Poly[(μ3-pyridine-4-carboxyl­ato-κ3O:O′:N)(pyridin-1-ium-4-carboxyl­ato-κO)(thio­cyanato-κN)cobalt(II)]

Neumann, T.; Werner, J.; Jess, I.; Näther, C.

doi:10.1107/S1600536812044431

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page m1435

doi:10.1107/S1600536812044431

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Poly[(μ₃-pyridine-4-carboxylato-κ³O:O′:N)(pyridin-1-ium-4-carboxylato-κO)(thiocyanato-κN)cobalt(II)]

Tristan Neumann,^a Julia Werner,^a Inke Jess ^a and Christian Näther ^a ^*

^aInstitut für Anorganische Chemie, Christian-Albrechts-Universität Kiel, Max-Eyth-Strasse 2, 24118 Kiel, Germany
^*Correspondence e-mail: cnaether@ac.uni-kiel.de

(Received 12 September 2012; accepted 26 October 2012; online 3 November 2012)

In the title compound, [Co(C₆H₅NO₂)(NCS)(C₆H₄NO₂)]_n, the Co²⁺ cation is coordinated by one N and two O atoms of three bridging pyridine-4-carboxylate anions, one O atom of one zwitterionic pyridinium-4-carboxylate ligand and one terminal N-bonding thiocyanate anion within a distorted N₂O₃ trigonal bipyramid. The bridging coordination mode of the ligands leads to the formation of layers parallel to (-101). N—H⋯O hydrogen-bonding interactions within the layers and S⋯S contacts of 3.257 (3) Å between the layers lead to the cohesion of the structure.

Related literature

For general background information on the synthesis and properties of transition metal–thiocyanate coordination polymers, see: Boeckmann & Näther (2010 , 2011 ); Wöhlert et al. (2011 ).

Experimental

Crystal data

[Co(C₆H₅NO₂)(NCS)(C₆H₄NO₂)]
M_r = 362.22
Monoclinic, P 2₁ /n
a = 8.7857 (7) Å
b = 13.5401 (8) Å
c = 12.2054 (9) Å
β = 95.740 (6)°
V = 1444.67 (18) Å³
Z = 4
Mo Kα radiation
μ = 1.35 mm⁻¹
T = 293 K
0.18 × 0.13 × 0.04 mm

Data collection

Stoe IPDS-2 diffractometer
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008 ) T_min = 0.808, T_max = 0.954
12489 measured reflections
2844 independent reflections
2353 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.098
S = 1.13
2844 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—O22	2.004 (2)
Co1—O21ⁱ	2.004 (2)
Co1—N1	2.010 (4)
Co1—O12	2.097 (2)
Co1—N21ⁱⁱ	2.146 (2)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N11—H1N⋯O11ⁱⁱⁱ	0.86	1.80	2.561 (4)	147
Symmetry code: (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2008); cell refinement: X-AREA; data reduction: X-AREA; 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, 2011 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812044431/wm2684sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812044431/wm2684Isup2.hkl

checkCIF report

Comment top

The title compound was prepared within a project on the synthesis and properties of transition metal thiocyanato coordination polymers (Boeckmann & Näther, 2010, 2011; Wöhlert et al., 2011). During our attempts to prepare a one-dimensional coordination polymer based on pyridine-4-carboxylic acid as a co-ligand, crystals of the title compound, [Co(NCS)(C₆H₄NO₂)(C₆H₅NO₂)], (I), were obtained serendipitously and characterized by single crystal X-ray diffraction.

In the crystal structure of (I), the cobalt(II) cation is coordinated by one terminally O-bonded pyridinium-4-carboxylate ligand, one terminally N-bonded thiocyanate anion, one N-bonded µ-1,3,6-bridging pyridine-4-carboxylate and two O-bonded µ-1,3,6-bridging pyridine-4-carboxylate anions (Fig. 1). The coordination polyhedron of the Co²⁺ cations can be described as a distorted trigonal bipyramid (Fig. 1, Table 1).

The Co²⁺ cations are µ-1,3 bridged via pyridine-4-carboxylato anions into dimers, which are further connected into layers parallel to (101) (Fig. 2). The Co···Co distance within the dimer amounts to 3.4951 (6) Å. Within the layers N—H···O hydrogen bonding between the bridging pyridine-4-carboxylate anions and the non-bridging pyridinium carboxylate ligands (Fig. 3 and Table 2) is present. A short S···S contact of 3.257 (3) Å between the layers is also observed.

Related literature top

For general background information on the synthesis and properties of transition metal–thiocyanate coordination polymers, see: Boeckmann & Näther (2010, 2011); Wöhlert et al. (2011).

Experimental top

Cobalt thiocyanate and pyridine-4-carboxylic acid were purchased from Alfa Aesar. The title compound was prepared by the reaction of 43.8 mg Co(NCS)₂ (0.25 mmol), and 61.6 mg pyridine-4-carboxylic acid (0.50 mmol) in 1.5 mL ethanol at 354 K in a closed 10 ml glas culture tube. After several days pink block-shaped crystals of the title compound were obtained.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2008); cell refinement: X-AREA (Stoe & Cie, 2008); data reduction: X-AREA (Stoe & Cie, 2008); 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, 2011); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. : The coordination environment of the Co²⁺ cation in the title compound with labelling and displacement ellipsoids drawn at the 50% probability level. [Symmetry codes: i = -x+1,-y+1,-z+1, ii = -x+1/2, y+1/2, -z+1/2.]
	Fig. 2. : The layers parallel to (101) in the title compound in a projection along the a axis. For clarity, the non-bridging ligands and the thiocyanato anions are not shown.
	Fig. 3. : The N—H···O hydrogen bonding interactions (dashed lines) within the layers in the crystal structure of the title compound.

Poly[(µ₃-pyridine-4-carboxylato-κ³O:O':N)(pyridin- 1-ium-4-carboxylato-κO)(thiocyanato-κN)cobalt(II)] top

Crystal data top

[Co(C₆H₅NO₂)(NCS)(C₆H₄NO₂)]	F(000) = 732
M_r = 362.22	D_x = 1.665 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 12489 reflections
a = 8.7857 (7) Å	θ = 2.3–26.0°
b = 13.5401 (8) Å	µ = 1.35 mm⁻¹
c = 12.2054 (9) Å	T = 293 K
β = 95.740 (6)°	Block, pink
V = 1444.67 (18) Å³	0.18 × 0.13 × 0.04 mm
Z = 4

Data collection top

Stoe IPDS-2 diffractometer	2844 independent reflections
Radiation source: fine-focus sealed tube	2353 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ω scans	θ_max = 26.0°, θ_min = 2.3°
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008)	h = −9→10
T_min = 0.808, T_max = 0.954	k = −16→16
12489 measured reflections	l = −15→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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0434P)² + 0.689P] where P = (F_o² + 2F_c²)/3
2844 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

[Co(C₆H₅NO₂)(NCS)(C₆H₄NO₂)]	V = 1444.67 (18) Å³
M_r = 362.22	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.7857 (7) Å	µ = 1.35 mm⁻¹
b = 13.5401 (8) Å	T = 293 K
c = 12.2054 (9) Å	0.18 × 0.13 × 0.04 mm
β = 95.740 (6)°

Data collection top

Stoe IPDS-2 diffractometer	2844 independent reflections
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008)	2353 reflections with I > 2σ(I)
T_min = 0.808, T_max = 0.954	R_int = 0.041
12489 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.13	Δρ_max = 0.46 e Å⁻³
2844 reflections	Δρ_min = −0.39 e Å⁻³
199 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.55767 (5)	0.54579 (3)	0.37683 (3)	0.04212 (15)
N1	0.6768 (4)	0.5335 (2)	0.2453 (3)	0.0650 (8)
C1	0.7529 (4)	0.5189 (3)	0.1751 (3)	0.0569 (9)
S1	0.85857 (16)	0.50015 (10)	0.07668 (11)	0.0870 (4)
O11	0.7180 (4)	0.3217 (2)	0.3482 (2)	0.0961 (12)
N11	1.0561 (4)	0.2118 (2)	0.6656 (2)	0.0602 (8)
H1N	1.1155	0.1797	0.7133	0.072*
C11	1.0285 (5)	0.3058 (3)	0.6833 (3)	0.0691 (11)
H11	1.0737	0.3363	0.7467	0.083*
O12	0.7060 (4)	0.44642 (18)	0.4654 (2)	0.0746 (9)
C12	0.9336 (5)	0.3592 (3)	0.6092 (3)	0.0626 (10)
H12	0.9141	0.4255	0.6219	0.075*
C13	0.8682 (4)	0.3134 (2)	0.5164 (3)	0.0472 (8)
C14	0.9021 (6)	0.2159 (3)	0.4995 (3)	0.0731 (13)
H14	0.8619	0.1840	0.4356	0.088*
C15	0.9951 (6)	0.1659 (3)	0.5768 (3)	0.0797 (14)
H15	1.0155	0.0993	0.5667	0.096*
C16	0.7540 (5)	0.3656 (3)	0.4352 (3)	0.0585 (10)
N21	0.0790 (3)	0.15794 (17)	0.20950 (19)	0.0409 (6)
C21	0.1656 (4)	0.1340 (2)	0.3023 (3)	0.0541 (9)
H21	0.1687	0.0682	0.3243	0.065*
O21	0.3758 (3)	0.35997 (15)	0.50108 (16)	0.0480 (5)
O22	0.3902 (3)	0.44629 (15)	0.34512 (17)	0.0468 (5)
C22	0.2501 (4)	0.2017 (2)	0.3666 (3)	0.0525 (9)
H22	0.3069	0.1817	0.4311	0.063*
C23	0.2502 (4)	0.2995 (2)	0.3350 (2)	0.0392 (7)
C24	0.1599 (4)	0.3245 (2)	0.2392 (3)	0.0520 (8)
H24	0.1560	0.3896	0.2146	0.062*
C25	0.0765 (4)	0.2528 (2)	0.1808 (3)	0.0503 (8)
H25	0.0149	0.2714	0.1177	0.060*
C26	0.3462 (4)	0.3749 (2)	0.3992 (2)	0.0397 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0532 (3)	0.0318 (2)	0.0380 (2)	−0.00216 (19)	−0.01220 (16)	−0.00046 (16)
N1	0.061 (2)	0.0587 (18)	0.076 (2)	0.0046 (16)	0.0107 (17)	−0.0018 (16)
C1	0.055 (2)	0.0454 (18)	0.070 (2)	−0.0019 (16)	0.0022 (19)	−0.0096 (16)
S1	0.0904 (9)	0.0886 (8)	0.0864 (8)	−0.0032 (7)	0.0312 (7)	−0.0235 (7)
O11	0.144 (3)	0.0572 (16)	0.0716 (18)	0.0320 (18)	−0.066 (2)	−0.0231 (14)
N11	0.0593 (19)	0.0640 (19)	0.0532 (17)	0.0088 (15)	−0.0147 (14)	0.0118 (14)
C11	0.078 (3)	0.066 (2)	0.056 (2)	−0.016 (2)	−0.031 (2)	0.0079 (18)
O12	0.100 (2)	0.0499 (14)	0.0645 (15)	0.0289 (14)	−0.0373 (15)	−0.0134 (12)
C12	0.077 (3)	0.0465 (18)	0.058 (2)	−0.0028 (18)	−0.0265 (19)	−0.0022 (15)
C13	0.0520 (19)	0.0437 (16)	0.0430 (16)	0.0054 (14)	−0.0095 (14)	−0.0023 (13)
C14	0.105 (3)	0.057 (2)	0.049 (2)	0.030 (2)	−0.031 (2)	−0.0147 (17)
C15	0.109 (4)	0.063 (2)	0.061 (2)	0.037 (2)	−0.023 (2)	−0.0084 (19)
C16	0.072 (2)	0.0440 (18)	0.0532 (19)	0.0084 (17)	−0.0277 (17)	−0.0045 (15)
N21	0.0492 (15)	0.0369 (13)	0.0350 (12)	−0.0022 (11)	−0.0040 (11)	−0.0004 (10)
C21	0.080 (2)	0.0332 (15)	0.0446 (17)	−0.0082 (15)	−0.0168 (16)	0.0043 (13)
O21	0.0702 (15)	0.0338 (10)	0.0367 (11)	−0.0032 (10)	−0.0108 (10)	−0.0008 (8)
O22	0.0565 (13)	0.0368 (11)	0.0444 (11)	−0.0065 (10)	−0.0086 (10)	0.0029 (9)
C22	0.076 (2)	0.0396 (16)	0.0373 (15)	−0.0055 (16)	−0.0168 (15)	0.0026 (12)
C23	0.0497 (18)	0.0340 (14)	0.0324 (14)	−0.0022 (13)	−0.0037 (13)	−0.0027 (11)
C24	0.066 (2)	0.0332 (15)	0.0518 (18)	−0.0011 (14)	−0.0194 (16)	0.0025 (13)
C25	0.063 (2)	0.0376 (16)	0.0458 (17)	0.0009 (15)	−0.0183 (15)	−0.0002 (13)
C26	0.0462 (17)	0.0309 (14)	0.0402 (15)	0.0021 (12)	−0.0054 (13)	−0.0014 (11)

Geometric parameters (Å, º) top

Co1—O22	2.004 (2)	C14—C15	1.364 (5)
Co1—O21ⁱ	2.004 (2)	C14—H14	0.9300
Co1—N1	2.010 (4)	C15—H15	0.9300
Co1—O12	2.097 (2)	N21—C25	1.331 (4)
Co1—N21ⁱⁱ	2.146 (2)	N21—C21	1.339 (4)
N1—C1	1.155 (5)	N21—Co1ⁱⁱⁱ	2.146 (2)
C1—S1	1.610 (4)	C21—C22	1.376 (4)
O11—C16	1.230 (4)	C21—H21	0.9300
N11—C15	1.316 (5)	O21—C26	1.261 (3)
N11—C11	1.318 (5)	O21—Co1ⁱ	2.004 (2)
N11—H1N	0.8600	O22—C26	1.253 (3)
C11—C12	1.373 (5)	C22—C23	1.379 (4)
C11—H11	0.9300	C22—H22	0.9300
O12—C16	1.242 (4)	C23—C24	1.388 (4)
C12—C13	1.366 (4)	C23—C26	1.495 (4)
C12—H12	0.9300	C24—C25	1.373 (4)
C13—C14	1.374 (5)	C24—H24	0.9300
C13—C16	1.514 (4)	C25—H25	0.9300

O22—Co1—O21ⁱ	136.53 (10)	N11—C15—H15	119.9
O22—Co1—N1	102.78 (12)	C14—C15—H15	119.9
O21ⁱ—Co1—N1	120.67 (12)	O11—C16—O12	128.1 (3)
O22—Co1—O12	94.28 (10)	O11—C16—C13	115.8 (3)
O21ⁱ—Co1—O12	84.54 (9)	O12—C16—C13	116.0 (3)
N1—Co1—O12	90.72 (13)	C25—N21—C21	116.7 (3)
O22—Co1—N21ⁱⁱ	90.97 (9)	C25—N21—Co1ⁱⁱⁱ	124.0 (2)
O21ⁱ—Co1—N21ⁱⁱ	91.26 (9)	C21—N21—Co1ⁱⁱⁱ	119.1 (2)
N1—Co1—N21ⁱⁱ	88.66 (12)	N21—C21—C22	123.3 (3)
O12—Co1—N21ⁱⁱ	174.71 (11)	N21—C21—H21	118.3
C1—N1—Co1	173.2 (3)	C22—C21—H21	118.3
N1—C1—S1	179.2 (4)	C26—O21—Co1ⁱ	130.33 (18)
C15—N11—C11	121.6 (3)	C26—O22—Co1	132.53 (19)
C15—N11—H1N	119.2	C21—C22—C23	119.7 (3)
C11—N11—H1N	119.2	C21—C22—H22	120.1
N11—C11—C12	120.6 (3)	C23—C22—H22	120.1
N11—C11—H11	119.7	C22—C23—C24	117.0 (3)
C12—C11—H11	119.7	C22—C23—C26	121.7 (3)
C16—O12—Co1	128.6 (2)	C24—C23—C26	121.4 (3)
C13—C12—C11	119.0 (3)	C25—C24—C23	119.7 (3)
C13—C12—H12	120.5	C25—C24—H24	120.2
C11—C12—H12	120.5	C23—C24—H24	120.2
C12—C13—C14	118.7 (3)	N21—C25—C24	123.5 (3)
C12—C13—C16	121.8 (3)	N21—C25—H25	118.2
C14—C13—C16	119.4 (3)	C24—C25—H25	118.2
C15—C14—C13	119.8 (3)	O22—C26—O21	126.8 (3)
C15—C14—H14	120.1	O22—C26—C23	116.0 (2)
C13—C14—H14	120.1	O21—C26—C23	117.2 (3)
N11—C15—C14	120.1 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H1N···O11^iv	0.86	1.80	2.561 (4)	147

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

Experimental details

Crystal data
Chemical formula	[Co(C₆H₅NO₂)(NCS)(C₆H₄NO₂)]
M_r	362.22
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	8.7857 (7), 13.5401 (8), 12.2054 (9)
β (°)	95.740 (6)
V (Å³)	1444.67 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.35
Crystal size (mm)	0.18 × 0.13 × 0.04

Data collection
Diffractometer	Stoe IPDS2 diffractometer
Absorption correction	Numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008)
T_min, T_max	0.808, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	12489, 2844, 2353
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.098, 1.13
No. of reflections	2844
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.39

Computer programs: X-AREA (Stoe & Cie, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2011), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Co1—O22	2.004 (2)	Co1—O12	2.097 (2)
Co1—O21ⁱ	2.004 (2)	Co1—N21ⁱⁱ	2.146 (2)
Co1—N1	2.010 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H1N···O11ⁱⁱⁱ	0.86	1.80	2.561 (4)	147.1

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

Acknowledgements

We gratefully acknowledge financial support by the DFG (project No. NA 720/3–1) and the State of Schleswig–Holstein. We thank Professor Dr Wolfgang Bensch for access to his experimental facilities.

References

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