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

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)meth-yl]oxalamide (BPMO) ligands and four O atoms from two centrosymmetric oxalate anions in a distorted octa-hedral 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.

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 CoII complexes, see: Ma et al. (2005 ▶).

Experimental

Crystal data

[Co(C2O4)(C14H14N4O2)]

M = 417.24

Monoclinic,

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

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

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.149

S = 0.98

4254 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.39 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814015608/bt6986sup1.cif

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

Click here for additional data file.

x y z x y z x y z x y z . DOI: 10.1107/S1600536814015608/bt6986fig1.tif

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 + , z + ; (iv) x + 1, − y + , z − .

Click here for additional data file.

. DOI: 10.1107/S1600536814015608/bt6986fig2.tif

View of the three-dimensional structure of (I).

CCDC reference: 1012047

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Co(C2O4)(C14H14N4O2)]	F(000) = 852
Mr = 417.24	Dx = 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

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

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(Fo2) + (0.0591P)2] where P = (Fo2 + 2Fc2)/3
4254 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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—N4iv	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—N4iv	92.74 (13)
H11A—C11—H11B	107.6	O3—Co1—N4iv	92.70 (13)
C13—C12—C16	117.9 (4)	N1—Co1—N4iv	94.43 (15)
C13—C12—C11	125.3 (4)	O2ii—Co1—N4iv	91.71 (14)
C16—C12—C11	116.8 (4)	O4i—Co1—N4iv	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—N4iv	−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—N4iv	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—N4iv	124.2 (4)
C14—C15—N4—C16	−1.2 (9)	C3—N1—Co1—N4iv	−58.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O6v	0.86	2.14	2.863 (5)	142

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) .