Poly[bis­(methanol-κO)tris­(μ-pyrimidine-κ2N:N′)tetra­kis(thio­cyanato-κN)dinickel(II)]

Wriedt, M.; Sellmer, S.; Jess, I.; Näther, C.

doi:10.1107/S1600536809005674

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Pages m361-m362

doi:10.1107/S1600536809005674

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Poly[bis(methanol-κO)tris(μ-pyrimidine-κ²N:N′)tetrakis(thiocyanato-κN)dinickel(II)]

Mario Wriedt,^a Sina Sellmer,^a Inke Jess ^a and Christian Näther ^a ^*

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

(Received 12 February 2009; accepted 17 February 2009; online 6 March 2009)

In the crystal structure of the title compound, [Ni₂(NCS)₄(C₄H₄N₂)₃(CH₃OH)₂]_n, each nickel(II) cation is coordinated by three N-bonded pyrimidine ligands, two N-bonded thiocyanate anions and one O-bonded methanol molecule in a distorted octahedral environment. The asymmetric unit consists of one nickel cation, two thiocyanate anions and one methanol molecule in general positions, as well as one pyrimidine ligand located around a twofold rotation axis. The crystal structure consists of μ-N:N′ pyrimidine-bridged zigzag-like nickel thiocyanate chains; these are further linked by μ-N:N-bridging pyrimidine ligands into layers which are stacked perpendicular to the b axis. The layers are connected via weak O—H⋯S hydrogen bonding.

Related literature

For related pyrimidine structures, see: Lloret et al. (1998 ); Näther et al. (2007 ); Näther & Greve (2003 ). For general background, see: Wriedt et al. (2008 ) and literature cited therein.

Experimental

Crystal data

[Ni₂(NCS)₄(C₄H₄N₂)₃(CH₄O)₂]
M_r = 654.10
Orthorhombic, F d d 2
a = 20.0624 (4) Å
b = 32.5018 (6) Å
c = 8.0268 (2) Å
V = 5233.99 (19) Å³
Z = 8
Mo Kα radiation
μ = 1.80 mm⁻¹
T = 80 K
0.19 × 0.09 × 0.03 mm

Data collection

Stoe IPDS-2 diffractometer
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008 ) T_min = 0.813, T_max = 0.936
26228 measured reflections
3743 independent reflections
3659 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.020
wR(F²) = 0.048
S = 1.09
3743 reflections
170 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 1746 Friedel pairs
Flack parameter: 0.092 (7)

Table 1
Selected geometric parameters (Å, °)

Ni1—N31	2.0334 (14)
Ni1—N21	2.0376 (13)
Ni1—O41	2.1053 (12)
Ni1—N11	2.1118 (13)
Ni1—N2ⁱ	2.1200 (13)
Ni1—N1	2.1244 (13)
Symmetry code: (i) $[-x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O41—H1O4⋯S21ⁱⁱ	0.80 (3)	2.50 (3)	3.2474 (14)	154 (2)
Symmetry code: (ii) $[x+{\script{1\over 4}}, -y+{\script{1\over 4}}, z+{\script{1\over 4}}]$ .

Data collection: X-AREA (Stoe & Cie, 2008); cell refinement: X-AREA; data reduction: X-RED32 (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); software used to prepare material for publication: XCIF in SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809005674/si2156sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809005674/si2156Isup2.hkl

checkCIF report

Comment top

Recently, we have shown that new ligand deficient coordination polymers with interesting magnetic properties can be prepared by thermal decomposition of suitable ligand rich precursor compounds (Näther & Greve, 2003; Wriedt et al., 2008; and Näther et al., 2007). In our ongoing investigation on the synthesis, structures and properties of new coordination polymers based on paramagnetic metal pseudohalides and N-donor ligands (Lloret et al. 1998), we have reacted nickel(II) thiocyanate with pyrimidine in methanol. In this reaction single crystals of the title compound has been formed.

The 2:3 title compound [Ni(SCN)₂(pyrimidine)₃*2MeOH]_n (Fig. 1) represents a two-dimensional coordination polymer, which consists of µ-1,3-(N,N) pyrimidine bridged zigzag like nickel thiocyanates chains, which are further linked by µ-1,3-(N,N) bridged pyrimidine ligands into layers (Fig. 2 and 3). Within each layer the nickel cations are bridged by three µ-1,3-(N,N') pyrimidine ligands and are further terminal coordinated by two N-bonded thiocyanate anions and one O-bonded methanol molecule. Thus, each nickel cation is octahedrally coordinated. The asymmetric unit consists of one nickel cation, two thiocyanate anions and one methanol molecule in general position as well as one pyrimidine ligand located around a twofold rotation axis. The Ni—NCS distances amount to 2.0334 (14) and 2.0376 (13) Å and the Ni—N_pyrimidine distances range from 2.1118 (13) to 2.1244 (13) Å as well as the angles around the iron cations range between 86.62 (5) and 177.66 (5)° (Tab. 1). The shortest intra- and interchain Ni···Ni distances amount to 5.9470 (1) and 8.4023 (1) Å, respectively.

Related literature top

For related pyrimidine structures, see: Lloret et al. (1998); Näther et al. (2007); Näther & Greve (2003). For general background, see: Wriedt et al. (2008) and literature cited therein.

Experimental top

Ni(SCN)₂, pyrimidine and methanol were obtained from Alfa Aesar. 0.125 mmol (21.5 mg) Ni(SCN)₂, 0.25 mmol (20.0 mg) pyrimidine and 0.5 ml methanol were transfered in a closed test-tube. The mixture was heated at 120 °C for three days. After cooling green needle-shaped single crystals of the title compound were obtained in a heterogenous mixture.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2008); cell refinement: X-AREA (Stoe & Cie, 2008); data reduction: X-RED32 (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); software used to prepare material for publication: XCIF in SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Crystal structure of the title compound with labelling and displacement ellipsoids drawn at the 50% probability level. [Symmetry codes: (i) -x+1, -y+1/2, z+1/2; (ii) -x+3/2, -y+1/2, z.]
	Fig. 2. The crystal structure of the title compound with view along the b axis.
	Fig. 3. The crystal structure of the title compound with view along the c axis.

Poly[bis(methanol-κO)tris(µ-pyrimidine- κ²N:N')tetrakis(thiocyanato-κN)dinickel(II)] top

Crystal data top

[Ni₂(NCS)₄(C₄H₄N₂)₃(CH₄O)₂]	F(000) = 2672
M_r = 654.10	D_x = 1.660 Mg m⁻³
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 26829 reflections
a = 20.0624 (4) Å	θ = 2.4–30.2°
b = 32.5018 (6) Å	µ = 1.80 mm⁻¹
c = 8.0268 (2) Å	T = 80 K
V = 5233.99 (19) Å³	Needle, green
Z = 8	0.19 × 0.09 × 0.03 mm

Data collection top

Stoe IPDS-2 diffractometer	3743 independent reflections
Radiation source: fine-focus sealed tube	3659 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ω scans	θ_max = 29.8°, θ_min = 2.4°
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008)	h = −28→28
T_min = 0.813, T_max = 0.936	k = −45→45
26228 measured reflections	l = −11→11

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.020	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.048	w = 1/[σ²(F_o²) + (0.0258P)² + 3.6623P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.001
3743 reflections	Δρ_max = 0.34 e Å⁻³
170 parameters	Δρ_min = −0.21 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1746 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.0917 (74)

Crystal data top

[Ni₂(NCS)₄(C₄H₄N₂)₃(CH₄O)₂]	V = 5233.99 (19) Å³
M_r = 654.10	Z = 8
Orthorhombic, Fdd2	Mo Kα radiation
a = 20.0624 (4) Å	µ = 1.80 mm⁻¹
b = 32.5018 (6) Å	T = 80 K
c = 8.0268 (2) Å	0.19 × 0.09 × 0.03 mm

Data collection top

Stoe IPDS-2 diffractometer	3743 independent reflections
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008)	3659 reflections with I > 2σ(I)
T_min = 0.813, T_max = 0.936	R_int = 0.043
26228 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.020	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.048	Δρ_max = 0.34 e Å⁻³
S = 1.09	Δρ_min = −0.21 e Å⁻³
3743 reflections	Absolute structure: Flack (1983), 1746 Friedel pairs
170 parameters	Absolute structure parameter: 0.0917 (74)
1 restraint

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
Ni1	0.606548 (9)	0.227000 (5)	0.78384 (2)	0.01902 (4)
N1	0.55175 (7)	0.27249 (4)	0.65206 (17)	0.0215 (2)
N2	0.47332 (7)	0.29025 (4)	0.44204 (17)	0.0223 (2)
C1	0.50701 (7)	0.26330 (4)	0.5344 (2)	0.0221 (2)
H1	0.4985	0.2350	0.5149	0.026*
C2	0.48569 (8)	0.33035 (5)	0.4691 (2)	0.0254 (3)
H2	0.4634	0.3505	0.4036	0.030*
C3	0.52997 (9)	0.34281 (5)	0.5898 (2)	0.0270 (3)
H3	0.5379	0.3712	0.6103	0.032*
C4	0.56250 (9)	0.31286 (5)	0.6799 (2)	0.0256 (3)
H4	0.5933	0.3208	0.7638	0.031*
N11	0.69268 (6)	0.24119 (4)	0.64396 (16)	0.0216 (2)
C11	0.7500	0.2500	0.7204 (3)	0.0221 (4)
H11	0.7500	0.2500	0.8388	0.027*
C13	0.7500	0.2500	0.3882 (3)	0.0322 (5)
H13	0.7500	0.2500	0.2698	0.039*
C14	0.69298 (8)	0.24151 (6)	0.4778 (2)	0.0275 (3)
H14	0.6528	0.2357	0.4196	0.033*
N21	0.58003 (7)	0.18291 (4)	0.61601 (18)	0.0257 (3)
C21	0.55990 (7)	0.15388 (4)	0.5486 (2)	0.0223 (3)
S21	0.53215 (3)	0.113396 (13)	0.45037 (6)	0.03346 (9)
N31	0.63443 (7)	0.26781 (4)	0.96274 (18)	0.0249 (3)
C31	0.63460 (8)	0.29113 (5)	1.07238 (19)	0.0228 (3)
S31	0.63423 (3)	0.323347 (15)	1.22718 (6)	0.03821 (11)
O41	0.66278 (7)	0.18126 (4)	0.90523 (16)	0.0300 (3)
C41	0.67557 (12)	0.17680 (6)	1.0780 (3)	0.0418 (5)
H41A	0.6591	0.2011	1.1375	0.063*
H41B	0.7237	0.1740	1.0962	0.063*
H41C	0.6528	0.1522	1.1198	0.063*
H1O4	0.6830 (14)	0.1640 (8)	0.854 (3)	0.047 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.01457 (7)	0.02028 (8)	0.02220 (8)	−0.00051 (7)	−0.00029 (7)	−0.00255 (7)
N1	0.0171 (6)	0.0219 (6)	0.0254 (6)	−0.0014 (4)	−0.0012 (4)	0.0006 (5)
N2	0.0169 (6)	0.0217 (5)	0.0282 (6)	−0.0005 (5)	−0.0006 (5)	0.0003 (5)
C1	0.0175 (6)	0.0196 (5)	0.0291 (6)	−0.0006 (4)	−0.0011 (6)	−0.0018 (6)
C2	0.0253 (8)	0.0222 (6)	0.0287 (7)	0.0000 (5)	0.0014 (6)	0.0019 (6)
C3	0.0329 (9)	0.0193 (6)	0.0287 (7)	−0.0039 (6)	0.0002 (6)	−0.0016 (5)
C4	0.0276 (8)	0.0239 (6)	0.0254 (7)	−0.0048 (6)	−0.0021 (6)	−0.0014 (5)
N11	0.0165 (6)	0.0253 (6)	0.0231 (6)	−0.0003 (5)	0.0005 (5)	−0.0011 (4)
C11	0.0173 (9)	0.0262 (9)	0.0230 (9)	0.0002 (7)	0.000	0.000
C13	0.0257 (12)	0.0499 (15)	0.0208 (10)	−0.0044 (10)	0.000	0.000
C14	0.0202 (7)	0.0376 (8)	0.0247 (7)	−0.0016 (6)	−0.0022 (6)	−0.0019 (6)
N21	0.0230 (6)	0.0245 (6)	0.0296 (7)	−0.0003 (5)	−0.0028 (5)	−0.0053 (5)
C21	0.0183 (6)	0.0246 (6)	0.0239 (6)	0.0029 (5)	0.0015 (5)	0.0018 (5)
S21	0.0355 (2)	0.02680 (18)	0.0381 (2)	−0.00436 (16)	−0.00331 (18)	−0.00964 (16)
N31	0.0222 (6)	0.0263 (6)	0.0262 (6)	−0.0024 (5)	0.0006 (5)	−0.0035 (5)
C31	0.0177 (6)	0.0241 (6)	0.0265 (8)	−0.0009 (5)	0.0005 (5)	0.0012 (5)
S31	0.0431 (3)	0.0360 (2)	0.0355 (2)	−0.00220 (19)	0.00501 (19)	−0.01510 (18)
O41	0.0285 (6)	0.0306 (6)	0.0308 (6)	0.0096 (5)	−0.0014 (5)	0.0020 (5)
C41	0.0516 (12)	0.0336 (9)	0.0403 (10)	0.0021 (8)	−0.0217 (9)	0.0030 (7)

Geometric parameters (Å, º) top

Ni1—N31	2.0334 (14)	N11—C14	1.334 (2)
Ni1—N21	2.0376 (13)	N11—C11	1.3346 (16)
Ni1—O41	2.1053 (12)	C11—N11ⁱⁱⁱ	1.3346 (16)
Ni1—N11	2.1118 (13)	C11—H11	0.9500
Ni1—N2ⁱ	2.1200 (13)	C13—C14	1.379 (2)
Ni1—N1	2.1244 (13)	C13—C14ⁱⁱⁱ	1.379 (2)
N1—C1	1.337 (2)	C13—H13	0.9500
N1—C4	1.348 (2)	C14—H14	0.9500
N2—C1	1.332 (2)	N21—C21	1.160 (2)
N2—C2	1.3444 (19)	C21—S21	1.6320 (16)
N2—Ni1ⁱⁱ	2.1200 (13)	N31—C31	1.161 (2)
C1—H1	0.9500	C31—S31	1.6250 (16)
C2—C3	1.376 (2)	O41—C41	1.418 (2)
C2—H2	0.9500	O41—H1O4	0.80 (3)
C3—C4	1.377 (2)	C41—H41A	0.9800
C3—H3	0.9500	C41—H41B	0.9800
C4—H4	0.9500	C41—H41C	0.9800

N31—Ni1—N21	176.02 (6)	C4—C3—H3	121.0
N31—Ni1—O41	89.22 (6)	N1—C4—C3	121.66 (15)
N21—Ni1—O41	87.09 (5)	N1—C4—H4	119.2
N31—Ni1—N11	90.45 (5)	C3—C4—H4	119.2
N21—Ni1—N11	90.90 (6)	C14—N11—C11	117.02 (16)
O41—Ni1—N11	87.81 (5)	C14—N11—Ni1	122.48 (11)
N31—Ni1—N2ⁱ	87.56 (5)	C11—N11—Ni1	120.49 (12)
N21—Ni1—N2ⁱ	90.73 (5)	N11—C11—N11ⁱⁱⁱ	125.2 (2)
O41—Ni1—N2ⁱ	86.62 (5)	N11—C11—H11	117.4
N11—Ni1—N2ⁱ	174.11 (5)	N11ⁱⁱⁱ—C11—H11	117.4
N31—Ni1—N1	92.29 (5)	C14—C13—C14ⁱⁱⁱ	117.1 (2)
N21—Ni1—N1	91.44 (5)	C14—C13—H13	121.4
O41—Ni1—N1	177.66 (5)	C14ⁱⁱⁱ—C13—H13	121.4
N11—Ni1—N1	90.39 (5)	N11—C14—C13	121.79 (16)
N2ⁱ—Ni1—N1	95.23 (5)	N11—C14—H14	119.1
C1—N1—C4	116.23 (14)	C13—C14—H14	119.1
C1—N1—Ni1	122.94 (10)	C21—N21—Ni1	166.20 (14)
C4—N1—Ni1	120.79 (11)	N21—C21—S21	178.86 (16)
C1—N2—C2	117.01 (14)	C31—N31—Ni1	164.08 (13)
C1—N2—Ni1ⁱⁱ	122.90 (10)	N31—C31—S31	179.26 (16)
C2—N2—Ni1ⁱⁱ	119.50 (11)	C41—O41—Ni1	128.45 (12)
N2—C1—N1	125.96 (13)	C41—O41—H1O4	110 (2)
N2—C1—H1	117.0	Ni1—O41—H1O4	121.7 (19)
N1—C1—H1	117.0	O41—C41—H41A	109.5
N2—C2—C3	121.22 (15)	O41—C41—H41B	109.5
N2—C2—H2	119.4	H41A—C41—H41B	109.5
C3—C2—H2	119.4	O41—C41—H41C	109.5
C2—C3—C4	117.90 (14)	H41A—C41—H41C	109.5
C2—C3—H3	121.0	H41B—C41—H41C	109.5

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O41—H1O4···S21^iv	0.80 (3)	2.50 (3)	3.2474 (14)	154 (2)

Symmetry code: (iv) x+1/4, −y+1/4, z+1/4.

Experimental details

Crystal data
Chemical formula	[Ni₂(NCS)₄(C₄H₄N₂)₃(CH₄O)₂]
M_r	654.10
Crystal system, space group	Orthorhombic, Fdd2
Temperature (K)	80
a, b, c (Å)	20.0624 (4), 32.5018 (6), 8.0268 (2)
V (Å³)	5233.99 (19)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.80
Crystal size (mm)	0.19 × 0.09 × 0.03

Data collection
Diffractometer	Stoe IPDS2 diffractometer
Absorption correction	Numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008)
T_min, T_max	0.813, 0.936
No. of measured, independent and observed [I > 2σ(I)] reflections	26228, 3743, 3659
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.699

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.020, 0.048, 1.09
No. of reflections	3743
No. of parameters	170
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.21
Absolute structure	Flack (1983), 1746 Friedel pairs
Absolute structure parameter	0.0917 (74)

Computer programs: X-AREA (Stoe & Cie, 2008), X-RED32 (Stoe & Cie, 2008, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), XCIF in SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Ni1—N31	2.0334 (14)	Ni1—N11	2.1118 (13)
Ni1—N21	2.0376 (13)	Ni1—N2ⁱ	2.1200 (13)
Ni1—O41	2.1053 (12)	Ni1—N1	2.1244 (13)

N31—Ni1—N21	176.02 (6)	O41—Ni1—N1	177.66 (5)
O41—Ni1—N2ⁱ	86.62 (5)	N2ⁱ—Ni1—N1	95.23 (5)
N11—Ni1—N2ⁱ	174.11 (5)

Symmetry code: (i) −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
O41—H1O4···S21ⁱⁱ	0.80 (3)	2.50 (3)	3.2474 (14)	154 (2)

Symmetry code: (ii) x+1/4, −y+1/4, z+1/4.

Acknowledgements

MW thanks the Stiftung Stipendien-Fonds des Verbandes der Chemischen Industrie and the Studienstiftung des deutschen Volkes for a PhD scholarship. We gratefully acknowledge financial support by the State of Schleswig-Holstein and we thank Professor Dr Wolfgang Bensch for the opportunity to use of his experimental facility.

References

Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
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