (6)
N2—C9—C10—O6	−6.6 (6)	O3—C1—O4—Co1ⁱ	−166.7 (4)
O5—C9—C10—N3	−6.6 (6)	C1ⁱ—C1—O4—Co1ⁱ	13.4 (6)
N2—C9—C10—N3	172.6 (4)	C2—O1—Co1—O3	11.5 (6)
N3—C11—C12—C13	−6.9 (7)	C2—O1—Co1—N1	167.5 (3)
N3—C11—C12—C16	174.7 (4)	C2—O1—Co1—O2ⁱⁱ	−6.5 (3)
C16—C12—C13—C14	−1.3 (9)	C2—O1—Co1—O4ⁱ	77.7 (3)
C11—C12—C13—C14	−179.7 (5)	C2—O1—Co1—N4^iv	−97.7 (3)
C12—C13—C14—C15	1.6 (10)	C1—O3—Co1—O1	51.8 (6)
C13—C14—C15—N4	−0.3 (10)	C1—O3—Co1—N1	−104.0 (3)
C13—C12—C16—N4	−0.3 (8)	C1—O3—Co1—O2ⁱⁱ	69.6 (3)
C11—C12—C16—N4	178.2 (4)	C1—O3—Co1—O4ⁱ	−15.9 (3)
C6—C7—N1—C3	0.9 (7)	C1—O3—Co1—N4^iv	161.1 (3)
C6—C7—N1—Co1	178.1 (3)	C7—N1—Co1—O1	−142.6 (3)
C4—C3—N1—C7	−1.5 (8)	C3—N1—Co1—O1	34.4 (4)
C4—C3—N1—Co1	−178.7 (4)	C7—N1—Co1—O3	30.7 (4)
O5—C9—N2—C8	0.8 (7)	C3—N1—Co1—O3	−152.3 (4)
C10—C9—N2—C8	−178.3 (4)	C7—N1—Co1—O2ⁱⁱ	−92.7 (11)
C6—C8—N2—C9	64.2 (6)	C3—N1—Co1—O2ⁱⁱ	84.3 (11)
O6—C10—N3—C11	1.6 (7)	C7—N1—Co1—O4ⁱ	−50.0 (4)
C9—C10—N3—C11	−177.5 (4)	C3—N1—Co1—O4ⁱ	127.0 (4)
C12—C11—N3—C10	−77.4 (6)	C7—N1—Co1—N4^iv	124.2 (4)
C14—C15—N4—C16	−1.2 (9)	C3—N1—Co1—N4^iv	−58.8 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O6^v	0.86	2.14	2.863 (5)	142

Symmetry code: (v) x, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O6ⁱ	0.86	2.14	2.863 (5)	141.6

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

We thank the Science Foundation of Jilin Province (No. 20140101121JC).

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Volume 70| Part 9| September 2014| Pages m307-m308

doi:10.1107/S1600536814015608

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of poly[{μ-N,N′-bis­[(pyridin-4-yl)meth­yl]oxalamide}-μ-oxalato-cobalt(II)]

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Crystal structure of poly[{μ-N,N′-bis[(pyridin-4-yl)methyl]oxalamide}-μ-oxalato-cobalt(II)]