Synthesis and crystal structure of the 1-dimensional dihalide-bridged polymers:...

Po/yhedron Vol. 17, Nos. 11-12, pp. 1843-1850, 1998

Pergamon PII : SO277-5387(97)00521-

IC 1998 Elsevier Science Ltd All rights reserved. Printed in Great Britarn

0277-5387/9X $19.00+0.00

Synthesis and crystal structure of the l- dimensional dihalide-bridged polymers :

dichlorobis(thiazole)iron(II) and dibromobis(thiazole)copper(II)

Michael James,* Hiroyuki Kawaguchi and Kazuyuki Tatsumi

Department of Chemistry, Faculty of Science, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-01, Japan

(Received 7 November 1997 ; accepted 11 December 1997)

Abstract-The new polymeric compound Fe(thiazole),Cl, (1) has been synthesised by the addition of thiazole to an ethanolic solution of anhydrous FeCl,. The structure of Cu(tz)*Br, (2) has also been determined. The structures of both polymers consist of pseudo-octahedral units, doubly linked by halide-bridges to form infinite linear chains. Slight variation in the bonding of the two are observed, relating to the Jahn-Teller nature of Cu*+. Room temperature magnetic susceptibility measurements of 1 give an effective moment of 5.51(2) B.M., indicating high-spin Fe(H). 0 1998 Elsevier Science Ltd. All rights reserved

Keywords: dichlorobis(thiazole)iron(II); dibromobis(thiazole)copper(II).

Polymeric systems of Cu and Co containing thiazole (tz) and di-bridging chloro ligands have been known for some time; however, only the structure of dichlorobis(thiazole)copper(II) has previously been reported [l]. Prior studies of the reaction between thiazole and iron(H) chloride have indicated an analogous compound is formed [2], however thus far no structural data have been reported. This paper details the synthesis and structural characterisation of the iron analogue Fe(tz)&l, (1) by single crystal techniques, as well as the structural characterisation of the previously prepared Cu(tz),Br, (2). Room temperature magnetic properties of 1 are presented.

EXPERIMENTAL

Anhydrous CuBr, (99% purity), anhydrous FeCl, (98% purity) and thiazole (99% purity) were obtained from Aldrich Chemical Co. Inc. and used as obtained. Ethanol and methylene chloride (A.R. grade) were

*Author to whom correspondence should be addressed: Neutron Scattering Group, ANSTO, Lucas Heights Research Laboratories, PMB 1, Menai NSW 2234, Australia. Fax: 612-9717 3606. E-mail: [email protected]

used when freshly distilled. The synthesis of 1 was carried out under dry Ar using Schlenk techniques, while 2 was prepared in air. Elemental analyses were carried out on a LECO CHNS-900 elemental analyser. Infrared spectra were recorded (Nujol mull) in the 350-5200 cm-’ range on a Perkin-Elmer FT-IR 2000 spectrophotometer. Magnetic susceptibility measurements were carried out at room temperature using a Sherwood Scientific Gouy balance.

Fe(tz),Cl (1)

Thiazole (12 mmol, 2 ml) was added to an ethanolic solution of anhydrous FeC& (6 mmol, 16 ml) with constant stirring. A pale yellow precipitate was immediately formed. The sample was stirred for a further 10 min before being centrifuged. The super- natant was reduced to N 10 ml under vacuum and stored in a sealed vessel under dry Ar. Yellow crystals suitable for X-ray diffraction were obtained after 8 weeks. The microcrystalline precipitate was washed with benzene and diethyl ether. Found : C, 24.6 ; H, 2.0; N, 9.4; S, 21.6%. Calcd for 1: C, 24.7; H, 2.0; N, 9.1 ; S, 21.2%. IR (nujol) : v(ligand) 608 (m), 737 (m), 808 (m), 879 (w), 912 (w), 1060 (w), 1112 (w), 1231 (w) cm-‘.

1843

1844 M. James et al

Wt&Br2 (2)

Thiazole (12 mmol, 2 ml) was added to an ethanolic solution of anhydrous CuBr, (6 mmol, 16 ml) with constant stirring. A green precipitate was immediately formed. The sample was stirred for 20 min, collected, washed with ether and benzene and allowed to dry under suction. The product was recrystallised from dimethylformanide by addition of an equal volume of methylene chloride followed by cooling in the freezer compartment of a refrigerator. Dark green needle-like crystals suitable for X-ray diffraction were obtained after 3 weeks. Found: C, 18.5; H, 1.6; N. 6.9; S, 16.6%.Calcdfor2:C,l8.3;H, 1.5;N,7.1;!$ 16.3%. IR (Nujol): v(ligand) 612 (s), 635 (w), 738 (s), 810 (s), 882 (m), 920 (m), 1065 (m), 1113 (m), 1237 (m) cm-‘.

X-ray crystallogruphy

Measurements were made on a Rigaku AFC7R diffractometer an ambient temperature using mon- ochromated MO-K, radiation (3, = 0.71069 A). Crys- tals were mounted on the top of glass fibers. Cell constants were obtained by least-squares analysis of 16 strong reflections in the range 5.53 < 20 < 14.33” for 1, and 25 reflections (29.35” < 20 < 29.79 ) for 2. Details of crystal data, data collection and structure refinement for 1 and 2 are summarised in Table 1. The intensity data were corrected for Lorentz and polarisation effects and an empirical absorption cor-

rection based on azimuthal scans of several reflections was also applied.

The structures were solved by direct methods and developed by alternating cycles of difference Fourier syntheses and full matrix least-squares refinements, The positions of the non-hydrogen atoms were determined unequivocally, with the exception of the thiazole ligands in 1, which displayed static disorder between adjacent carbon and sulfur sites, due to a 180” rotation about its Fe-N bonds. In this case the disorder was modeled by refinement of jointly occupied S/C sites. The minority components of these jointly occupied sites are indicated by a primed label, such that the site S/C’ contains a majority of sulfur, while the adjacent C/S’ site is constrained so as to give an equal proportion of carbon. The occupation factors of sulfur atoms were refined only at the S/C’ sites, while the C’ and S’ occupation factors were constrained so as to give fully occupied sites. The non- hydrogen atoms were refined anisotropically, with the exception of the atoms at the disordered sites which were refined isotropically. Hydrogen atoms were placed at calculated positions. Neutral atom scattering factors were taken from [3], and anomalous dispersion corrections were taken from [4]. Crys- tallographic calculations were carried ut with a teXsan crystallographic software package of Molecular Structure Corporation (1985 & 1992).

RESULTS AND DISCUSSION

The chemical reactivity of iron chloride with thiazole does not appear to be substantially different

Table 1. Summary of crystallographic data for Fe(tz),Clz (1) and Cu(tz),Br, (2)

1 2

Formula C,H,NZFeS,C12 Formula weight 297.012 Crystal system Monoclinic Space group Cc (No. 9) a (A) 17.908(9) b (A) 3.717(5) c (A) 14.870(8) B (“) 95.30(5) V(A’) 985(l) Z 4 Colour, Habit Yellow, needle D, (g cm-‘) 2.001 p (MO-K,), cm-’ 24.42

2&,,, deg 55.0 No. of reflns used I > 30(1)) 1005 P,,.~P~,,, e A-’ 0.47/ - 0.59 R”/R,.h, % 3.214.8 GOF 2.33

C,H,N2CuSZBr, 393.614 Monoclinic P2,/c (No. 14) 7.460(2) 3.987(3) 17.757(2) 92.15(l) 527.8(3) L

Dark green, needle 2.476 100.10 55.0 1387 0.45/- 1.09 2.913.6 1.59

Synthesis and crystal structures of di-bridged polymers 1845

to that observed for copper(H) halides [I]. While compounds of M(H)-thiazole-halides (M = Co, Ni, Cu, Zn and Pd) have been known for some time [5,6], thiazole containing complexes of Fe(I1) have only recently been reported [2,7].

Crystal structure ~f‘Fe(tz),CI, (1)

The structure of Fe(tz),Cl, (1) consists of tetra- gonally elongated octahedral units, with N-donor thiazole ligands in the axial positions. These units are equatorially linked along the b-axis by double chloride bridges to form infinite linear chains (Fig. 1). The packing of these chains in the unit cell of 1 is shown in Fig. 2. Selected bond lengths and bond angles for 1 are given in Table 2.

Four distinct Fe-Cl bonds are formed in 1 with roughly equivalent bond lengths ranging between 2.521(2) A and 2.560(2) A, which bridge a Fe-Fe distance of 3.717(5) A. Fe-N bond lengths of 2.196(6) A (Fe-Nl) and 2.150(7) A (Fe-N2) are typical of those found for the Fe(II)-N bonds (2.21(l) A) in the complex salt [Fe(tz),][Fe,OCl,] [7]. The bond angles about Fe in 1 give rise to a pseudo- octahedrally coordinated centre that shows deviations away from regular angles (Table 2). Angles between equivalent chlorine atoms such as Cl l-Fe-Cl 1* were found to be -94”, while those between inequi- valent chlorine atoms such as Cl I*-Fe-Cl2 were

found to be -86”. The axial Nl-Fe-N2 bond angle (177.4(3)“) also shows a deviation away from regular symmetry.

Constrained refinement of occupation factors for the disordered thiazole ring (N2-C4-C5-S2-C6) revealed that the S2 and C5 sites (as shown in Figs 1 and 2) were approximately 87% occupied with the designated atoms. The C5’ and S2’ atoms that were generated by the 180” rotation about the Fe-N2 bond occupied the remaining 13% of these sites. Orientational static disorder of this type has been previously reported for trans-Mo(tz),Br, [23] and FezO(tz),Cl, [2].

The dimensions of the non-disordered thiazole ligand in 1 are typical of those found in other metal thiazole complexes [ 1,2,7,23]. The axial thiazole ligands of 1 show rotations about their Fe-N bonds with respect to one another (Fig. 1). The thiazole rings Nl-Cl-C2-Sl-C3 (i.e. those labeled A, B, D and F in Fig. 2) are rotated approximately 15” away from the ac plane, while the rings N2-C4-C5-S2-C6 (C, E, G and H) are rotated approximately 25” in the opposite direction. The sense of tilting of the thiazole rings in Fig. 2 is indicated such that atoms labeled “ + ” are positioned above the ac plane, while “ - ” atoms are positioned below.

The crystal structures of a number of polymeric iron(I1) compounds have been documented. Of these, the majority are comprised of 0- [8-151 or N-donor

Fig. 1. An ORTEP drawing of linear chains of Fe(tz),Cl, (1). H atoms are omitted for clarity. All atoms are represented by the thermal ellipsoids at 50% probability.

1846 M. James er al.

C

L a

m S-44

Fig. 2. Packing of infinite linear chains in the unit cell of Fe(tL)ZC12 (1). The chain direction is into h-axis).

\ <-lOl>

the page (parallel to the

[16-211 bridging ligands. Polymeric iron complexes based on l-dimensional di-bridging halide chains are almost unknown. A notable example is that of [FeCl,(OPMe,)], [22], where each iron centre is linked by 2 axial and 2 equatorial bridging chlorine atoms to adjacent iron atoms. The -0PMe; group adopts a third equatorial position about the Fe atom, leading to a distorted trigonal bipyramidal coordination geometry. Thus, while [FeCL(OPMe,], is also a dichloride bridged iron(I1) polymer, the bonding relationship between adjacent molecular units is substantially different to that observed in 1.

A much wider range of Fe-Cl bond lengths (2.350 A-2.603 A) are observed in the more highly distorted Fe&Y, chains of [FeCL(OPMe,)], [22]. The Fe-Fe bond lengths for this complex (3.688(l) A and 3.560(l) A) are also slightly shorter than that found in 1. The axial Cl-Fe-Cl bond angles of

[FeCI,(OPMe,)],, are similar (174.14(3)’ ) to those in I, however, by virtue ofthe trigonal bipyramidal coordination. the equatorial Cl-Fe-Cl bond angle (123.49(3) ) is substantially different.

The polymeric compound Cu(tz),Br, (2) consists of the same dihalide bridged linear structure as 1 and has been found to be isostructural with Cu(tz),C& [I]. The chain structure of 2 is shown in Fig. 3 and the packing of chains in the unit cell is displayed in Fig. 4. Selected bond lengths and bond angles are given in Table 3. The Cu:Br? structural motif based-on di-bridging bro- mide ligands has been observed in numerous Cu(1) and Cu(II) polymeric complexes [2&32]. In particular the complexes Cu(3,5-dimethylpyridine),BrZ [24],

Synthesis and crystal structures of di-bridged polymers

Table 2. Selected bond lengths (A) and angles ( ) for 1

1847

Fe-Fe*“ Fe-C I 1 Fe-Gil” Fe-N 1 NILCI Cl--s1 S2-C? c2-c3 C3-N I

N I-Fe-N2 Fe-C I 1 -Fe* Cl I-Fe-Cl I* Cl I*-Fe-Cl2* ClI*-Fe-Cl2 Cl I-Fe-N1 Cl 1 *-Fe-N 1 Cl I-Fe-N2 Cl 1 *-Fe-N2 Fe-N 1 -C 1 N I-Cl-SI c1-sI-c2 s I -c2-c3 C2-C3-N I Fe-N l-C3

3.717(5) 2.560(2) 2.521(2) 2.196(6) I .345(9) 1.750(7) 1.739(7) 1.32(l) 1.31(l)

177.4(3) 94.1(l) 94.0( 1)

179. I (I) 86.1(4) 90.4(2) 90.9(2) 91.6(2) 90.7(2)

119.2(4) 111.5(5) 90.0(3)

106.4(6) 121.8(S) 131.0(5)

Fe-C 12 Fe-C l2* Fe-N2 N2-C4 C4-S2’CSh S2,‘C5’-C51S2’ C5:S2’-C6 C6-N2

Fe-C 12-Fe* C 12-Fe-C 12* Cl i-Fe-Cl2 Cl I-Fe-Cl2” C12-Fe-N2 C 12*-Fe-N2 C 12-Fe-N 1 C 12*-Fe-N 1 Fe-N2-C4 N2-C4-S2!‘C5’ C4-S2;C5’-C5,iS2’ S2,!C5’-C5:‘S2’-C6 C5:S2’-C6-N2 Fe-N2-C6

2.539(2) 2.527(2) 2.150(7) 1.29(l) 1.630(9) 1.663(3) 1.465(9) 1.451(X)

94.4(l) 94.4(l)

179.5(l) 85.5(l) 88.6(2) 89.6(2) 89.4(2) 88.9(2)

131.0(5) Il9.5(6) 92.3(3)

109.2(3) 110.2(5) 120.4(4)

“An asterisk denotes a translation of the molecule along the h axis. ‘Sites disordered by 180 rotations about the Fe-N2 bond, with occupancy factors

of S2:C5’ and C5:S2’ = 0.87(1)/0.13.

Cu(pyridine), - BrZ PI and Cu(N-methyl- imidazole),Br? [26] show essentially isostructural fea- tures to 2 with a rrans-arrangement of Cu-N bonds and di-bridging Br-Cu-Br* bonds. The Cu-N distance in 2 of I .988(3) 8, is essentially identical to that found in the chloro- analogue (1.990(2) A). while the disparate Cu-Br distances of 2.472( I ) A and 3.120( 1) A are also consistent with those observed for Cu(tz),Cl, (2.322(l) A and 2.998(l) A). The essentially regular Br-Cu-Br* angles of 90.2(l) are in agreement with those observed for other dibromo- bridged copper complexes [2&26].

The structure of 1 is analogous to these Cu(tz)zXz (X = Cl and Br) polymers in that it contains a similar di-bridging linear chain structure along the h-axis. Closer examination of Figs 1 and 3 however, indicate slightly different structural behaviour, suggesting dissimilar bonding mechanisms in 1 and 2. In contrast to the opposed rotational behaviour of the thiazole rings in I. the rings in 2 show synchronised rotations about their Cu-N bonds of approximately 21 ’ relative to the uc plane (Figs 3 and 4). These distinct rotational behaviours are clearly linked to the different transition metal-halide bonding modes in these complexes. Estes and coworkers [I] described the polymer structure of Cu(tz),Clz as a square-planar array consisting of two thiazole ligands and two short in-plane chloride bonds linked by the two longer out-

of-plane Cu-Cl bonds. The bonding arrangement in 2 can also be described in this matter and is reflective of the Jahn-Teller nature of d’ Cu’+. Given the in- plane nature of the strongest bonds about the Cu centre, it is likely that the single-ion ground state is essentially d,~_,l in character.

Examination of the bonding picture about the Fe centre of 1 indicates a much more regular arrangement in terms of the Fe-N and Fe-Cl bond lengths. The square-planar-like arrangement of two halide and two nitrogen bonds, along with the two longer out-of- plane halide bonds that is observed in 2 is inap- propriate for describing I, where very little variation is shown between each of the four of the Fe-Cl bonds. The pseudo-octahedral arrangement described above provides a more suitable description, given that Jahn-Teller effects do not contribute significantly to the high-spin dh ground state configuration of Fe”

Comparison of the tilting of the thiazole rings across the iron and copper transition metal centres (Figs 2 and 4) clearly shows the dissimilar nature of these polymer chains within their crystals. This feature leads to the lowering of crystal symmetry and thus the effective doubling of the unit cell volume of I as compared to 2. Despite these different rotation mechanisms however, the packing arrangements in their respective cells are such that nearest-neighbour interactions between thiazole ligands on adjacent

1848 M. James et al.

Br *

Fig. 3. An ORTEP drawing of linear chains of Cu(tz),Brz (2). H atoms are omitted for clarity. All atoms are represented by the thermal ellipsoids at 50% probability.

a

t C

<I o-2>

Fig. 4. Packing of infinite linear chains in the unit cell of Cu(tz),Br> (2). The chain direction is into the page (parallel to the b-axis).

Synthesis and crystal structures of di-bridged polymers

Table 3. Selected bond lengths (A) and angles ( ) for 2

cu-cLl* 3.987(3) Cu-Br 2.472(l) Cl--s I .698(4) Cu-Br* 3.120(l) s-c2 1.708(4) Cu-N 1.988(3) C2-C3 1.366(6) N-Cl 1.308(5) C3-N 1.369(5)

Br-Cu-Br* Cu-N-Cl cz-s-c 1 S-Cl-N Cl-N-C3 C3-C2-S

90.2(l) 124.2(3) 90.4(2)

114.1(3) I 11.4(3) 109.4(3)

Cu-Br-Cu* Br-Cu-N Br*-Cu-N Cu-N-C3 N-C3-C2

90.2(l) 90.0( 1) 90.1(l)

124.4(3) 114.7(4)

*An asterisk denotes a translation of the molecule along the h axis.

1849

chains are similar. Equivalent interchain relationships are observed along the (-101) direction in 1 (Fig. 2)

and the (l&2) direction in 2 (Fig. 4). With respect to the orientation of the thiazole rings, the interchain relationships in 1 between rings C, F and H (Fig. 2) are analogous to those relationships between rings I, J and M in 2 (Fig. 4). The interchain distances between rings in these structures are comparable, although those for 1 tend to be slightly shorter than found in 2 (Table 4).

Although interchain distances are similar for these two complexes, the position of chains along the b axis are different in each. Cu centres in 2 occupy high symmetry 2dsites (l/2, l/2,0 and l/2,0, l/2) in P2,/c, while Fe centres in 1 occupy general 4u sites (x, y, z) in Cc. The relative positions of adjacent polymer chains along the c axis of 1 are therefore shifted in h with

Table 4. Selected interchain distances (A) for 1 and 2

Ring Atom Ring Atom Interchain Distance

C F C F F C F E

I J I L L L

1

H6 F H2 Hl H H4 H5 F H3 H2 Cl1 Hl Cl2 H5 D Sl H2 s2 S2 F Sl

2

H2 J H3 Hl M HI H3 J H2 H2 Br H2 M S S M S

2.46(I) 2.53(l) 2.66(l) 3.04( 1) 3.29(l) 3.25( 1) 3.33(l) 3.39(l)

2.56(l) 2.62( 1) 2.67(l) 3.01(l) 3.27( 1) 3.64(l)

respect to one another, leading to a modulation throughout the crystal.

Magnetic susceptihilitJ

The molar magnetic susceptibility (xmo,) of Fe(tz)2Clz was measured at room temperature (298 K). Upon correcting for diamagnetism an effective moment &) was determined as 5.5 l(2) pB ; this value being consistent with high-spin Fe*+ containing 4 unpaired electrons (S = 2). Cotton et al. report a smaller effective moment of 4.90 pir for the di-chloro-bridged polymer [FeCl,(OPMe,)], [22], the reduction in mag- nitude possibly being a reflection of the trigonal bipyramidal coordination geometry. Due to the scarcity of pseudo-octahedral di-halide-bridged Fe(B) I-dimensional systems, very little has been studied of the magnetic response of these materials to changes in temperature.

The magnetic behaviour of 2, has previously been characterised [I ,5]. Room temperature susceptibility measurements were carried out by Hughes and Rutt [5] who found an effective moment consistent with the I unpaired spin of d’ CL?+ ions (,LL,* = 1.77 ,LL~). Variable temperature susceptibility data were collected by Estes et al. [I] and were able to be fitted by an isotropic Heisenberg model using the relations of Bonner and Fisher [33], giving ./ = - 10.4 cm-’ and 9 = 2.12. Interestingly, a good fit to the data for Cu(tz)zClz was found using a model for a two dimensional Heisenberg antiferromagnetic layer, however attempts to fit the Cu(tz),Br, data to this model were unsuccessful. The authors proposed that additional superexchange pathways via sulfur-sulfur contacts played an important role in the dimensionality increase of the chloride system.

The M-M distances observed in 1 and 2 of 3.717 A and 3.987 A respectively preclude extensive metal- metal bondmg occurring in these complexes, however the possibility of intrachain magnetic superexchange

1850 M. James et al.

pathways occurring via the di-halide bridges has been 18. clearly demonstrated in other studies [I ,2426,34-371.

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